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.
Drill
This Englewood-born minimalist gangsta rap goes heavy on the synth and snare, with lyrics often taking a back seat.
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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”
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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”
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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”
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Lil Bibby
Age: 19
Twitter: @LilBibby_
Big break: A cosign from Canadian rapper Drake
Recommended track: “Tired of Talkin’ ”
Bop
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.
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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”
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Dlow
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”
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Lil Ceno and Lil Trav
(Sicko Mobb)
Ages: 21 and 19
Twitter: @sickoworldfp
Big break: Signed to Sony/ATV last December
Recommended track: “Fiesta”
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Breezy Montana
Age: 24
Twitter: @BreezyMontana_
Trademark: Innocuous lyrics and creative headgear
Recommended track: “Ball Out”
Alternative
More cerebral and sonically experimental than drill or bop, this rap style is known for its insightful lyricism.
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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”
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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”
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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”
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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”
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Dreezy
Age: 19
Twitter: @dreezydreezy
Trademark: Clever wordplay with ferocious delivery
Recommended track: “Schizophrenia”
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Tink
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
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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.
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Critic’s Picks
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
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
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
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
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
Outkast
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
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
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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
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
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
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