Chicago rapper Kidd Kenn set for Lollapalooza debut

The gay rapper from the South Side felt like he “made it” after getting the call that the mega-music festival was interested.

SHARE Chicago rapper Kidd Kenn set for Lollapalooza debut
Kidd Kenn is a 20-year-old rapper from Chicago’s South Side. 

Kidd Kenn is a 20-year-old rapper from Chicago’s South Side.

Courtesy of 4th & Broadway/Def Jam Recordings

From a young age, Dontrell Smith knew that he wanted to see his name in lights.

And now, Smith — or Kidd Kenn as he is known — is making his Lollapalooza debut later this week. The 20-year-old openly gay rapper from Chatham is loud and proud about who he is and where he’s from, with his quick-witted, raunchy lyrics and effortless flow.

Kenn started making his own music in middle school. He’d remix popular songs from other Chicago rappers, like FBG Duck’s “Slide,” and put his own lyrics and unique style over the beat.

Being able to perform at Lollapalooza makes Kenn feel like he’s “made it,” especially being from Chicago, he told the Sun-Times via Zoom while on the set of the music video for his new single, “Coming.”

“That was crazy,” an all-smiles Kidd Kenn said about receiving the phone call to perform at Lollapalooza. “I love being face-to-face with the fans and just having a good time, making moments to remember. I love making memories.”

Kidd Kenn attends the 2023 Stonewall Vision Awards at The Ziegfeld Ballroom in June in New York.

Kidd Kenn attends the 2023 Stonewall Vision Awards at The Ziegfeld Ballroom in June in New York.

Santiago Felipe/Getty Images

Kenn grew up on the South Side with a “really big family.”

“Every day was always something different and it was just so much fun,” he said, noting that his community was always supportive of him, even after he came out. “I was just a regular kid going to school, doing regular kid things.”

He used to wonder how his family and friends would feel about him being gay, he said.

“But I don’t give a f- - -. I came in this world as myself and I’m going to leave as myself.”

The rapper now leans into femininity with an oozing, unapologetic confidence.

Kidd Kenn, who said he “got [his] name from being a Barb” (a nickname for fans of Nicki Minaj), quickly went viral online as a youngster for his “Freestyle Fridays.” Eventually, he cashed in the popularity and dropped his first EP, “Childish,” in 2018. In 2020, he released his second project, “Problem Child.” And last year, Kidd Kenn’s “Grown” EP signaled his ascent into adulthood.

Kenn can be heard on the soundtracks of two popular sports games, too: his song “Good Day” is a featured track on “NBA 2K23,” and “Get Lit” is on EA’s “Madden NFL 22.”

And in an exclusive collaboration with Target, Kidd Kenn earlier this month dropped a “Best of Kidd Kenn” vinyl box set that comes with a doll modeled after his own likeness. The doll’s hair even changes from pink to blue based on the temperature, to mimic Kenn’s ever-changing hairstyles.

“It was always in the back of my mind, like, ‘One day I’m gonna have a doll,’ ” he said. “But the fact that it happened so fast ... I love it, to be honest.”

He’s the first openly gay artist to have a doll on Target’s shelves, but the real Kidd Kenn can’t be put into a box.

“I can do anything and be 100% my authentic self,” he said. “It’s just so fun and it feels so good.”

Kidd Kenn will be performing at Lollapalooza at 6:50 p.m. at the BMI Stage on Thursday.

The Latest
The man tried to choke the woman he was arguing with, and she stabbed him in the neck, police said.
The faux flower installations have popped up at restaurants and other businesses in Lake View, Lincoln Park, the West Loop and beyond, mirroring a global trend.
Mayor Brandon Johnson’s latest initiatives don’t address concerns raised in a lawsuit against the city and provide no reassurance the city will get accessible housing right going forward.
Expanding insurance coverage of high-priced injectable weight-loss drugs for state workers will cost taxpayers $210 million in the first year of the initiative. But at least one economist says that estimate is way off and is expected to be millions more.
Prosecuting Assange would pose a grave threat to freedom of the press by treating common journalistic practices as crimes.