Throughout the 2010s, Chicago positioned itself as an undeniable force in the rap game, for the best and worst reasons. As a people, Black Chicago has always been relevant: peep our esteemed literary culture that progressed through the works of Eve Ewing, Charlene Carruthers, Nate Marshall and the entirety of Young Chicago Authors. We saw sports under the reign of former Chicago Bulls star and Englewood native Derrick Rose. There were television shows like The Chi and South Side and films like Spike Lee’s polarizing Chi-Raq. Political and radical activism was predominantly led by Black, Brown and queer women. The 2012 re-election of President Barack Obama. Our slang — like “packs,” “thot/thotiana” and “on foe ‘em” — made its way across many hip hop records. Chicago’s notorious gang culture made countless headlines across national news for the scores of lives lost every year. And a highly diverse music scene that remained true to the Blackest corners of the second city.
Life in Chicago got more complicated at the dawn of the 2010s. With the destructive and divisive reign of former Mayor Rahm Emanuel, alongside a gun violence epidemic and the killings of unarmed Black people by Chicago police, the city’s sound shifted. Chicago music became the main outlet of expression for joy, pain, trauma, celebration, community, war and glory. Picking up the baton from ground-breaking 2000s icons such as Kanye West, Lupe Fiasco, The Cool Kids, L.E.P. Bogus Boys and Bump J — with a little added flavor from the likes of Atlanta’s Gucci Mane and Waka Flocka — a new, younger and bolder generation of Chicago artists rose in stardom and influence.
Early 2010s rappers such as Chief Keef, Montana of 300, King Louie, Lil Durk, Hypno Carlito, Katie Got Bandz, Chance the Rapper, Young Pappy, L’A Capone, P. Rico, RONDONUMBANINE, Lil Jay, Lil Bibby, Vic Mensa, G Herbo and many others were among the first in Chicago to fully harness the power of the internet and social media. Without the restrictive structure of the music industry, where past teen artists such as Mobb Deep, Lil Wayne and Kriss Kross were molded and guided differently, this new wave of Chicago artists fully dictated their own careers.
Through creative, gritty and in-your-face music videos that highlighted street and youth culture on Chicago’s South and West sides — often directed by DGainz, A Zae Production, or Cole Bennett — hip-hop fans across the country caught a glimpse inside the city that became infamous for its homicide rate. It helped that video journalists like the late Zack Stoner of ZackTV, writers like David Drake, and local blogs like Kollege Kidd and Fake Shore Drive brought exposure and cultural context to the entirety of Chicago hip hop through in-depth interviews, extensive coverage and consistent premieres when mainstream outlets wouldn’t give these artists the time of day.
Arguably, the same can be said about influential YouTuber and controversial Everyday Struggle host DJ Akademics, who also brought national exposure to most of the drill and drill-adjacent rappers disregarded by legacy music media. But, unfortunately, DJ Akademics did so through exploiting Black Chicago’s ugliest reality through his “War In Chiraq” channel.
The music, visuals, and viral marketing greatly influenced mainstream hip hop in ways that are being emulated today by most of the major record labels and rappers such as Bobby Shumurda, NBA Youngboy, YBN Nahmir, Cordae, and Almighty Jay as a collective, Sada Baby, Cardi B, OMB Peezy, Lil Pump, Snap Dogg, Tee Grizzley, Fetty Wap, Young M.A., A Boogie, 21 Savage, Lil Uzi Vert, Playboi Carti and the incarcerated (for now) Tekashi 69, to name a few. Whereas viral, yet controversial videos like Chief Keef’s original “Don’t Like” were deleted from YouTube at one point, scores of preceding videos with gang-related, hyper-violent content, nationally and locally, have since been allowed to thrive there.
Unfortunately, being the first of their kind came with setbacks for most Chicago rappers. Their music and celebrity popped before the rise of streaming giants such as Spotify, Apple Music and Tidal. Inadvertently, drill classics like Sosa’s Finally Rich and songs like G Herbo and Lil Bibby’s “Kill Shit,” Katie Got Bandz’s “Pop Out,” and Lil Reese’s “Traffic,” among many more, missed out on climbing the Billboard charts and possibly profiting even more from both YouTube and streaming platforms like today’s artists. Thankfully, Chicago artists caught up by 2014, which led to Chance the Rapper’s come-up as the biggest winner in the streaming war. He was the first independent artist, of any genre, to release a streaming-only album exclusively with Apple Music and the first to win a Grammy for it.
Most of the albums, singles and visuals from the early drill era weren’t mainstream friendly at the time. Cult hits like “Everyday”, “Killa”, “Play For Keeps” and “L’s Anthem” went viral on YouTube and became successful songs, but didn’t get much radio play outside of late-night mix shows on urban stations upon their release due to their gang-related content. However, the Glory Boyz would have the upper hand with the Kanye backed “Don’t Like (remix)” and “Love Sosa” climbing the Billboard charts, finding its way into regular rotation on hip hop stations beyond Chicago. Lil Reese and Lil Durk would each sign to Def Jam while Chief Keef famously signed to Interscope. Outside of GBE, King Louie would find his way to Epic and Lil Bibby signed with RCA.
Until very recently with JuiceWRLD, Calboy, Polo G and FBG Duck rising to national fame, these five would be the sole and most popular artists connected to drill who had record deals and songs in regular rotation. Chief Keef would be the first RIAA certified artists with a gold plaque for Finally Rich and two platinum plaques for “Don’t Like” and “Love Sosa.” Lil Durk followed Keef much later, earning three gold plaques for his radio-friendly tracks “Like Me,” “My Beyoncé,” and “Homebody.” Longtime GBE/OTF (Only The Family) affiliate Hypno Carlito would be first and only drill artist nominated for an Academy Award for writing Nick Cannon’s “Pray 4 My City” from the Chi-Raq soundtrack while King Louie was the first to be nominated for a Grammy after he penned Kanye’s “New Slaves.”
While drill was bubbling like molten lava, another side of Chicago’s music scene started drawing from the spoken-word, blues, and underground hip-hop tradition mixed with unorthodox and colorful creativity. That’s where Chance the Rapper, Ric Wilson, Vic Mensa, Jean Deaux, Smino, Saba, Noname, Chris Crack, Joey Purp, Kami, and Mick Jenkins found their niches. Each represented the radically diverse identities of a young, rebellious and hyperlocal counterculture — however, out of this particular class of hip hop artists from the Chi, only Chance the Rapper really ever found a way to get his raps on not just urban radio, but on mainstream top 40s pop radio as well. With the exception of Vic Mensa, who also rubbed shoulders with Yeezy and signed with Roc Nation, everyone else from this class intentionally steered away from being mainstream in lieu of building their own cult followings. Each of them did this through high quality and critically lauded projects like Noname’s Telefone and Room 25, Mick Jenkins’s The Healing Component, Chris Crack’s Being Woke Ain’t Fun, Smino’s blkswn, Vic Mensa’s INNANETAPE, and Joey Purp’s iiiDrops, among many others. This group developed a deep connection with their fans through social media and touring music festivals and intimate venues across the US and Europe.
It was the diversity, quality, originality, controversy and the magnetic appeal of Black Chicago culture that attracted audiences to our 2010s sound rather than the one-rapper-at-a-time mentality that was highly prevalent in the 1990s during the rise of Twista, Da Brat, and Common.
So, as we near the end of the decade, and all of the “best rapper” lists start to circulate across social media, we figured we’d make the definitive list of the top 10 influential Chicago rappers of the 2010s decade.
These 10 artists each represent a unique and connected narrative of life in Chicago. Their impact also lingers within the city limits in Chicago rap, within national and mainstream hip hop, and across the global music scenes throughout the world.
During drill’s breakout between 2011 and 2014, women such as Shady, Katie Got Bandz, Sasha Go Hard and Dreezy were all proving that the lady hittas can be just as fierce, lyrical, charismatic and exciting as the fellas. When Tink became part of that special class of women rappers, she was an anomaly at the time because to this day, there have been very few artists, male or female, who can rap and sing at an equally high level since Lauryn Hill.
Versatility was, and still, is Tink’s greatest strength as she simultaneously provided the soundtrack for the lady drillers with 2012’s Blunts and Ballads and 2013’s Boss Up, while offering her sensual, vulnerable side with the Winter’s Diary series beginning in 2012 and 2019’s Voicemails. She’s significant to this decade of Chicago hip hop, not just for her high level of versatility, but her music added a neglected narrative of the lives and stories of Black girls and young women in Chicago. Arguably, her music led to the rise of female Chicago artists like CupcakKe, Ann Marie and Kari Faux. Considering how she’s finally bouncing back after being in limbo after signing a deal with Timbaland in 2015, don’t be surprised if Tink begins to dominate throughout the forthcoming 2020s.
Historically, the South Side of Chicago has been the most consistently dominant across the country thanks to Shawnna, Common, Kanye West, No ID and Chief Keef. Despite the West Side planting its flag throughout the 1990s and 2000s with Twista, Crucial Conflict, Da Brat, and Lupe Fiasco, for a while the West Side’s hip hop scene was relegated in the shadows as its veterans were removing themselves from the spotlight.
All of this changed in 2012, when the Young Chicago Authors alum Saba dropped his debut project, GETCOMFORTable, and his back-to-back collaborations with Mick Jenkins on “Heaux” and more famously, Chance the Rapper on “Everybody’s Something” from Acid Rap. Things really started to catapult for the Austin native after he released his critically acclaimed Bucket List Project in 2015. He earned a national reputation for being Chicago’s premiere spitter, with his intricate and poetic storytelling and gripping narratives of his personal story. He then solidified his place as one of hip hop’s top-tier artists when he dropped his somber and compelling follow up Care For Me, which was dedicated to his late cousin John Walt, who was tragically murdered in 2017 at a Metra train station.
Saba and his PIVOT Gang crew have a unique roster that’s steadily blossoming across hip hop, literature and local humanitarianism. Out of the PIVOT Gang family, his brother Joseph Chilliams and high school friend MFn Melo are becoming critically acclaimed mainstays of their own, with projects like Henry Church and Melodramatics, respectively.
Friends and PIVOT Gang affiliates author Britteney “Black Rose” Kapri and poet Raych Jackson are earning acclaim as well for their works, 2018’s “Black Queen Hoe” and 2019’s “Even the Saints Audition,” respectively. And when it comes to giving back to their community, they do it all in the memory of John Walt through the John Walt Foundation, which offers scholarships and mentorship opportunities to young aspiring Chicago artists, along with the annual celebration of his life, John Walt Day, happening this year on Nov. 29th.
Between drill and the eclectic spoken-word hip hop that dominated the decade, there came a unique outlier in Valee. The walking, breathing human vibe finessed his way on the national scene after dropping his VTM mixtape alongside CHASETHEMONEY, followed by a string of one and two-minute visuals like “I Got Whatever,” “Shell,” and his joint effort with Z-Money, “Two 16s,” each garnering millions of views on YouTube. Eventually, this would lead him to a deal with Kanye’s G.O.O.D. Music and releasing two EPs — 2018’s G.O.O.D. Job You Found Me and 2019’s Running Rich.
Despite his short, but growing, time on the national scene, Valee rapidly influenced mainstream hip hop with his smooth, quiet and metronomic flow, one of the biggest draws to his mesmerizing hooks and verses. And like much of Chicago music, his style was ripped off by rappers like Tekashi 69 and Nicki Minaj on “FEFE,” Lil Pump on “Gucci Gang” and SmokePurpp on “Nephew,” the latter being notorious for blatantly sounding like the Jerimih-assisted “Womp Womp.” Thankfully, this hasn’t stopped Valee, as he still has a strong career after dropping 2019’s Running Rich and hopping on songs with Vic Mensa, YG, Smino, JuiceWRLD, Phor, Hypno Carlito, Calboy, 808 Mafia and Matt Ox, and the list keeps growing.
As drill started becoming more diverse with different styles, melodies and themes midway through the 2010s, a unique oddity rose from the blood and gunsmoke with an insane amount of flash, dance moves, and charisma. Enter South Side’s own Famous Dex, who brought a lighter and more fun air to Chicago hip hop after breaking out in 2015 with his debut mixtape, Never Seen It Coming, followed by Dexter’s Laboratory that same year.
Where many of his peers like Lil Jay, Chief Keef, P. Rico and FBG Duck carried a darker, violent sound and energy, Dex created a complete contrast to drill with his own colorful, yet edgy style. He was known for his colorful dreads and fluid, non-stop dance moves accompanying his fun, catchy ad-libs like “WOAH,” “Wait!” and “DEXTERRRRRR” — all with bouncy cadences and flow. He quickly became a draw for fans across the country with classic songs such as “Drip From My Walk,” “Hoes Mad” and “Pick It Up,” which featured A$AP Rocky. His roots clearly come directly from drill, as some of his visuals and lyrics contain its grittier, street-savvy side.
Thankfully, the appeal of his music and videos did not depend on gun or gang talk to carry him throughout the end of the decade. He became a platinum-selling artist with “Pick It Up” and his biggest mainstream hit, “Japan.” And it helped that Dex eventually signed to Rich Tha Kid’s label, Rich Forever Music, which helped his music and celebrity grow even more.
It’s hard to accurately gauge Dex’s immediate influence because his career took a devastating hit after two incidents: being caught on a hotel security camera assaulting his girlfriend in 2018 and a well-documented drug addiction that led to him notoriously nodding off while live on Instagram. He has since claimed to quit drugs for good. However, his classic singles still have fans going insane at concerts and parties. So there’s a chance that his legacy could continue even brighter into the 2020s.
While drill music led Chicago’s sound for most of the decade, other musicians and poets — particularly those from the Young Chicago Authors camp — ushered in a new wave of soulful, joyous, rebellious, experiential and eclectic tunes, providing a much-needed balance in the city. Being a part of the generation of rappers, writers, activists, artists, animators, fashion designers and entrepreneurs directly influenced by pre-MAGA Kanye’s inclusive, pro-black content, spoken-word lyricism paired with compelling and revealing songwriting, highly colorful and animated art and fashion direction, along with Lupe Fiasco and The Cool Kids, it only made sense that a rapper like Chancelor Bennett would be the one to carry the baton.
A lot can be said about Chance’s constantly evolving style, content and business moves. 10 Day introduced us to his unorthodox, yet relatable, hyperlocal content and deep, layered musicality and lyricism, while Acid Rap pushed this further by finding a perfect balance between hazy, eclectic, drug-heavy content and soulful, uplifting melodies and lyrics backed by gospel-inspired sounds.
The groundbreaking Coloring Book saw Chance the Rapper tone down the grittier aspects of his music and sonically move forward with melodies, choirs and live instruments by long-time collaborators Nico Segal and The Social Experiment. His themes and lyrics also became more personal as they centered more on his spirituality, family, his personal life and the nostalgia of growing up in Black Chicago as a shorty. The Big Day, on the other hand, saw him push even further on themes of spirituality, marriage and family while still maintaining the zaniness we appreciated him for in the first place with (controversial) songs like “Hot Shower.”
Songs like “Summer Friends,” “Same Drugs” and “No Problems” from Coloring Book embody the stolen joy of an abused and terrorized Black Chicago, and all of its care-free love. And each of these tracks led to him being the first artist to win a Grammy from a streaming-only album.
With his fame, glory and riches, Chance is becoming one of Chicago’s most important humanitarians and activists. He continued to make a difference throughout the 2010s when he donated $2.2 million to Chicago Public Schools, joined local activists across the city to protest former Mayor Rahm Emanuel’s proposed $95 million police academy, co-founded SocialWorks for high school kids to perform open mic raps and poetry, endorsed and supported Amara Eniya’s 2019 mayoral campaign, bought the Chicagoist news website and met with former Gov. Bruce Rauner to continue his fight for public education.
Chief Keef and GBE made drill a national phenomenon. But drill’s origins began with the late Pac Man, a.k.a. Larro, the man who not only coined the genre’s name but also made waves with cult hits such as “Dro Style.” Unfortunately, his career was cut short when he was gunned down in 2010. His influence, though, gave rise to close affiliate King Louie, who would be one of the first rappers from the Dro City lineage to take off nationally.
Over the decade, King Louie steadily made his mark in music through classic tapes like 2012’s Showtime, 2012’s Drilluminati series and 2015’s Tony, which featured his cathartic anthem, “To Live and Die in Chicago.” He even made a huge mark on pop culture, as he’s credited as the creator of Chicago’s maligned nickname Chiraq. While other artists who came after him — like Chief Keef, Lil Durk, G-Herbo and JuiceWRLD — may have exceeded him nationally, it’s likely that had it not been for King Louie, much of Chicago’s hip-hop landscape, or even the larger trap music movement, wouldn’t be what it is today. And you can hear the distinct influence in the flow of Young M.A.’s “Big Drip.”
Throughout the decade, Chatham’s own DJ L has been Chicago’s best-kept secret when it comes to beats. Despite his low-key presence, his dark and frantic production style managed to spread from Chicago across the pond in the United Kingdom, which directly influenced U.K. drill. And it all kicked off with Lil Bibby and G Herbo’s viral breakout duet “Kill Shit.”
His influence can be heard in rolling drums and rapid-fire pacing inspired by footwork/juke music, and his time as a drummer with the South Shore Drill Team, along with the menacing and at times, soulful soundscapes that made projects like Lil Bibby’s Free Crack and G-Herbo’s The Pistol P Project and Ballin Like I’m Kobe the street classics that they are. In fact, he helped Herb and Bibby lay down the musical foundation that would make them the artists they are today.
As a result, the two 79th and Essex spitters pushed drill forward by adding much-needed context to the rampant violence in Black Chicago. They also proved that drill rappers can be lyrical and make thoughtful and conceptual songs that gave a balance to the sub-genre in its entirety, with tracks like Lil Bibby’s “Water” and Herb’s “Bottom of the Bottom” and “Red Snow.” The lineage continues with Bibby and his brother G-Money’s Grade A Productions, which brought the world Chicago’s fastest-rising superstar, JuiceWRLD.
He might not have as many gold or platinum plaques as his contemporary Young Chop, but DJ L’s musical influence penetrated Chicago and national hip hop. His sound can be heard in songs like Nicki Minaj’s “Chiraq” and Meek Mill’s “Chiraq (remix)”, JuiceWRLD’s “Maze”, Drake, Jay-Z, and Kanye’s “Pop Style” collaboration and the comedian Big Shaq’s viral sensation, “Mans Not Hot.” Earlier in 2019, DJ L landed another viral hit with Lil Uzi Vert’s “Free Uzi” and as mentioned before, his sound was one of the driving inspiration behind UK drill.
After breaking barriers, shattering glass ceilings and making classics during the 2000s, the 2010s is where we saw Yeezy at his highest, lowest, most shocking and most ambitious when it came to music, art direction and fashion. He gave us his 2010 masterpiece, My Beautiful Dark Twisted Fantasy, followed by the monumental joint album with Jay Z, Watch the Throne and the polarizing Yeezus, The Life of Pablo, along with Ye, and his string of seven-track albums by Nas, Pusha T, Teyana Taylor and his collaboration with Kid Cudi.
Even as West became a full-fledged superstar, he still carried Chicago with him. Regardless of how we feel about his ongoing support of President Donald Trump, or how many of us are skeptical of the motivations behind his confessional rants and religious kick, you can’t deny that his 2010s run legitimized Chicago music around the world.
After helping to turn Chief Keef’s “Don’t Like” into a mainstream smash with a remix featuring himself, Pusha T and Jadakiss, Kanye gave Keef, Young Chop and King Louie an alley oop on Yeezus where King Louie received his first Grammy nomination for “New Slaves.” West then co-signed both Vic Mensa (“Wolves”) and Chance the Rapper (“Ultralight Beam”) on The Life of Pablo, signed Valee to G.O.O.D. Music and donated $73,540 to grassroots activist Amara Enyia’s 2019 mayoral campaign in Chicago. Whether you feel that his actions were genuine or self-serving, ultimately, Chicago hip hop benefited from Yeezy’s signal boosting.
Most of the women who arrived during drill music’s apex are severely underrated such as Dreezy, Shady, Tink and Sasha Go Hard. And while all of them are uniquely talented, there weren’t many who drew heads and ears like the first lady of drill, Katie Got Bandz.
By her account, she was one of the first young, pistol-toting female rappers from Chicago who made a name for herself. The Low End’s lady hitta stood out for her aggressive delivery and persona paired with loud and insanely catchy ad-libs like “BOW BOW” and “KATIEEEE.” Although stylistically, Katie was the least thorough lyricist compared to Sasha, Tink, and Dreezy, she made up for it through her brash, explosive approach on songs like “Pop Out,” “Inaugural Fuck You’s,” “Make Me Rich.” She is arguably one of the most significant women to arrive because she filled a huge void for young women who were part of, or victim to the rampant gang and gun violence. Victims such as the late 17-year-old Gakirah Barnes weren’t being represented in the drill movement.
While Katie Got Bandz did not reach the same heights as her male counterparts, due to creative differences with record labels and fighting depression, she made her mark on hip hop by paving the way for a lot of the women you see in today’s renaissance of female rappers who carry that young, ratchet and aggressive energy: Cardi B, Molly Brazy, Queen Key, City Girls and Asian Da Brat f.k.a. Asian Doll, just to name a few.
Let’s be real. Chief Keef, the late Fredo Santana, Lil Durk, Young Chop, Lil Reese and the rest of the GloGang extended family are the young godfathers of modern Chicago rap. Additionally, they’re the originators of this generation of rappers who blew up on YouTube and Soundcloud, a defiant move away from the old guard of local industry vets and major record labels. They followed in the footsteps of Soulja Boy, who laid the original blueprint for going viral on the Internet with “Crank Dat.” But the GloGang movement picked up where Big Soulja left off. Through a combination of gritty music videos, and hyper-real content that eventually became the scapegoat for the all-too-real gang violence that made local and national headlines, the timing of GloGang’s individual and collective success was serendipitous.
Their contributions are worthy of a separate in-depth article. While Chief Keef, his cousin, the late Fredo Santana, and Lil Reese popularized their distinct flows, cadences, and intimidating imagery from their dreads, slang and tattoos, Young Chop popularized the haunting, brooding, 808 and key-heavy production that influenced modern trap’s sound.
Lil Durk, who was influenced by Bone Thugs & Harmony and Future, broke through with a combination of aggressive street raps combined with auto-tuned melodies. He heavily improved on this combination throughout the decade by refining his voice, improving his lyricism and adding mature and introspective content. This, in turn, influenced a generation of young, melodic hip hop crooners across the country.
Essentially, the impact of the Glory Boyz is twofold: one, they helped magnify the realities of gun violence, extreme poverty and drug addiction across Black Chicago (which some could argue was more of a glorification rather than intentional awareness). Two, they showed a new crop of rappers that, with a serious DIY attitude, they too could spark their own careers without the help of a record company or a radio station. Most importantly, they influenced a plethora of today’s hip-hop stars, including NBA Youngboy, Bobby Shumurda, A Boogie Wit Da Hoodie, Tay-K and Tekashi 99. And on our own home turf, they paved the way for newcomers like Calboy, King Von and Polo G, just to name a few.
Chicago’s impact on the culture is what makes our city a permanent fixture in the minds and ears of mainstream America. In the words of legendary DJ Pharris, “It’s Chicago, nigga!”
