Chicago rapper Taylor Bennett nods to his roots with a free show at Lincoln Hall Friday, the final stop on his "Be Yourself, Be A Champion" tour. // Courtesy of Taylor Bennett / Shore Fire Media

Chicago rapper Taylor Bennett on his free show Friday, lessons he learned from big brother Chance 

While rapper Taylor Bennett was crossing the country on his recent “Be Yourself, Be A Champion” tour, he always knew he had his final tour stop to come back home to.

On Friday, Bennett celebrates his homecoming — and his latest album release “Coming of Age” — at a free show at Lincoln Hall with a nod to his roots.

“When I do Chicago shows, and especially this Chicago show, I’m just super excited for it, because it’s a thing where my friends, my family, my teachers, my peers that I went to school with, those are the people I’m performing for,” Bennett, a bundle of infectious energy, explained.

“We’ve just been all over the country on this tour. ‘Kelly Clarkson,’ ‘Good Morning America.’ But now this is my show. These are the people that I really want to go above and beyond for.”

Bennett said his musical tastes were eclectic when he was growing up. It’s not hard to see how that influenced his latest release, “Coming of Age.” // Courtesy of Taylor Bennett / Shore Fire Media

Bennett said growing up in Chicago with his big brother Chance (as in Chance the Rapper), music was an escape for both of them.

“When I was a kid, I put on my headphones and I’d skateboard and it would just transport me to a whole other place, man. No matter what was going on, no matter what the vibe was,” Bennett said.

And as he recounted some of the favorites he had loaded on his iPod at the time — Regina Spektor, the Smiths, Simon and Garfunkel, Tracy Chapman, James Blake, Radiohead and Taylor Swift (“‘Shake It Off’ was one of my favorites!” he said.) — it’s not hard to see how he conjured up the eclectic sound on this spring’s “Coming of Age.”

At its core, the album is a rich dive into Bennett’s rap skills, but it also showcases his pipes as he swaps back and forth on the 11 songs in the collection. It’s a hip-hop album built on a rock base. And also pop-punk. And also R&B. And one song is straight-up emo off a teen movie soundtrack.

Collaborations can sometimes water down an artist’s vision, but this time around players including Matt Johnson (from indie-pop duo Matt & Kim), Tom Higgenson (from DuPage’s Plain White Ts), Jeremih, Mr. Hudson and others only strengthen Bennett’s theme, a walk through a catalog of his favorite vibes.

Sound unusual? You’re not wrong. But its unexpectedness works so well at amplifying his message for people who might not otherwise have an open door to explore it.

“I think the thing that a lot of times genre does is that it stops people from venturing. It gives them that barrier. It’s like, ‘This is what I like,'” he explained. “I felt like a lot of my friends didn’t listen to the music that I listened to. … But a lot of that music gave me the escape or gave me the opportunity to venture and learn more about myself. I didn’t have this barrier where I felt like ‘This is what I was supposed to do.’ And then, as I got older and I kept making music, I think something that I noticed is how many different folks don’t even realize that they have subscribed to some kind of programming in terms of what the expectations are for the music that they listen to.”

In addition to a load of Chicago-area artists kicking off the show, Taylor Bennett said he’ll be backed by a four-piece band Friday night at Lincoln Hall. // Courtesy of Taylor Bennett / Shore Fire Media

Bennett’s message has always been about challenging stereotypes and breaking down walls, with “Be Yourself” the title of his 2018 album released not long after he came out as bisexual. Now 26 and the father of two sons, he and his dad help comanage his brother Chance’s career (as well as his own) as independent artists.

“Me and my brother, we kind of crash heads over different things all the time,” he said. “But it also gives me (and him) the opportunity to hear out other perspectives, and maybe in a way that’s hard for others to get through to you.”

With music being a family affair, Bennett said Chance taught him a very important lesson — that sometimes what you represent to the people who support you can be more important than the music you’re working on.

“Understanding how your music can have a cause-and-effect on the people that are listening,” he said. “But bigger than the music, you’re making those statements, those opportunities. You get to say something for your community, for people, and using your platform to use your voice.”

Taylor Bennett’s musical message, most notably on his recent album “Coming of Age,” is about challenging stereotypes and breaking down barriers. // Courtesy of Taylor Bennett / Shore Fire Media

With his start playing open mics and speak-easies around Chicago, Bennett said he sees this Friday’s show as a chance to affect some change in Chicago’s independent music community, of which he’s always been a part.

“Everything is a 360, right? Because I performed at Lincoln Hall before, but now just taking in more America, I’m coming back just a little bit different,” he said. “Now how do I create those opportunities, maybe even at a bigger level than what I used to do when I did those speak-easies?”

Bennett’s show on Friday — during which he’ll be backed by a four-piece band — will also lead off with DJ Mike P, one of his former classmates. Bennett’s also opening doors for an “Emerging Acts” set with rising Chicago-area artists Cassius Tae, Chanelle Tru, Baha Bank$ and Recoechi.

“I’ve been super blessed. I feel like I’ve had so many fans that have been on the journey with me,” Bennett said. “I really gotta say thank you to Chicago on that.”

• • •

Taylor Bennett’s “Be Yourself, Be A Champion” tour

When: 6:30 p.m. Friday, July 22
Where: Lincoln Hall, 2424 N. Lincoln Ave., Chicago
Tickets: Free; RSVP at

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