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For as long as he could remember, 21-year-old Taylor Bennett has always been known as ‘Chance the Rapper’s little brother’, but he’s ready to shed the little bro moniker and is poised to step into his own spotlight as the Chicago rapper opens up about the city he grew up in.

As any Chicagoan could tell you, growing up in the Windy City is no easy feat, especially for those who come from a less than fortunate background. Having been born and raised in the southside, West Chatham specifically, Bennett understands this all too well. But he never let the bad outweigh all the good his city had to offer.

“Anywhere in Chicago is kind of a struggle to grow up, but as a kid there were a lot of different activities,” Bennett explained. “There’s a lot of different things going [for it] such as art; there are a lot of musicians that came from down south that are pretty predominant in Chicago. I’m glad I grew up there.”

Another local favorite that many have probably heard of from the film of the same name is Wicker Park. According to Bennett the neighborhood serves as a great source of inspiration because of all the cool people and stores in the area. “There’s so many different artists and so many different fashion boutiques and all kinds of different exotic foods that you can just walk into at any moment,” Bennett said. “Because this place has so many things to see, so many things to do, it always inspires me to do much more as an artist.”

That inspiration has led Bennett to become the rapper that he is today as his recording career began not too far from Wicker Park. Bennett still records in the same studio he’s been using since he was 14-years-old, and for good reason. It’s the same studio that many prolific Chicago artists have recorded in like his brother Chance, Vic Mensa, and Tyler the Creator. “I know Kanye West did some track outs for ‘My Beautiful Dark Twisted Fantasy’ there, Twista, and a lot of Chicago artists,” Bennet explained.

But nothing could ever replace the first venue an artists performs at, which, for Bennett, also happens to be the place where he had his first sold out show making it all the more nostalgic. Reggie’s Rock Club was the spot where both he and Chance had their first sold out show, but more importantly it was also the first venue in Chicago that allowed independent hip-hop artists to perform there. “I think I’ve played at Reggie’s at least 20 times. I’ve headlined there at least five times. We still play there because it still means a lot [to us],” Bennett admits.

It’s this feeling of being true to yourself and your fans that Bennett strives to achieve every single day. Even when learning something new, like riding a motorcycle, he compares it to any other life experience because it’s both scary and exhilarating at the same time.

“The first time that I got on [the Honda Rebel] it was scary because you start to realize that it’s about control, but I think that’s very similar to how life is,” says Bennett. “You’re never really in control, but once you put your best two feet forward and you start believing in yourself then the next thing you know you’re just taking off and there’s just a lot of freedom in it.”

Perhaps being a newly minted motorcycle driver will help Bennett further carve a footprint in whatever lane he chooses to pursue, be it musically or otherwise.

  • Director: Keith Cecere
  • Producer: Meredith Hellman
  • Videographer: Mike Handler
  • Photographer: Daniel Peter
  • Stylist: Corey Stokes
Words by Daniel So
Branded Content Editor

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