Rappers on the Rise

The dominant styles of rap coming out of Chicago—drill, bop, and a harder-to-categorize kind we’ll call alternative—have been associated primarily with Chief Keef, Lil Kemo, and Chance the Rapper, respectively. These three teenagers (OK, Chance is 21) are the unofficial leaders of a crew of up-and-comers, many of whom grew up in the same neighborhoods and frequently collaborate on the same projects. Here are the key people to watch.


This Englewood-born minimalist gangsta rap goes heavy on the synth and snare, with lyrics often taking a back seat.

Chief Keef

With an Interscope deal rumored to be worth $6 million, Keith Cozart is Englewood’s breakout star, with whom all young drillers are compared.

Age: 19
Twitter: @chiefkeef
Trademark: Mush-mouthed delivery paired with sinister beats
Recommended track: “I Don’t Like”

Lil Durk

Both Keef and Lil Durk are part of the crew Glory Boyz Entertainment.

Age: 21
Twitter: @lildurk_
Big break: A 2013 deal with Def Jam Records. Look for his debut album, Remember My Name, due out this year.
Recommended track: “Right Here”


Lil Herb

Frequent collaborators Lil Herb and Lil Bibby have a joint mix tape, Heir Apparents.

Age: 18
Twitter: @LilHerbie_Ebk
Trademark: Dextrous flow and introspective lyrics
Big break: A cameo on Nikki Minaj’s controversial single “Chiraq”
Recommended track: “Mamma I’m Sorry”

Lil Bibby

Age: 19
Twitter: @LilBibby_
Big break: A cosign from Canadian rapper Drake
Recommended track: “Tired of Talkin’ ”


Drill’s lighter, more upbeat West Side cousin sounds like video game accompaniment (thanks, Auto-Tune)—perfect for the fluid, rapid style of dance that shares its name.

Lil Kemo

Though the face of bop doesn’t rap much, Travon Biggs is a YouTube sensation, thanks to his buoyant dance videos.

Age: 18
Trademark: A dance form like the Charlie Brown, with an emphasis on the knees and elbows
Watch this: “Dlow and Kemo”


Besties Lil Kemo and Dlow taught Steve Harvey how to bop on his WB talk show

Age: 18
Twitter: @bopkingdlow
Trademark: The line dance Dlow Shuffle (Cupid shuffle meets bop)
Big break: A record deal with Atlantic Records in March
Recommended track: “Dlow Shuffle”

Lil Ceno and Lil Trav
(Sicko Mobb)

Ages: 21 and 19
Twitter: @sickoworldfp
Big break: Signed to Sony/ATV last December
Recommended track: “Fiesta”

Breezy Montana

Age: 24
Twitter: @BreezyMontana_
Trademark: Innocuous lyrics and creative headgear
Recommended track: “Ball Out”


More cerebral and sonically experimental than drill or bop, this rap style is known for its insightful lyricism.

Chance the Rapper

Since releasing his 2013 mix tape, Acid Rap, Chancelor Bennett has collaborated with stars such as Skrillex and the British producer-singer James Blake.

Age: 21
Twitter: @chancetherapper
Trademark: Off-kilter samples and pithy bons mots
Recommended track: “Juice”

Vic Mensa

Friends and competitors, Chance and Mensa are both members of the same crew.

Age: 21
Twitter: @VicMensa
Sample lyric: “I’m Pacquiao on the track, flow the tempo you should tap it.”
Big break: A tour with the British dance duo Disclosure
Recommended track: “Down on My Luck”

Saba Pivot

Saba appears on Chance’s Acid Rap track “Everybody’s Something”

Age: 19
Twitter: @sabapivot
Trademark: Incisive lyrics paired with soulful live instrumentation
Recommended track: “Secondhand Smoke”

Alex Wiley

Chance makes a guest appearance in Wiley’s 2013 song “Mo Purp.”

Age: 20
Twitter: @alex_wiley
Sample lyric: “Then there’s me, pinch of Swayze, little bit of fuckboy, pinch of lazy. Little bit of genius, a pinch of crazy.”
Recommended track: “Vibration”


Age: 19
Twitter: @dreezydreezy
Trademark: Clever wordplay with ferocious delivery
Recommended track: “Schizophrenia”


Age: 19
Twitter: @official_tink
Trademark: Thoughtful R&B and hip-hop hybrids
Recommended track: “Don’t Tell Nobody” (featuring Jeremih)

How to Catch a Show: Follow these young MCs on Twitter (handles listed above), where they often announce last-minute shows and new music.

More to Watch: Lady drillers Katie Got Bandz and Sasha Go Hard … Drill vet King Louie … Englewood drill up-and-comer Spenzo … Alternative rappers Jean Deaux, Joey Purp, Kami de Chukwu, Lucki Ecks, Mick Jenkins, NoName Gypsy, and Rockie Fresh … Soul sampler Tree … Punk rocker ShowYouSuck


What are they up to?

Common: To benefit disadvantaged youth in Chicago, the Chatham-born rapper is sponsoring the Aahh! Fest, a new hip-hop festival that runs September 20 to 21.

Lupe Fiasco: The West Side–raised rapper is gearing up to release Tetsuo & Youth, his first new album in two years.

Kanye West (At rightBelow): Kim's new hubby is rumored to have an album in the works.

Photo: Antonio Perez/Chicago Tribune


Beyonce, Kendrick Lamar, JayZ
(From left) Beyoncé, Kendrick Lamar, Jay Z  Photos: (Beyonce, Jay Z); Matt Sayles/Invision/AP; (Lamar) courtesy of artist

Critic’s Picks

June 29

Bone Thugs-n-Harmony

7:30 p.m., House of Blues
The quintet behind ’90s gems like “1st of tha Month” and “Tha Crossroads” teams up for a reunion tour. $42. houseofblues.com

July 20

Kendrick Lamar

8:30 p.m., Pitchfork Music Festival
The introspective Compton rapper is still touring off the strength of his 2012 instant classic Good Kid, M.A.A.D City. You won’t have any complaints, though. Live, Lamar’s a firecracker who knows how to energize a crowd. $60 per day, three-day passes sold out. pitchforkmusicfestival.com

July 20

Schoolboy Q

4:15 p.m., Pitchfork Music Festival
Kendrick Lamar’s goofier label mate has plenty of party tunes to keep the energy high. Expect a joint performance of their raucous single “Collard Greens.” $60 per day, three-day passes sold out. pitchforkmusicfestival.com

July 24

Beyoncé and Jay Z

8 p.m., Soldier Field
Beyoncé’s steely flamboyance paired with her husband’s nonchalant cool makes this concert—if you can snag a ticket—the hottest one in any genre. $55 to $1,195. ticketmaster.com

July 25

Jurassic 5

7:30 p.m., Aragon Ballroom
L.A.’s alternative hip-hop troupe will dust off its high-tops this month and bring back the beats after a seven-year hiatus. $33. jamusa.com

August 2


8:30 p.m., Lollapalooza
By far the most anticipated rap reunion of the year, hip-hop’s oddballs Andre 3000 and Big Boi reunite after a six-year hiatus. But will the EDM-loving, neon-wearing Lolla crowd know the words to any songs besides “Hey Ya!”? $100 per day, three-day passes sold out. lollapalooza.com

August 3

Run the Jewels

3:45 p.m., Lollapalooza
If the rapping thing doesn’t work out for indie MCs El-P and Killer Mike, the musicians could take their comedy on the road. $100 per day, three-day passes sold out. lollapalooza.com


August 3

Chance the Rapper

8:30 p.m., Lollapalooza
This Chicago darling (see “Rappers on the Rise”) reaches even higher heights with a headlining slot at this year’s summer music behemoth. $100 per day, three-day passes sold out. lollapalooza.com

August 12

Kevin Gates

8 p.m., Reggie’s Rock Club
The up-and-comer from Louisiana croons like Auto-Tune rapper Future but spits like vintage Nas. $15 to $20. reggieslive.com

August 29

Action Bronson

North Coast Music Festival
Expect a wild show from this 260-pound Albanian American MC, who loves weed, cannoli, and jumping into festival crowds. $149 three-day pass, $279 VIP three-day pass. northcoastfestival.com

August 30

Kid Cudi

North Coast Music Festival
The one-time Kanye protégé has inherited his mentor’s taste for both spectacle and outré fashion. $149 three-day pass, $279 VIP three-day pass. northcoastfestival.com

Photo illustrations: Andrew Davis