Kidd Kenn holding a doll of himself from his "Best of Kidd Kenn" Target exclusive. Credit: Kenneth Courtney

GRANT PARK — At 20 years old, Dontrell Smith — better known as Kidd Kenn — is getting ready to perform at one of the biggest music festivals in the country, which also happens to be in his hometown.

The South Side native will be making his Lollapalooza debut Thursday. You can catch him live at the BMI stage beginning at 6:50 p.m.

This is not only Kenn’s first time performing at Lollapalooza — it’s also his first time at the festival.

“It’s so funny, before I started doing music, I never been to a concert outside of a show that I performed at,” Kenn said. “I still never been to one.”

Plenty of his family, including his mother and sisters, will be in attendance to watch him take the stage, he said.

Kenn signed with Island Records when he was just 15, and his star has only risen since. He has been acknowledged by Grammy-winning artists Megan Thee Stallion and Lil Nas X and profiled by the Recording Academy. He’s even released his own vinyl and doll box set.

With over 500,000 followers on TikTok and 200,000 on Instagram, Kenn has had his share of viral moments. In 2021, he became the first openly gay rapper to participate in a BET Hip-Hop Awards cypher.

“When I got called for the cypher, when I tell you I was so f—n excited, ’cause that was literally on my bucket list. I was just ready to show them why I was here to stay, and that’s exactly what I did. They said I did the best,” he said.

Despite the attention at such a young age, Kenn said he always felt confident when it came to music and doing the things he had dreamed about growing up.

“I just know I’m raw as s—. I don’t need nobody’s validation, I don’t need nobody’s approval,” Kenn said. “Me looking at my younger self, I always wanted to do s— like this. I always wanted to perform on the Lolla stage, so I just knew it was gonna happen one day.”

His confident personality oozes through in his music. His 2021 track “Good Day,” which has nearly 1 million streams on Spotify, opens like this:

You need somebody that asks you “yo how you feeling?”
I walk around with my confidence on a million.
Don’t let it bother me when the people be trippin’
Imma have a good day

Kenn cites Chicago artists like G Herbo and King Von as inspiration for his music. His stage name comes from his admiration of rapper Nicki Minaj, who calls herself Barbie, as well as from Barbie’s companion, the popular Ken doll.

Coincidentally, on the day of Kenn’s interview with Block Club, he was going to see the new “Barbie” movie. He jokingly wondered why he wasn’t asked to be in it.

“They should’ve called me for this one … I for sure better be in the next one,” Kenn said.

Ahead of his Thursday performance, Kenn dropped a new track titled “Coming” that’s featured on his upcoming EP, “Busy Being Bad,” due out Aug. 18.

Kenn said he’ll play new, unreleased music during his Lollapalooza set.

He’s more than ready, he said, reflecting on the work he’s put in to reach this point.

“When I was younger, everybody was outside, being kids. I was thinking how I’m gonna be chilling when I’m 30. I just saw where I came from and I just thought that everything just repeated itself,” Kenn said. “Everybody just woke up and did the same s— every day. I just knew it was much more to life and I wanted to see it.”

Single-day tickets are still available on the Lollapalooza website.

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