Chicago Rappers Pop Out at Lollapalooza

Mike Milo

When Lollapalooza first toured the country in 1991, the closest thing to hip-hop on the bill was Ice-T’s heavy metal band, Body Count. In the ensuing decades, the festival has settled into a permanent home in Chicago’s Grant Park as hip-hop has become the center of the music industry. This year’s lineup included A-list rappers Lil Wayne and Meek Mill as well as hip-hop-indebted acts like Ariana Grande, J Balvin, and 21 Pilots. While the festival needs to improve on booking local acts (only 5% of the lineup), the hometown rappers at this year’s Lollapalooza provided a compelling snapshot of Chicago hip-hop’s present and hinted at its future.

Saba returned to the festival for the first time since performing in 2016, which came three years after Chance The Rapper released Acid Rap and a few months before his own debut album. The set felt momentous enough for him to boast about it on 2018’s “PROM/KING.” Since his Lolla debut, the West Side native has toured relentlessly behind two solo albums, a group mixtape, and a slew of features. As the Chicago Tribune’s Greg Kot noted, Saba now draws enormous crowds, eager to dance and rap along to his dense, heartfelt verses.

Saba’s years on the road are evident; he commands the stage like a veteran, professional yet passionate. He dispensed his dextrous bars smoothly with minimal backing vocals. Between songs, he told the crowd he wanted the show to “feel like a homecoming,” then played through a variety of grooves like the ideal DJ. Saba rapped “MOST” over a house remix, and found triumph in the ominous skittering of “LIFE.”

Saba also seamlessly worked his guests into his set. Smino sang “World In My Hands” and Revenge Of The Dreamers III closer “Sacrifices.” As Smi walked offstage, Saba proudly dubbed him “a Chicago legend.” Pivot Gang members Frsh Waters and MFnMelo ripped through their verses, and Saba’s brother, Joseph Chilliams, shimmied through his harrowing verse on the mosh-inducing “Westside Bound 3.” Their performances only hinted at the camaraderie in store for a future Pivot Gang tour. Saba is a star, and he's shining on the excellent artists in his orbit.

Polo G’s recent debut, Die A Legend, shows the same emotion and attention to detail as Saba’s albums, even if the sonic palette is closer to drill. The breakout North Sider was added to the festival’s lineup just three hours before his performance on Friday as a replacement for Rich the Kid. Though it was great to see another local rapper on a prominent stage, the late announcement caused fans to scramble to catch the set. One wonders why Lolla organizers didn’t book Polo in the first place.

Still, Polo G rose to the occasion. He opened with “Through da Storm,” rapping about hustling as a substitute for an allowance and overcoming depression through his subsequent riches. At times he was too reliant on a vocal backing track, noticeable when his live voice didn’t match the sheen of the studio. Still, he was an impressive presence, especially considering he has yet to start his first tour. The joyous mayhem spurred by his hit “Pop Out” confirmed this would not be Polo’s last festival appearance.

Coincidentally, Calboy is the only other Chicagoan who’s risen as quickly as Polo in 2019, thanks to his hit “Envy Me.” Unfortunately, he perpetuated one of the worst cliches of rappers at festivals: a ten-minute introductory DJ set that relied on a rote set of turn-up tracks (“Faneto,” “Look At Me,” “Shabba”). This decision was especially frustrating since his debut project, Wildboy, is strong enough to carry a full 45-minute festival set.

The wait was worth it once Calboy, decked out in a red, yellow and purple striped tracksuit, burst onto the stage. His live performance was so energetic, he often had to rely on the crowd to finish a bar while he caught his breath. On “Chariot,” his voice was the perfect timbre to cut through bellowing bass. Calboy has toured with Kodak Black and 21 Savage in the past, but the Lolla audience was another beast. “Back home, they sang every word to every song,” the rapper said after his set. “It gave me a different type of energy.”

Calboy’s set included a welcome surprise appearance from Chance The Rapper, hours before he resurfaced with Death Cab for Cutie. The crowd roared along with his “No Problem” verse before he and Calboy debuted “Get A Bag,” their breezy song off Chance’s recent The Big Day. The two recorded together because they listened to each other’s music. The guest appearance was similarly simple: “I was just talking to him like, ‘I got the Lollapalooza, you mind if you show up at my show?’” Calboy said. “No question, he gon’ slide.”

Calboy explained that, beyond more collabs, he looks forward to Chance’s advice on charity work. “Because I know he’s good with it, especially the public speaking,” he said. “I want people to understand who I am. I’ma start letting my actions speak for me.” Calboy is interested in helping Chicago youth with mental illness after struggles in his past. “I want to help people identify those situations, those problems, and get over them,” he explained. “However I can do that, I’ma figure it out in crafty ways.”

It’s telling that Chance performed with Calboy, rather than past collaborators Saba or Childish Gambino. Calboy and Polo are part of a stylistically diverse new wave of Chicago rappers currently basking in attention from labels, journalists, fans and fellow musicians. (Calboy showed up on Meek Mill’s stage the day after he performed.) 

Today’s rising stars are looking to Chance and his peers as elder generation references for not just music but business and politics as well. Barring unfortunate exceptions like the exiled Chief Keef, they’re proof that musicians do not need to move to the other coasts to make an impact in music. Lollapalooza would be wise to show off even more of this local talent in 2020.

Calboy said it best as the crowd pulled back into mosh pits for “Envy Me”: “I just went double Platinum the other day. That’s a trophy for Chicago.”

Originally published on DJBooth.