Elliot Montanez
Elliot Montanez
30 Dec 2019

Turning the page into the next decade, our fourth edition of the “Top 50 Chicago Projects of the Year” list marks a special occasion. From the first list until now, four years means more than just four years of picks. It tracks four years of growth from some of our favorite artists, and a chance to watch last year’s entries rise up the ranks and improve, one year after the next.

This year, we’re welcoming several Chicago mainstays as well as a plethora of new faces. The constant between every pick? A strong representation of the talent in Chicago, solidifying the city as a front runner in the trend-setting landscape of hip-hop. If there’s any city presenting some of music’s premier faces, both old and new, it’s Chicago, just as we aim to capture on this list.

That said, below is Lyrical Lemonade’s top 50 Chicago projects of 2019. Thank you to all of the artists working so hard to provide us with music, and here’s to a promising decade to come for Chicago music. From 2019 ’til infinity.

Honorable Mentions: Chanelle Truvillion, Kiraly Payne

50) Josi Green & Ausar – The Good & The Bad EP

Josi Green and Ausar are certainly no strangers to our Lyrical Lemonade audience. The two artists have been staples in the underground and rising Chicago hip-hop scene for the last four/five years and they are just now hitting their stride, so when they connected earlier this year for a short EP titled The Good and The Bad, I had a feeling it would be a strong contender to make our year-end list. When it comes to straight spitters, not many from the city can go toe to toe with these two, but don’t think for a second that they lack melody or soul in their music, because they are masters of it all. One interesting aspect of this tape is that these two creatives have so much chemistry together that it came off so organic, and you can hear how familiar they are with each other in the way they bounce back and forth off of one another. Both Josi and Ausar always put each other in the perfect position to succeed, and this tape resembles just that.

49) Johari Noelle • Tycsol

One Chicagoan who I got the chance to learn more about this year was songstress Johari Noelle, who I interviewed back in May around the release of her project Tycsol (Things You Can’t Say Out Loud), and I knew even back then that it had a solid chance to get featured on this year-end list! Johari Noelle is a creative who didn’t start pursuing music seriously until her college days at Northen Illinois University, although she had some experience doing vocals on tracks for her friends at Homewood Flossmoor High School.

Now, in just a few short years, she has put herself into a position to become one of the city’s next best singers. A large part of her success comes from the release of this amazing five-song project. She crafted a sensational body of work here where each record is great, but the standout song on this tape (in my opinion) was the silky smooth joint titled “Too Much”. Ironically enough, this record was partially thanks to a confrontation that she had with a former co-worker earlier this year at her old job, and instead of caving to the negativity and causing a situation at the workplace, she held that energy in and brought it straight to the studio to put what she was feeling into the music. I foresee Johari continuing her upward trend in 2020 and beyond — she has a ton of talent so stream her project below before you continue on with the rest of the list!

48) Luke Almighty • Class Clown

Luke Almighty is one of the few producers on this list that really made waves with a full-length project this year. You most likely have heard his beat tag on some of your favorite local artist’s songs before and he’s only getting started. He takes the epitome of the Chicago hip hop sound and adds his own flare, allowing for a unique and always impressive offering every time he drops something new.

This year, his project Class Clown was truly a treat that not only fans enjoyed, but it was also a stepping stone in the right direction for his music career. He recruited a mixture of Chicago legends like Twista and Supa Bwe along with some bright young stars in CP, Heffy, and HateSonny among many other fantastic artists. What was most impressive was the fact that each song had its own narrative told by Luke through his production. Even though he didn’t say a single word, each and every beat created a different setting which allowed for all of the artists, whether they’re world-renowned or local up-and-comers, to share their thoughts and flows.

Some of the standout tracks include some lighter, cruising anthems like “Jump” and “Drop Top”. These songs create a crisp foundation for Duffle Bag Buru, Dutcho, and CP to showcase their individual styles and beyond-impressive rhymes. “Believe That” is definitely a more ominous cut that hits as hard as some of the classic drill music that comes out of the city, even though the style is clearly different. “Shoe Boxes” gives a very airy, almost tip-toeing vibe that paves the way for Bodi to sing a catchy hook and Twista to spit some rapid-fire bars like no one else can. 

HateSonny absolutely bodies his verses on “Brand New”, which features a creative and appealing sample not only on the hook, but consistently throughout the verses, as well. My personal favorite has to be “Sticks”, where J.R. Donato showcases an Atlanta-inspired flow containing clever wordplay left and right, which is all done over piano-heavy production full of banging 808’s.

Luke Almighty is only just starting out and his potential is insane. The way he can understand a certain artist’s style and adapt to them while also adding his own twist to get them out of their comfort zones is uncanny, to say the least. To see how great Class Clown was with mainly Chicago features was remarkable, and I can’t wait until he’s able to expand to bigger audiences and work with artists from other cities, as well. If you haven’t heard this project from the talented Chicago producer, add it to your list and give it a listen as soon as possible.

47) Sydny August • UNI EP

Way back in April, Chicago native Sydny August released a stellar EP titled UNI. It was a great body of work that only got better with time as the year continued, and I was sure that when I got around to making this year-end list that this project would be included. The EP takes us on a trip through Sydny’s deepest thoughts as she explores the hidden truths behind love and everything that comes with it. As you go through each song, you will instantly notice the amount of attention to detail that was emphasized in constructing this masterpiece. With only one feature throughout the 7 song project, Sydny proved that she has what it takes to become a head-turner in this game. I’m so excited for her future and what’s to come next for her — I highly suggest you stream this project ASAP! 

46) Mother Nature • Pressure

Mother Nature are some of the best wordsmiths to come out of the city in my opinion. Klevah Knox and T.R.U.T.H. flow better than a lot of the biggest artists in the music industry and their style is one of a kind. It’s honestly tough to think of any artist they sound like or to pinpoint their influences because they can sound totally at home on any beat that’s put in front of them.

Although the Pressure EP is only four songs and clocks in at around 13 minutes in length, it completely packs a punch. The duo sets a scene and paints their own narratives using each song as a blank canvas that they utilize perfectly. The opening track “Pressure” has a mystical sound, with out-of-the-box instruments popping up in the background as both artists spit masterfully and effortlessly. My personal favorite song comes up next, named “Dmn”. The production is haunting, allowing Mother Nature to deliver an ominous hook as well as a few different styles throughout the entirety of the track. The third song is called “Simple”, but it truly is anything but. The production boasts some deep chimes and heavy bass, but the rhyme schemes and lyricism are absolutely unbelievable. This leads us to the grand finale “Born”, which occasionally contains multiple vocal layers that sound as if there is an entire crowd rapping in unison. This track also comes off as more assertive than some of the other cuts off of the EP, which leads to hard-hitting bars that stick with you even after the project comes to an end.

Mother Nature truly has unlimited potential when it comes to their music. This duo can body any verse, have a very unique voice when singing, and can switch to different styles at the drop of a dime. All of these things put together can truly lead them to not only be some of the best female artists in the music industry, but one of the best duos period. Although this EP is relatively short, you’re going to want to play it on repeat after your first listen without a doubt. Check out the Pressure EP if you haven’t already and prepare to be mesmerized.

45) Ness Heads • Numb

One artist who I wasn’t familiar with back in 2018, but fully captured my attention in 2019 was Ness Heads, who released a noteworthy EP earlier this year titled Numb. It’s an extremely quick listen considering that the tape is just five songs in length and 12 minutes of playtime, but trust me when I say that she packed some great music into this EP — it has immense replay value and always leaves listeners craving more. Ness Heads emerged as a potential star in 2019 but I feel like this next year will be an even bigger step in the right direction, so do yourself a favor and don’t sleep on this one!

44) Sunny Woodz • Holy Sun

Sunny Woodz has been a staple in the Chicago music community for years now. He has helped grow and develop plenty of different Chicago-based talents and the perfect representation of that was his 2019 project titled Holy Sun. Sunny is an extraordinary producer but that’s no secret, and on this project, he used his platform to give multiple opportunities to dope rising artists — on this sixteen song tape, alone, he managed to feature nineteen artists! Sunny Woodz has been doing some tremendous work within the community and this year he pieced together an amazing project, which is exactly why he is landing at #44 on our list. Stream this brand new tape via Spotify below and give Sunny Woodz a follow here!

43) Sprado – Bases Loaded EP

Sprado is a Chicagoan who has been making some noise over the past couple of years. He first grabbed my attention after the homie Bekoe put me onto his movement, and I have been a fan of his ever since. Needless to say, I have been waiting anxiously for this project! The tape is a total of thirteen songs in length and it offers an array of different types of sounds from the young emcee, but don’t think that he strayed away from his signature style; if anything, this is just a well put together and more polished release from Sprado. I enjoyed all of the songs provided here but a couple of my favorites including the catchy “Mike N Ike” as well as “American Dream” featuring the Chicago OG Jeremih! This is a must-listen for any hip-hop fan but especially if you’re from the city, press play below!

42) OvaEast Meech • Saints II

Ovaeastmeech is an emcee out of Chicago who I have been supporting for damn near four years now. Last time I spoke with him, I was asking when he was going to bless us with a project, so when I saw he dropped a seven-track EP titled Saints II a few weeks back I was more than happy! Meech wasn’t solo for this effort though — he had his good homie and mega-talented producer Mic Lee right by his side for the entirety of this tape, and if you know anything about their connection together, you know they did something special here. I have grown to know Meech to be a great rapper, but even better when it comes to making ear-pleasing melodies that could become radio hits with the right backing. Here on this EP, though, you’ll find Meech getting a lot more introspective about adversities he has had to overcome. This EP is the second installment of Meech’s 2016 effort Saint, and his first project since 2017 if I am not mistaken, but trust me when I say that it was well worth the wait. Of course, I had to include this amazing EP on our year-end list, so, for the time being, stream this new tape via Soundcloud!

41) BoatHouse & Ajani Jones • One Punch EP

The art of collaboration is truly sacred. A rapper and producer’s chemistry in the studio and ability to bounce ideas off one another is undoubtedly the secret ingredient to many collaborations that we herald today. This intangible quality is what makes the team-up of BoatHouse and Ajani Jones so special. The duo’s collaborative EP, ONE PUNCH, is five tracks of in-your-face lyricism and even more aggressive production. Song’s like, “SAITAMA,” FUTURAMA” and “APEX” are unrelenting in their mission to shock while “NATIVE SON” and “PRONTO” find Ajani Jones reeling in his speed to match the more laid-back sensibilities of BoatHouse’s production. The tape, in its entirety, is awe-inspiring; the tandem between Ajani Jones and BoatHouse is one of the most exciting and effective collaborations we have seen this year. Anyone can hop in a studio and work together, but it takes a true undefinable quality to create something as special as ONE PUNCH.

40) Wemmymo • 10:15

Chicago talent Wemmymo recently celebrated his birthday on October 15th and he was kind enough to gift his fans with a present to represent that day, and we were blessed with 10:15. If you are in tune with Wem, then you know he always incorporates some sort of comedy sketches into his music, and this tape kicked off with a comedic skit that plays around the idea of Wemmy playing his new project in an Uber, avoiding an overzealous conversation with the driver in the process. The next seven songs provided were exactly what I was expecting — a nice mixture of well-put-together tracks with tons of melody and moments where Wemmymo delivers nothing but straight bars, not to mention giving other artists a chance to shine with the features he handpicked. I’ve already run through this entire tracklist at least a few dozen of times through, so trust me when I say that this was one of the best underground tapes that we received out of the city this year. Stream this brand new project via Spotify below and if you like what you are hearing from the young Chicagoan, then go ahead and give him a follow here!

39) Lexi – With Love, Lexi

When I first got started writing for LL about five years ago, one of the first artists that I met in the Chicago music scene was Lexi — a mega-talented singer that I met in a bedroom studio at my homie Lil Jake’s parent’s house where she was singing vocals on a track, and I quickly realized that she was better than most people her age. I then learned that she had tons of experience in Chicago’s Children Choir where she honed and crafted her skillset, and she eventually continued to pursue her music journey in college, but unfortunately, she wasn’t releasing any music at all for a while.

For a few years, I wondered when she would release more music but more specifically, a full-length project or EP, and luckily, earlier this year, she blessed us with a fantastic body of work simply titled With Love, Lexi. The five-song EP was certainly one of many standout tapes to come out of Chicago this year. Not only was her vocal performance clean and spot on, but she created some records on here that show the potential of an artist who can make radio hits in the future. The sky is the limit for Lexi and I picture her having tons of success in the future, so if you aren’t yet familiar with her, stream her project below before you continue on with the rest of the list!

38) Twista • Summer 96

Featuring a picture of Chicago on its cover, Twista’s Summer 96 brings fans 15 new tracks from an undeniable Chicago legend. Taking things back to 1996, it’s a time capsule into the days when Jordan was on top, and the music hones in on this nostalgia, packaging it in an entertaining manner even for fans of the current generation. Rappers don’t always age well, but Twista’s unmatched rapping skills haven’t faded, and his 2019 project was a strong chance to prove it.

37) Bianca Shaw • Exhale

Bianca Shaw has been building up a solid career for herself over the last few years; she has made her name well known within the Chicago community, she has established a core fan base, and earlier this year, she released a fantastic new EP titled Exhale. This seven-song project found Bianca Shaw delivering some of her most enticing flows, showing off her always stellar vocal abilities, and overall, it was just a great display of the talent that she possesses. Be sure to look out for one of Chicago’s most talented up-and-comers by streaming Exhale below!

36) Matt Muse • Love & Nappyness 

Matt Muse is an emcee out of Chicago who has been something like a staple in the city for well over half a decade now, and earlier this year he released his best body of work (in my opinion) titled Love & Nappyness. It’s a thoughtful, well-pieced together and intelligent project that only someone like Matt Muse can create. He speaks on several topics that all have to do with different types of love. Matt Muse showed off his always-excellent lyrical ability plenty of times within this tracklist — he spits with a certain type of grit and style that can only be bred here in the city, so much so that Matt truly embodies what being a Chicago creative is. I am proud of the year that Matt Muse has had just as a fan and a music lover, and I see nothing but big things for him in his future. Stream this excellent project below and if you’d like to learn more about Matt Muse, then go read up on the interview we did with him earlier this year here!

35) Jack Larsen • Mildew

In 2018, Jack Larsen made our Top 50 list with his debut EP, Push-Ups. Now, in 2019, he’s back with his most successful project thus far, Mildew. Bringing his world into notably weird and experimental waters, Mildew felt as though it was the purest vision of Jack Larsen’s world to date.

Born from a fever dream-esque period when Larsen was sick from a mold-born illness, Mildew cashes in on rich instrumentation and feverish, genreless energy. It’s a journey of a project, and certainly one of the more memorable releases of the year, making sure to stick out amongst the noise that often crowds the space for new releases to breakthrough. If there’s any way to stick out, it’s to be yourself, just as Larsen has proven with his renowned 8-track effort.

34) Alex Wiley • Tangerine Dream II

To build a cult following as a rapper is probably one of the most sought-after aspects of getting into this industry. Not all rappers can do it and even fewer have tried, making the exceptional career-long run from Alex Wiley even more impressive. Following the same thematic ideas that birthed his project series, Alex Wiley’s follow-up, Tangerine Dream II, finds the rapper picking up where he left off. Jam-packed with hazy references, intergalactic metaphors, introspection, and spaced-out production, Alex Wiley captains a stellar journey through the smoked-out cosmos. Listeners will find themselves lost in the vigorous cadence of “Life One,” entranced by the sweeping strings of “Very Close,” and ultimately spellbound by the smokey delivery of “Move Around.” Songs like “Something More” and “Quarter to Four” help build on the reeled-in aesthetic Wiley has created for himself on countless outings. At 12 songs, spanning a total of 29 minutes, Alex Wiley manages to engulf listeners in his tangerine-colored world. Fingers crossed we get at least one more installation of the Tangerine series!

33) Reeseynem • Only On The Weekends

Aside from releasing a single or two in both 2017 and 2018, this year was really the first year that Chicago’s own Reeseynem released music, and with that, we received his debut project titled Only On The Weekends. Reeseynem has been a well-known figure within the city for some years now and he really took the music scene by storm especially with his smash hit record “What’s The Hook” featuring his right-hand man Chance The Rapper, but he continued to impress the masses with this debut tape, offering a variety of different sounds that hold something for any kind of listener. This project felt something like a family affair when you look at the tracklist and all of the features, as you’ll see plenty of familiar names such as his Savemoney partners KAMI and Joey Purp, Taylor Bennett, Forever Band, Lil Danze, Jeremih, Supa Bwe and more! Considering how early in his musical career, I only see Reese continuing to improve as an artist and providing us with more ear-pleasing hits in the years to come. For the time being, though, stream this stellar 2019 project below.

32) Qari & Greensllime – Operation Hennessy

Over his career thus far, slept-on Chicago staple Qari has proven to be endlessly consistent, from his early work as 1/3 of the group Hurt Everybody, to his standout solo tape No Time to Explain which made waves last year, to his collaborative projects with producers. Operation Hennessy reasserts this penchant for tongue-twisting, quick-witted consistency supercharged by production from fellow Chicago scene veteran Greensllime. The two artists work in tandem to craft a dreary tape that seems to be stuck in a midday stupor — the type of project you play on days when you just can’t seem to leave the house, stumbling around to Sllime’s irregular sample chops underlaying Qari’s tangentially tangled flows.

Operation Hennessy exudes a sort of effortless finesse, a quality that befits both Qari’s and Sllime’s musical M.O’s. They both thrive off the motif of unforced creativity. This quality manifests in Qari’s laidback presence at all times, and even when he opts for a more agile flow on tracks like “Argonaut”, his unhurried delivery and gravelly tone naturally roll off the tongue. Greensllime’s uncanny ear for ambient sounds further sets a dizzying environment that resonates throughout the whole record, and he stitches each track together in a remarkably cohesive way. Interludes ripped from Wes Anderson’s The Life Aquatic with Steve Zissou form a constant through-line as the tape progresses, functioning as thematic inspiration for the project both aesthetically and lyrically as it’s referenced multiple times throughout.

Operation Hennessy isn’t the type of rapper-producer project that hits a listener over the head with one-off bangers or high-octane energy fused between the two artists. Instead, Qari and Greensllime opt for a more subtle, easygoing vibe that sits right in each of their wheelhouses. With that tone set, they proceed to do what they each do best, making for a memorable collaborative project from two of Chicago’s finest.


31) Myquale & Thelonious Martin – XX Winters

Myquale’s XX Winters EP closes out somewhat of a breakthrough year for the quickly rising rapper, coming off the heels of a streak of consistent singles and last year’s promising Flight Theory project which introduced many to Myquale’s versatile talents. XX Winters follows up on that introduction with an even more fleshed out vision of the songwriter’s artistry, complete with enough mind-bending flows and clever double-entendres to impress even the most astute rap purists. Myquale doesn’t just serve up lyrical excellence on this project, but he also distinguishes himself from the pact through easygoing melodic breaks and a mellow tone in his voice that makes it difficult not to get instantly hooked.

Myquale connected with Chicago producer Thelonious Martin on this project—a match that ultimately brings out the best in both artists. Martin’s jazz-influenced beats and deft sample chops form a strong foundation for Myquale to make piecemeal of, finding infinite flows in the warped instrumentals and squeezing words in between blasts of live percussion leaving little room to breathe. The tracks themselves are mostly autobiographical as Myquale dissects aspects of his upbringing, his current place in life, and his shifting mental state. In between, he sneaks in sharp jabs at his competition and carries himself with the self-assured bravado of a seasoned veteran. His boasts get balanced out by bouts of utter self-awareness, steeped in what could only be the sound of years of honing one’s craft. XX Winters makes for yet another impressive release by one of Chicago’s new promising talents—one who will likely end up on this list again in the future.


30) BJ The Chicago Kid • 1123

If one thing is for certain, when it comes to BJ The Chicago Kid, he has made some of the most soothing, glorious, and ear-pleasing music that the city has had to offer this decade. Earlier this year, BJ The Chicago Kid released a fantastic tape titled 1123 — a sixteen-track project that contains some of BJ’s best music to date, in my opinion. When I first heard this masterpiece, I just knew it had to be included on this piece. BJ The Chicago Kid is a one-of-a-kind talent that might straight up be the best R&B artist that the city has to offer — if not, he is for sure top two, and anyone who disagrees with that just simply needs to run through this tracklist one time to hear what he is all about, as I assure you that he will win you over.

29) Queen Key • Eat My P*ssy Again

Chicago’s Queen Key embodies an artist who only seems to get better as her name gets bigger, and her 2019 tape, Eat My Pussy Again, serves as a testament to her majesty’s come-up over the past year. Don’t be confused by its title—Queen’s latest project is twice as long and anything but redundant when compared to its predecessor, 2018’s Eat My Pussy. Instead of merely just repeating the same formulas that allowed the rising rapper to find early success with her previous project, she builds upon the elements of aggression, sex, and conviction to even further distinguish her own voice.

The self-proclaimed “female money making Mitch” serves up an endless supply of memorable one-liners on every track, and in between her slick self-assurance, she backs up her cockiness with testaments to her own hustler’s mentality. As a result, Queen Key finds her stride and stays in it throughout the entire project. The energy level only increases, and her flows stay sounding fresh over a range of beats from producers like Izell Stanton, Apostle, Marious Banks. The beat selection on this project tends to lean mostly in the hard trap hip-hop direction — a consistent complement to Queen Key’s naturally menacing presence over the instrumental. But the mixtape takes an unexpectedly sentimental moment on the track “I Like Me Better”. Just when Queen Key’s “sound” seems to be pinned down, she gives a glimpse at a more vulnerable side of her character as a rapper. It’s a track that caught me by surprise the first time I heard it, and a moment that leaves the door wide open for what else the artist has up her sleeve.

28) HappyBirthdayCalvin – No Friends EP 

HappyBirthdayCalvin burst on to the scene with his hit single “No Friends.” The No Friends EP served as Calvin’s major project debut as it was released under LA Reid’s HITCO imprint. I actually believed that Calvin’s “No Friends” single would’ve even blown up even more, as the song title screams viral and was making some headway on the viral charts on Spotify in the United States. On this 3-track project, the other two singles, “Anything” and “Willow Tree,” aren’t quite hits like “No Friends”, but are formidable records in their own right. “Anything” serves another anthem type single similar to what “No Friends” embodies, while “Willow Tree” is more of a toned-down record that sounds similar to a Travis Scott track. If you have 10 mins to kill, you should give HappyBirthdayCalvin’s deeply-promising No Friends EP and form an opinion on it for yourself.

27) Ajani Jones • Dragonfly

Ajani Jones is one of the brightest rising talents that I have had the pleasure of covering over the past couple of years. He has become one of the new faces of the city’s scene, and a large part of this is thanks to his 2019 effort titled Dragonfly.

He furthermore proved that he is unlike any artist with this tape, thinking of a unique concept/idea and executing it perfectly, consequently creating a fantastic project from start to finish. Ajani is one of those guys that I would keep an eye on if I were you, as he has the potential to be one of Chicago’s leaders in this music community in a few years, and this new tape is just another step in the right direction for him. Stream this brand new project via Spotify below and if you enjoy what he put together then go ahead and follow him on Twitter here.

26) Lil Reese • GetBackGang 2

A staple of Chicago drill ever since the genre’s emergence at the start of this decade, Lil Reese has been steadily moving into the spotlight over the past few years as his own artist aside from his collaborations with the likes of Chief Keef and Lil Durk. GetBackGang 2 furthers Reese’s reach as a solo artist, building off the first edition of the mixtape which came out last year.

Reese avoids sounding dated, instead coming off as refreshed on this tape over a breadth of both aggressive and introspective songs. Authenticity cements every word that comes out of Reese’s mouth, and the genuine, unguarded descriptions of the rapper’s lifestyle get delivered through memorable hard-hitting verses. The two featured artists on this project also speak to Reese’s legitimacy, with one contribution from Chief Keef and the other a posthumous verse from Fredo Santana. All throughout the project, Reese leaves the listener with songs that are equal parts menacing and motivational—a continuation of what attracted the world to drill in the first place and a promising mark of the artist’s own progress.

25) Kaina • Next To The Sun 

KAINA’s career has been slowly building to the release of Next to The Sun — the versatile songwriter’s debut album. Her musical momentum could be traced all the way back to her earliest involvement in the local music scene, and along the way, she’s crossed paths with some of the city’s most prolific musicians. Next to The Sun, then, can be viewed as the product of those formative years and the first cohesive chapter of KAINA writing her own story.

This personal narrative comes in the form of songs that are unafraid to diverge from a traditional structure, and instead, seem to bend to the songwriter’s emotional will in a way that flows straight from the heart. KAINA does not seem satisfied with surface-level explorations of her own psyche on this project, delving into deeper musical analyses of her personal struggles, the ways she has come to give and receive love, and the strength of her most cherished relationships. Pervading her own self-awareness is an overarching acknowledgment of the greater moment we all live in, but these moments of greater awareness never serve to overshadow KAINA’s own voice; they ground her unique personal experiences in a way that makes them universally relatable for a listener.

The product of a true student of the Chicago music scene, Next To The Sun announces KAINA’s turn to take center stage, accompanied by unbridled songwriting and compositions that roar without the need for making unnecessary noise. KAINA makes every minute of her full-length debut purposeful, making sure to make each moment a part of her story and reassuring listeners that she’s far from finished telling it.

24) Common • Let Love

I have been a huge fan of Common since I was just a kid. His music has been something like a soundtrack to certain times in my life, so I was eager to hear what this new project sounded like when it dropped earlier this year. Well, over the past couple of months, I have had this album on repeat, as it’s easily one of my favorite albums of 2019 and a standout from Chicago in 2019. He rhymed over some amazing, soulful instrumentals on this eleven-track tape, and even gave us a part two of his hit record “I Used to Love H.E.R.” as well as other touching songs like the ode to his mother on “Forever Your Love”. Common has released some classic albums over the years, and I believe that this new project will too stand the test of time, so bravo to Common for putting his best foot forward. If you haven’t already checked out this album, give it a spin via Spotify below!

23) The O’My’s • Above Ground EP 

Certain artists are synonymous with quality. The mere utterance of their name calls your senses back to projects, singles or even music videos that exceed the bar of exception. Any list of these artists would be ill-conceived without the inclusion of The O’My’s and their stellar combination of R&B/Soul. The O’My’s, collectively made up of Maceo Haymes and Nick Hennessey, have long proven their ability as musicians and passion for the art form. To no surprise, the group’s six-track EP, Above Ground, is incredibly difficult to put down.

Whether you are intoxicated by the song’s sticky-sweet opener, “Summer Jam,” or lost in the chameleon-like orchestration of “Space Bounce,” The O’My’s manage to find several ways to serve our senses on their sophomore release. Tracks like “Strawberry” and “Luke’s Song” pull on your heartstrings while “Mood” relishes in more sinister energy. The group’s musicality is unmatched by many and is always delivering timeless music in new and creative ways. The O’My’s remain undeniably crowned as one of the most talented acts to emerge from Chicago.

22) Rockie Fresh • Destination

One release that I was looking forward to all year got released about a month or two ago, as Chicago native Rockie Fresh put out his new album titled Destination, his first album since 2016. Rockie Fresh has been one of my favorite artists in the city’s music community for years now and I (as well as many others) were patiently waiting for this release, especially once the singles and rollout began earlier this year. I’ve been thinking that this could potentially be one of his best, if not his best project to date, and after listening to the final product multiple times through over the past several weeks, it’s safe to say that my hunch was right.

I thoroughly enjoyed all of the tracks provided on this album, but my favorite one is probably the intro record “King’s Back” because of the energy and emphasis that Rockie put into that song. Although, a close second has to be the melodic jam that is “2 Late”. Stream this brand new album below to get in tune with one of the most talented Chicago OG’s below — I assure you that you will not be disappointed.

21) Valee • Runnin Rich

One of the most pleasant projects to be released this year comes from the unmatchable charisma of Valee. The Chicago rapper’s 2019 project, Runnin’ Rich, packs a hardy helping of all the things that make Valee one of the standout artists from the city. It is incredibly hard not to catch a vibe on this project with the stunting nature of “Ice Attack Prequel,” “Above Average,” and “Sleep Number.” Regardless of what tempo Valee utilizes, the Chicago wordsmith finds some way to pack a medley of quotable lyrics in his sauce-laced flow. Despite the constant attempts to replicate this artist’s sound, others merely fall to the waste side, unable to capture the energy Valee has on each of his records. There is only one Valee, and his eight-track, 17-minute demonstration on Runnin’ Rich continues to cement that there will be no one else like him. 

20) MFnMelo • Everybody Eats

As the clock winds down on an already impressive year for Chicago’s Pivot Gang, the group couldn’t let these final weeks pass without one more memorable release from within its ranks. Today, MFnMelo steps into the spotlight with his debut album, Everybody Eats. The first project from Melo since 2017’s Melodramatics features help from the Chicago native’s close circle of local talents and offers up the most comprehensive catalog of Melo’s own talent yet.

Packed with Melo’s mix of personal narrative, sense of humor, and cunning wordplay, he distinguishes himself by putting his own authenticity at the fore of Everybody Eats. As a member of Pivot who’s worked relatively in the shadows up to this point, Everybody Eats feels like a moment of transcendence into the light, as Melo employs all the tools at his disposal with the polish of a seasoned veteran. He delivers melody on multiple hooks throughout the project while seamlessly transitions back to the weighty, definitive rapping that places emphasis on his every syllable. Each lyric gets executed with its own burst of air as if he’s vying for a listener’s attention every second, and he holds a listener there with him the whole time through a sea of constantly-shifting, head-turning flows. That is, not to mention the fact that he sets the tone for the rest of his collaborators to punch at the same velocity, bringing out the best from Chicago favorites like Qari and Mick Jenkins and producers daedaePIVOT and Monte Booker who deliver some of their best verses and beats all year.


19) Warhol.ss – M.I.A

Just a couple weeks before the release of this year-end piece, Chicago legend Warhol blessed his growing fan base with his brand new EP titled M.I.A. Warhol has been a staple in the Chicago music community for the past five-plus years; he was something like a teenage prodigy around the period he first starting coming up in the city, and now he has grown to the point where he is a well-known musician all over the world. His sensational music has been a reflection of his growth, and this new EP is truly some of his best work yet.

From the jump, Warhol came out with a fantastic intro record that set the tone for what else was to come, and as the tracklist progressed, he only got better and better. The only features on this EP came from Ugly God and Famous Dex on the third and fourth track, and each of those artists has had great chemistry with Warhol for a minute now, so of course, they made some magic. Each of these six songs provided are hits, and it’s only leaving me and many other Warhol fans hungrier for his next full-length project, hopefully coming in 2020.

18) Duffle Bag Buru • Fly On The Wall

If there’s one thing that we know about Duffle Bag Buru, it’s that he is big on energy. Energetic beats, energetic bars, and energetic personality—there is never a dull moment when Buru is on the track or in the vicinity, period. Despite delivering a handful of singles, his EP Whole Bag, and a handful of features here and there, Buru hadn’t prepared a full-length project until this year with the long-awaited release of Fly on the Wall. One of the most dominant rappers of the Chicago rap scene, Buru is known for remaining true to that gritty, hardcore-sounding rap. From his production choice and his signature raspy flow, he was no stranger to finding his pocket and staying in it to define his true talent as not just a rapper, but an artist.

Kicking the project off right with “Again”, this track sets the tone for the project, delivering catchy flows and mesmerizing 808’s that are guaranteed to keep listeners satisfied. With features from Warhol.SS, Slim Santana, Femdot, Ronsocold, and The Good Perry, Buru does not disappoint at all despite this being his first full-length project. Chicago has always been a city that delivers a new sound every few years, and Buru has made it clear that he is more than able to adapt to the current sound of the scene. That being said, Fly on the Wall is more than great of an introduction to what Duffle Bag Buru has in store and what he’s able to bring to the table of rap music going forward.

17) Chief Keef • Multiple Projects

Out of all the people included on this list, almost none of them can say they’ve changed the rap industry as much as Chief Keef. Ever since coming onto the scene as a young 16-year-old kid, he became known as one of the pioneers of the drill subgenre and he brought a completely new style and sound to the world of drill that was unheard of up to that point. He immediately had doppelgangers and people trying to copy him, but he stuck to his roots and kept making music like no one else was as the time. This led to one of the most iconic albums in my book, Finally Rich, which still sits in playlists all over the country and contains classics that put Keef on a national scale. Although it has been hard to keep up to date with the myriad of projects, EP’s, and mixtapes that Keef has released since that album, some of them are absolutely worth checking out and some of his projects from 2019 are a great place to start.

Starting out the year strong, He released The Leek (Vol. 7) — an entire tape that would please the old Chief Keef stans for the most part. Everything from the production to the vocal effects sound like it is somewhat compiled of songs that didn’t make it on Back from the Dead, one of his greatest projects of all time. Now, I don’t think that this tape compares in most ways to the classic mixtape, but it contains songs that could probably help classic Keef fans get back into his music after being away from it for however long they were. Don’t believe me? Turn on “Zero to 250” and try to argue that point, because it sounds like it could’ve been recorded in 2011 and sat in the vault ever since.

After that early mixtape released, he hit the studio with the hitmaker Zaytoven, and the duo decided to put some of their work together to release a collaborative mixtape by the name of GloToven. This 12-song project is just refreshing, to say the least, considering Keef has always been experimenting with different styles. The overall vibe of this project isn’t so outrageous that it’ll turn away classic fans, but it also offers a new take on his classic music that only Zaytoven seems to be able to bring out of the artists he works with. Some of the lighter and brighter standout cuts off of Glotoven include “Ain’t Gonna Happen”, “Fast”, and “Spy Kid”. These songs have a bubblier vibe with heavier autotune and more of a focus on melodies than some of the other tracks. He also seems to get more serious about some of the heartache he’s faced over the years in one or two of these selections, while still tapping into his roots during certain moments throughout.

“Batman”, “F What the Opp Said”, and “Posse” should please the older fans of his, because although they don’t sound exactly like old deep cuts, they offer a new yet nostalgic take on his older music. Along with this, he adds a new splash of style that bridges a gap between his classics and the latest sounds he’s been creating. Out of the entire project, my personal favorite song has to be “Sneeze”. You can hear the fun he’s having while recording, from the inventive lyrics to the melodies he creates, and his experimental flows to the overly-autotuned ad-libs, I enjoyed this song from start to finish.

I’m not entirely sure why but in May of this year, Keef decided to also rerelease his and Zaytoven’s Camp GloTiggy tape that originally dropped in 2016. This time around, however, he omitted many songs, cutting it down from the original 18-song soundtrack that it used to be to only 13 tracks this time around. Not only that, but he pinned two new cuts to the very end with “Old Heads and Regretful Hoes” and “South Side”. Both of these tracks have really nice beats with the piano-forward sounds that Zaytoven has become known for over his incredible career thus far. “South Side” is worth the listen more so than its predecessor, but if you haven’t listened to Camp GloTiggy since 2016, the rerelease is definitely a nice refresher with the bonus of some previously-unreleased hits.

After GloToven and the rerelease of Camp GloTiggy dropped, he wasn’t finished by any means and released another volume to his extensive The Leek series to bring the total up to 8 mixtapes. Out of all the projects he released this year, this one honestly had to be the most unimpressive in my opinion. It seemed like it was just released to hold people over, which seemed to be the strategy since The GloFiles Pt. 3 released later in the year. If you’ve listened to every single other project that Keef put out this year, then I’d say go for it and check out The Leek (Vol. 8), but unfortunately, I wouldn’t say this one’s a mandatory listen.

To round out the year on a good note, he dropped The GloFiles (Pt. 3). This project seems to have an all-encompassing feel to it, with various songs that do their own independent jobs to provide a little taste of everything that Chief Keef has to offer musically. With the overly-autotuned track “All In”, fans can hear the drill legend sing for over seven minutes on a high-hat riddled beat that brings back some memories from past years. With the next track “Thotty Party”, he brings mellow, laid back verses in which he discusses just how long he’s been in the industry for and how successful he is. With this song, it seems as if he knows that he doesn’t have to brag anymore because everyone knows these accomplishments and he’s getting tired of repeating them again and again. On songs like “Redbull”, “Shorties”, and “Tec”, he gets experimental again with both his voice and delivery itself, and also tests himself with some of the beats he selects to use. A lot of those beats have crazy drum patterns that at times caused me to lose the rhythm, but then would pick back up and surprise me with just how good they actually ended up sounding, to be honest. I believe The GloFiles (Pt. 3) was the lengthiest project he released all year, and although there are some songs that probably could’ve been left off, it’s worth checking out eventually.

Chief Keef had quite an eventful year in terms of music releases, but compared to other years where he’s dropped six to nine projects, I guess 2019 could be considered a slow year for him. In my opinion, the best project he released all year was The Leek (Vol. 7), which was also the first project he released all year. As the year progressed, he definitely had some hits and some misses, but either way, pretty much all of his projects are worth checking out at least once. Throughout all of these tapes as well, he had a total of less than five features, which shows that he’s carrying a lot of the workload, so some misses are bound to release at some point throughout the year. He has been teasing Almighty So 2 throughout this year as well, and that’s expected to drop at some point next year, so we’ll see if he has any more projects in store for us before then or if it’ll be the next new music we get from the Chicago icon. It’ll definitely take some commitment on your part, but take some time before 2019 ends to try and knock out some of these projects because I guarantee there has to be something in this pile of music that can, and will, appeal to you in one way or another.

16) Taylor Bennett • The American Reject

We are living in a world where negativity is all around us. Social norms and all tend to shape the minds of youth and all those alike. However, Chicago’s own Taylor Bennett released the third project in his EP trilogy which all tackled the theme of self-reflection, putting differences aside and uniting, and being true to yourself. During our interview with Taylor earlier this year, he stated that the main purpose of The American Reject was the understanding that “all of us are rejects and we really all don’t belong, but that’s a part of being unique, different, and standing out”. Everything from the content to the album, the title, and even the cover art stays true to the overall concept that Taylor had in mind, and that is something that has to be praised and appreciated in this current state of hip-hop. Across the span of eight tracks, Taylor was able to keep his message persistent throughout the entire project and deliver the perfect close to his EP trilogy.

As if his previous Be Yourself project was not ground-breaking enough, The American Reject continues that same reputation and Taylor delivers nothing but quality production, deep connecting subject matter, and an overall call to action. Gathering features such as Femdot, Ty Dolla $ign, and Mr. Hudson, Taylor delivers nothing but musical bliss. With so much going on in today’s society, this project was well-needed and well-appreciated for all that it stands for going forward. Whether you have not found yourself, are in the process of finding yourself, or already understand your purpose, this project is guaranteed to have something for you.

15) Jean Deaux • Empathy

There is no way we could make a list of the top 50 projects released from Chicago artists without including the incredible stylings of Jean Deaux. Her 2019 album, Empathy, is a resounding exhibition from the ever-evolving artist. Filled with moments of soaring vocal displays and precise lyrical implementation, Jean Deaux seems as sure of herself as ever. Fans of Deaux have known from the start of her rapping ability but many were probably unaware of her strength as a singer. Empathy does an incredible job of proving that Jean Deaux has the singing chops to serenade as well as lyrically deconstruct. Song’s like “Higher Me,” “Anytime” and “Life Lines” standout as impressive vocal displays while “Break Time” and “Ackin Funny” show Jean Deaux finding a pocket amidst upbeat glitch-hop production. The project in its entirety is beyond impressive, acting as a stern reminder of Jean Deaux’s prowess as an artist. 

14) Pivot Gang • You Can’t Sit With Us

Many of us know the separate individuals in Pivot Gang and many of their own albums have been featured in our best albums in Chicago’s lists over the years. Rappers Saba, Joseph Chilliams, Frsh Waters, SqueakPIVOT, MfnMelo and producers daedaePIVOT, and Dam Dam make up this Chicago rap collective. With group compilation albums, the main element that has to be present for me is great chemistry and synergy. Fortunately, Pivot Gang’s You Can’t Sit With Us checks off those two boxes along with many others. With compilation projects like this, usually, there’s an MVP of the record that shines. The easy answer would be to say Saba as he’s the most known and probably has the highest ceiling out of the group. However, I’m going to go with Saba’s brother Joseph Chilliams for my MVP on You Can’t Sit With Us. His flow and verses really made me want to go back and listen to his past work and has me looking forward to his next solo effort.

13) Cdot Honcho • Kingpin

Cdot Honcho is one of the rappers on this list that doesn’t just deserve more recognition, but he needs to be shown more recognition and respect in general. His talent is one-off, and his sound is quite possibly even more unique. He doesn’t copy anyone else in the slightest which can be rare in the music industry nowadays, and it’s even hard to think of any influences he might look to considering he really is so one-of-a-kind. From his interesting voice, to the production he so carefully picks, to the cadences and energy-filled verses he consistently drops, I’m not sure that there’s anything he can’t do.

Cdot’s versatility and multifaceted talents are showcased on Kingpin, the project he released just a few months ago. He goes from destructive and aggressive on certain tracks to thoughtful and reminiscent on others. Although the majority of this project is right up the alley of the former, the songs that are included in the latter divide up some of the hecticness throughout this half-hour long album. Some of my personal favorites include the opener “Kingpin”, along with “NBA”, and “Too Fast”.

“Kingpin’, which obviously boasts the same name as the record itself, is the perfect introduction to the world that Cdot is painting. This assertive hit shows off some of his fast-paced and uncharacteristic rhymes, getting the listener ready for the rest of the album. “NBA” is an earie, minimal, and bass-heavy offering that so many rappers have attempted to create recently, but few are as successful as Cdot is in this track. He even shouts out Lyrical Lemonade which is definitely something that can’t go unnoticed. “Too Fast” is a spectacle on its own, and the beat sounds like something out of the future. On this banger, Honcho seems to rarely breathe, if at all, and the fact that there are so many words coming out of his mouth during certain stretches of the song, I wouldn’t be surprised if he passed out after recording.

Some of the more meaningful tributes on this project include “Down”, “Quiet Storm”, and the closing track, “Vision”. These songs show us a deeper and more introspective look at Cdot’s life and perspectives, which is something that doesn’t happen extremely often, so when it does, it deserves to be appreciated. One of the most impressive things about this album is that it only contains one feature, which NLE Choppa does the honor of providing. He does this on “Warning”, which is quite possibly my favorite song off the project. Although it’s very hard to match Cdot’s energy on any track, Choppa is able to do so on this one, unleashing an absolute hit.

Cdot Honcho has proved time and time again that he deserves more credit than he gets, although this doesn’t seem to bother him. He seems to be happy with the success he’s earned, but he’ll always be striving for bigger and better things no matter where he might land in his career. It’s never easy for anyone to consistently release the quality of work that Cdot drops, so the fact that he rarely, if ever, has any miscues is beyond impressive. Kingpin is 100% worth the listen and if you disagree for whatever weird reason, your taste in music might just come into question as far as I’m concerned.

12) Supa Bwe • Jaguar EP & Just Say Thank You

Few artists could make an entire career off of being an unpredictable wildcard, but through the years, Supa Bwe’s proved to be at his best when he defies being pinned down and pigeon-holed. Even looking at the two projects that the Chicago hip-hop provocateur dropped in 2019 alone, it’s clear Supa’s not giving up on confounding and surprising listeners with the breadth of his musical capabilities anytime soon. It’s sometimes hard to believe that the ambient, experimental-R&B Supa that surfaces on ‘Just Say Thank You’ and the feral, flesh-eating ‘Jaguar’ version exist in the same world.

But alas, it’s undeniable that both these personas have been conjured up by one artist, and the qualities that do consistently manifest throughout Supa’s discography appear even more poignantly when he’s pushed to his most experimental extremes. Even at his wildest, Supa’s endearing spirit continues to ground his music in humility and vulnerability. Amid the sirens and screams on the song “LOOK”, there’s a narrative of Supa fending for himself in the reality of his own wilderness. He also fully leans into his vulnerable side at times, and ultimately finds success when he does so on tracks like “Rememory”. This nostalgia-trip of a song might come off as uncharacteristically tame for Supa at first, but something about his punk-ridden vocal quality and the unguarded desperation in his flows only echo the sound of a spirit that refuses to be contained (not to mention the song also contains one of Chance’s best verses in recent memory).

Over the years, Supa’s maintained somewhat of a cult-like fanbase of loyal listeners who have witnessed the artist’s constantly shifting but always true-to-character evolution. Just Say Thank You and Jaguar offer the latest iterations of that evolution to satiate his growing, dedicated following while enticing new listeners to join the club.


11) Kembe X – I Was Depressed Until I Made This

I Was Depressed Until I Made This is a project that absolutely deserves a spot on this list, but it might not be as evident to music fans outside of Chicago until they actually give it a listen. Kembe X has been a bit of a local legend for years now and has had glimmers of success outside of the city, but no one seems to appreciate him like we do in Chicago. This is quite unbelievable considering how consistently strong his projects are time and time again, and I Was Depressed Until I Made This is no exception in the slightest.

With a wide range of styles including heartfelt singing as well as unmatched rapping, this project is an absolute hit. It starts out very strong with some more high-spirited rap cuts like “859” and “LFTFF” which really allow him to put his different flows on display. These tracks are followed up by soulful and more profound ballads like “Body Language” and “Roblox”. One of the hardest songs on the entire album has to be “Scoreboard”, where Kembe shows off yet another style of his, which is a bit more aggressive than we’re used to hearing from him, but also continues to feature some incredible references and wordplay that is always something that fans of his can rely on.  The song on this album that I think could have the most mainstream appeal considering its catchiness and soulful vibes has to be “Voices”. This track has it all, from the variety of musical gifts Kembe possesses to the relatable messages and stories he narrates throughout.

Outsiders that aren’t from Chicago always look at the city as if drill is the only type of music that artists create here, but Kembe X is a prime example who not only challenges this theory but full-on disproves it. I Was Depressed Until I Made This takes the listener on a journey through Kembe’s creative yet cluttered mind, allowing him to get all of these thoughts and experiences out there on the table for others to learn from and relate to. Along with this, it seems to allow him to clear his own head and not have to keep everything bottled up anymore, which makes the title that much more relevant to the project. There are so many takeaways from I Was Depressed Until I Made This, but the most important in my opinion is the fact that Kembe X deserves to be recognized globally way more than he already is considering he puts out some of the most relatable and cohesive projects in the industry. If you haven’t listened to this album yet, you don’t know what you’re missing.

10) Chance The Rapper • The Big Day

It would not be far-fetched to say that 2019 might have been one of the best years for Chance. From his various charity events, multiple live television performances, the birth of his second child, his monumental sold-out performance at the United Center, and the release of his official debut album The Big Day. Feeling ever so inspired by his wedding, Chance decided to create an album entirely dedicated to that special day and his special someone—his wife. Chance has always been one to keep fans guessing—not being able to pinpoint exactly what his next move will be, or what his next project will sound like. What we ended up getting was twenty-two tracks of the many feelings, emotions, and vibes of every moment that Chance experienced during HIS big day. Despite the initial reception online which birthed the infamous “I love my wife” meme, Chance was able to remain as dominant as he always has been—delivering one of the best projects to come out of Chicago this year.

Various themes are spread all throughout this project—some of those being the relationship with his brother Taylor Bennett, how having side chicks/dudes is played out, having that “always & forever” love and many more. Chance has always been the artist to pay very close attention to detail and would never release something he did not fully believe in and support whole-heartedly. He secured some mind-blowing features from all genres on this project as well—those among the likes of Shawn Mendes, Ari Lennox, Da Baby, Megan Thee Stallion and many more. The fan favorites of this album would be none other than “Hot Shower” featuring MadeInTYO and Da Baby, and “Handsome” featuring Megan Thee Stallion. Whatever your vibe is, Chance makes sure he has something available for all moods on this album. This was one of the most important projects for Chicago this year, and for Chance’s career as well.

9) Femdot • 94 Camry Music

Chicago native femdot has been building up his name and his brand over the past few years within the city, but it’s easy to say that 2019 was by far his best year to date, especially considering the success of his latest project 94 Camry Music. This project as a whole is based around the car that femdot grew up driving, a 94 Camry, and the songs represent the soundtrack of what that time felt like to him.

After the intro and title track, we got right into “Hot Lunch” that finds femdot displaying his unmatched lyrical excellence, giving punchline after punchline bars that he never seems to run out of. The lone feature on this EP came from the St. Louis legend Smino on the track “Rap City” that finds these two skilled emcees bouncing off of each other, both slicing apart the magnificent production from Ambi Lyrics and showing why they are acclaimed as some of the best in their own respective lanes. The second half of “Late Night Run” is one of the most menacing and banging tracks that I have ever heard, which was a change of pace from the slow and soothing vibe he provided to start the track, but somehow the clash of two sounds meshed flawlessly. Just looking at the title of “Happy Breakup Song” — you can probably assume where that one is heading, as fem gave a beautiful jam-based track all about a breakup he experienced in the past, an ode to the times they spent that ends on a happy and upbeat note. The outro record is arguably the best storytelling record that I have heard in all of 2019: femdot painted a picture that has many twists and turns, it’s an experience in itself and in my opinion, it’s the perfect ending to this tape.

This project was recently named #3 by Fox News when they discussed their top 5 favorite albums of 2019, and for us, it is landing here in the top ten and it even got him a major commercial placement with Toyota for their 2020 Camry. Be expecting to continue to see femdot thrive in 2020, stream 94 Camry Music below and if you enjoy it then keep up with femdot’s movement by following him on Twitter here!

8) Calboy – Wildboy

Calboy is one of the most promising up and comers on this list, and it’s amazing that he’s still technically considered an up and comer with the massive success he’s had within the last year. At only 20 years old, most musicians can’t claim to have chart-topping songs, a record deal, connections with some of the biggest names in the industry, and a double-platinum single, amongst many other achievements.

Calboy already has so many triumphs to show for himself and his debut EP Wildboy is a somewhat culminating project in certain ways. It’s not culminating because his career is over by any means, but it seems to offer us a turning point in his life where he’s going from the streets of Chicago onto bigger and better things, and he’s sharing those messages on every single song on this project. “Envy Me” is without a doubt his biggest hit to date for good reason, and he opens up the record with this cut, which definitely gets it started on the right foot.

On certain tracks like “Love Me”, “Adam & Eve”, and “Nina”, he discusses different struggles he has, not only with the upbringing he persevered through, but the heartbreaks he has sustained and his experiences with drugs, whether they’re about him personally or other people he’s associated with. These songs seem to give him an opportunity to get things off his chest, offering a sort of therapy-like vulnerability that paints a vivid picture for the listener.

His selection of features for Wildboy is beyond impressive, with guest spots from fellow Chicago artists Polo G and Lil Durk, as well as other features like Young Thug, Meek Mill, Yo Gotti, and Moneybagg Yo. The best part about these guests is that they all add so much to the EP without taking any of the shine away from Calboy. My personal favorite song is “Chariot” featuring Meek, Thugger, and Durk because they each have such a different sound typically, but the way that they each lay their verses down works seamlessly with one another. “Caroline” was another favorite of mine, featuring Polo G who’s another fantastic Chicago talent that can understand and appreciate the struggles Calboy has gone through considering he’s faced similar struggles as well. You can also just feel the emotion in Calboy and Polo G’s voices as they sing and rap along, which makes it feel like more of a saga than a song.

Calboy went above and beyond with Wildboy, opening up the door to many opportunities and proving that there are so many different ways that people in Chicago are making music. He doesn’t hold anything back, and that leads to such a raw, emotional project that even if some people might not be able to personally relate with every single story he tells, they can appreciate and respect him that much more for it. The mixture of slower, melody-driven records as well as faster, percussion-forward songs makes the entire project feel fresh for its duration. At around a half-hour long, my only selfish wish is that it lasted longer so I could hear more of these confessionals that Calboy tells so well. You’re already behind the curve if you haven’t listened to Calboy’s debut EP Wilboy, but check it out to make sure you don’t miss out on it anymore.

7) Dreezy – Big Dreez

Dreezy’s 2016 debut, No Hard Feelings, served as a proper introduction to the mainstream music world of one of Chicago’s most versatile voices, and three years later on her sophomore album, she proves she’s only gotten more skilled with time. It seemed like the industry wasn’t sure to do with Dreezy when she first popped onto the mainstream scene in regards to where exactly she fit into the hip-hop or R&B spheres, and the reason behind this initial confusion probably has to do with the fact that no one’s ever done it quite like her. On Big Dreez and in the context of 2019, where genre lines have only gotten more blurred and mixed, Dreezy hones in on her perplexity and wields it as a weapon to forge her own path.

Over these 10 tracks, Dreezy’s completely in her own lane, unbothered by how anyone else around her is moving. At the center of the project is one of the most attention-grabbing voices in the game right now bringing cutthroat conviction behind everything she says on the mic. She continues to command the mic even on the album’s softer moments, combining auto-tuned bliss with fluid flows in a flurry that only she could contain. She takes listeners to the extremes of her sound on this project, from the ruthless opening track “Chicken Noodle Soup” to the full-on R&B duet with Jeremih on “Ecstasy”. All the way through, Dreezy reminds anyone who might’ve fallen asleep on her of her prowess. The depth of her talent allows her not just to embody a technically-skilled emcee but also an artist with an ear for addictive, lullaby-like melodies. It’s a juxtaposition that not many artists could reconcile without it sounding like a mess, but Dreezy does it with finesse on Big Dreez.

6) G Herbo • Still Swervin

There are a few artists that simply need to be included on this list otherwise there would be absolutely no credibility, and G Herbo is without a doubt one of them. Still Swervin, the follow up to the rapper’s 2018 offering Swervo, shines a new light on the Chicago sensation in certain cuts while allowing him to return to his roots on others.

Although it may not have peaked as high on the charts as his previous works, that shouldn’t have any sway in anyone’s opinion of this album. His passion for telling his stories in their true form and never sugarcoating them is a feat in itself that most rappers have trouble sticking to, but Herb never quivers when it comes to this. Even though he’s made a better life for himself, his recollections will never disappear and they’re not only incredible to listen to, but the visuals he verbally paints are enough to make you feel like you’re there. When it came to Swervo, it seemed as if G Herbo was thankful for the spot he worked so hard to get to, so it was kind of a project dedicated to his gratitude for his situation. With Still Swervin, he seems comfortable with the fame and success that he’s possessed for a few years now, so he makes an effort to create a mixture of old tales from his neighborhood as well as new experiences his achievements have brought him. One of the album’s front-end tracks, “Scratchy & Itchy”, has to be one of my favorites early on. Rapping over some sort of soul sample, he seems to have more of a sense of calmness as he retells experiences from years past, but the details he goes into are immense. My personal favorite version of Herb is when he goes all out, ferociously spitting lyrics that seemingly slap you across the face. There’s a surplus of these on the album, but some of the songs I tend to enjoy more than others include “Up It”, “Yerk 30”, and “Boww”.

The features included also don’t play around in the slightest. Huge names like Gunna and fellow Chicagoan Juice WRLD bring the heat on their respective tracks, while smaller named artists Lil 40 and Pretty Savage take full advantage of their placements and make their names known. Overall, I’d be lying if I said Still Swervin is my favorite project G Herbo has ever dropped, but it’s amongst a crowd of other mixtapes and albums that are pretty much flawless, so they’re going to be difficult to top. If there’s one major takeaway from this album, it should be the fact that no matter how experimental Herb might get with his production, flows, or lyrics, he’s always going to be one of the quickest, most aggressive, and talented drill artists to ever hold a mic period.


5) Tobi Lou • Live On Ice

Tobi Lou’s “moment” was inevitable, and this year with the release of Live On Ice, it’s inarguable that his moment has arrived both in terms of the artist’s growing level of hype and his growing mastery of his own artistry. He’s refined his melodic, carefree style of rap over the years, and his melodies have only grown more infectious and his sense of humor more cunning. With this sonic base already established, Live On Ice presents a 21-track exercise in stylistic dexterity tempered with consistency. It’s a longer tracklist than most artists would be willing to put out in 2019, but the project’s depth ultimately swings in Tobi’s favor as he seamlessly weaves in and out of each song in a way that makes it nearly impossible to hit skip even once.

An ongoing theme that Live on Ice exudes is the idea of finding joy in the darkest chapters. This theme manifests literally on “I Was Sad Last Night I’m OK Now”, executed in true tobi lou fashion where nothing is ever too serious for a laugh or a smile. He evokes this emotional juxtaposition of light in darkness throughout the album in the form of imaginative metaphors that bring comic relief to sincere confrontations with feelings of self-doubt and negative self-talk. tobi dances through it all with a tone of genuine optimism that’s infectious for a listener in the best way possible. Not to mention the constant bounce that gets carried across the album’s production thanks to work from producers like Matteo Woods, Facer, Noah Breakfast, and tobi himself among others.

Running with such a consistent style for over an hour on one project could easily get repetitive from a listener standpoint, but tobi lou dodges sounding played out by knowing just when to switch things up to keep a listener intrigued. Along the way, he reveals the most cohesive culmination of who he represents as an artist so far. Live On Ice feels like a celebratory album by an artist who truly found his bag and is always ready to reconfigure his approach for whatever’s next.

4) Lil Durk • Love Songs 4 The Streets 2

Lil Durk is in a lane of his own. As most fans know, he first entered the music scene earlier this decade through drill anthems that he created in the streets of Chicago with his friends. He saw how massive the rap sub-genre was going to grow to be, so he capitalized on that and watched his fame skyrocket. Fast forward a few years later, being the smart and talented artist that he is, Durk noticed how drill music was beginning to become too repetitive, and fewer and fewer artists making that kind of rap were rising to stardom. He recognized this trend and actually decided to differentiate himself, setting himself apart from the crowd. He did this by getting more melodic within his songs, almost turning into a cross between his original sound and an updated version of R&B. He never forgot his roots, however, and Love Songs 4 the Streets 2 reminds us of that.

With a run time of about 40 minutes, this 16-song album gives us a little bit of everything that we know and love about the Chicago star. With pain-filled testimonials like the opener “RN4L”, as well as “Locked Up” and “Rebellious”, Lil Durk wears his heart on his sleeve, confessing how some of the things that happened in his past affected him, and he won’t be quick to forget them. He also looks back to his old self, producing some extremely hard-hitting classic drill hits like “Like That”, ‘Green Light”, and “Weirdo Hoes”. Durk also brings this timeless genre to some of his features which added just enough to the album without actually interrupting his own spotlight. This can be found in “Die Slow” which features 21 Savage, who merges his somewhat haunting persona with the drill aesthetic that Durk brings to the table. On “Extravagant”, Nicki Minaj provides a very raunchy and explicitly sexual verse that seems to just be shoved right into the middle of the project to be honest. On another note, Meek Mill brings his hyper side to “Bougie”, which is a song that I would think was his rather than Durk’s considering all signs point to Meek’s musical style rather than Durk’s, but the Chicago artist shows out and impressed me with his verses, nonetheless.

Love Songs 4 the Streets 2 is just that, an ode to the streets and community as a whole that raised him. You can tell that there’s definitely some good he’s been exposed to in his city, even in the midst of all the bad that people always hear about. The journey he takes us on from the first to the last song offers many different lessons, stories, and perspectives. Even with a few small miscues throughout, this album shows us who Lil Durk is plain and simple. He’s one of the artists that has helped put the Chicago music scene on the map and that’s something that always needs to be remembered because it’s one thing that no one can ever take away from him.

3) Polo G • Die A Legend

Polo G is someone who many people might consider strictly a drill artist and end the discussion there, but listening to Die A Legend should be able to completely change their minds. Throughout this project, Polo G takes the reigns and goes from a local icon to a nationally-recognized star. One of the reasons for this is the absolutely massive success that his single “Pop Out” featuring Lil Tjay became, playing on radio stations, in clubs, and blasting through car speakers across the country. It got so popular, in fact, that Lil Baby and Gunna had to jump on a remix to round out the album. There’s no denying the success of this track, but it definitely shouldn’t overshadow the greatness that the rest of the project demonstrates.

This greatness starts out with “Lost Files”, which is one of the heaviest drill cuts off the project. It sets the tone of the album, describing in vast detail his experiences in the streets of Chicago and the inspirations for wanting to make a better life for himself and the people around him. This seamlessly leads right into “Dyin Breed”, where Polo G recounts some of the hardest losses he’s encountered throughout his life, including both friends and family members. This is a ruthless track that allows him to share the awful fates of those he has been around for his whole life. “Through Da Storm” comes up next, telling a tale on the opposite end of the spectrum, beginning with a soundbite from his sister telling him how proud she is that he has made something of himself and has reached the level of success that neither of them ever dreamed of. On this song, Polo humbly appreciates what his hard work has given him and never takes it for granted. The topics he discusses in the first few songs on this album lay a foundation for the rest of the project. Some reoccurring themes such as his struggles, success, family, and never stopping his grind pop up all over.

I want to compare Polo G to a mixture of drill legends, but that just isn’t what he is. He has such a versatile skill set that allows him to expertly rap as well as sing, but that’s not all. His tales of despair are special because you can hear the emotion in his voice as he relives those very moments in the booth. His stories of success are unlike anyone else’s because he isn’t gloating in the slightest, but rather appreciating that he can not only live a safer life than what was originally meant for him but offer a better life all around for his daughter and the rest of his family. Polo G possesses a talent that is unmatched from anyone in music today, and Die A Legend is yet another example of why this is the case. If you haven’t heard the album yet, put it at the top of your list because the stories he tells are vivid, real, and told better than almost anyone he might get compared to.

2) Lucki • Freewave 3 & Days B4 III

Lucki’s ability to reinvent himself with every release while still trailblazing is a testament to his creativity. Most established artists at the tail end of their career would dream for a catalog as impressive as Lucki’s at the mere age of twenty-three. The first of Lucki’s 2019 projects, Freewave 3, continues his vision of evolving and creating a dynasty that will outlast us all. It contains ambitious experimentation, consuming the listener deeper and deeper into his world with a varied soundscape that changes depending on whether he’s running from loss, heartbreak, or addiction. Lucki addresses his inability to hold onto meaningful relationships due to his vices, and in turn, questions and evaluates his place through terrifyingly honest lyricism. Through his comfort with being uncomfortable, he’s able to create a transparent experience for the listener.

Lucki puts a different raw feeling into every track on Freewave 3, backed by immersive, textured production that gives listeners a taste of what Lucki is feeling before moving onto the next short story. Lucki’s emotive flow and catchy refrain on the song of the year contender, “More Than Ever,” hits home and grasps the listener, despite the ferociousness of the show-stopping instrumental. He shows us his vulnerable side on the shimmery, minimally-percussive “Peach Dream”, and drops us in the trenches for “All In,” with a beat (produced by Earl Sweatshirt) that features an obscure vocal sample no other rapper could do justice to.

Lucki found it fit to celebrate once more in 2019 with Days B4 III, a body of work that proves his consistency isn’t going anywhere. Although murky throughout, Lucki is a bit more grounded on this project compared to Freewave 3, coping with and accepting the way things are, and understanding what’s really important to him. While Freewave 3 saw Lucki questioning his place (“used to think they was gang, now I’m like who is you?”), Days B4 III sees him controlling what he can, rapping “stick to myself ‘cause these n***as be wildin’” over a steady drum pattern and uplifting lead melody on “Me Myself & I”. Following this, he accepts the beauty of the way things fall into place on the enthralling, ever-so-focused “4 The Betta”. Lucki is maturing as an artist and a human being. He’s a legend in the making, but we knew that already.

1) Juice WRLD • Death Race For Love

When you think about the fact that Juice WRLD was able to accomplish so many different things in just under two years of making music, it almost doesn’t make sense. It seems as if it would be IMPOSSIBLE for anyone to make that much of an impact on the world in such a short amount of time, but he did thatIt’s unbelievable how fast Juice WLRD rose to stardom while staying as true to himself, as consistent, and as entertaining as he was. 

It’s clear from his earliest work that Juice wore his heart on his sleeve in his music, and that sentiment resonates with even more vulnerability across these twenty-two songs. The angst at the core of his biggest hits still exists on Death Race For Love at the album’s most desperate moments, but it’s met with newfound levels of maturity and numbness, symptomatic of Juice’s lightspeed rise to fame. He wrestles with new demons on this project, conquering some and succumbing to others, and he lays it all out on the record in a way that anyone could relate to in their own experiences. His ability to connect with a listener in his lyrics only gets amplified by his signature ear for punk-influenced melodies that mimic these unabashed emotions. Juice also finds an intentional balance of his talent on Death Race For Love, allowing both his vocal range and textbook rap abilities to get equal amounts of shine and materialize on standout tracks like “Empty”, “Hear Me Calling”, and “Robbery”. 

Although Juice WRLD had already reached massive superstardom when Death Race For Love released earlier this year, there’s something within his music that’s always humanized him. This is crucial because it allowed listeners to relate to him while idolizing him at the same time, which is an odd but very lucid relationship that fans might share with the rapper. The impact that Juice WRLD had on his fanbase, the music community, the city of Chicago and the whole world truly cannot be put into words, but one thing is for certain: his legacy will live forever and he will continue to inspire the masses for years and years to come.

Cover art by Grif

Words by Elliot Montanez, Mike Del Rosario, Seamus Fay, Danny A, Jarred Howard