It’s not everyday that a Chicago teen gets to open a concert for a rapper like Nas. But that’s what’s happening Saturday night for Taylor Bennett, the 18-year-old lyrical phenom who just so happens to be the little bro of Chance the Rapper, just so happens to have premiered his latest video on MTV.com and who this year, just so happens to have already sold out three shows in Chicago alone.

Kanye, Common, Twista, Chance, Louie, Keef, Herb, Lupe and Katie all make headlines and keep Chi-town hip-hop front and center. It looks like Taylor’s turn is next. “It’s all about the future,” says the Urban Prep grad, who recently graduated and says he was accepted into several colleges, including Western Illinois University. He’s skipping college for the moment so he can work on more music and nonviolence campaign #savechicago. Adds Bennett: “It’s all about the next generation of Chicagoans and how they will act and how they will be perceived.”

Watch Adrienne Samuels Gibbs’ exclusive interview with Taylor Bennett below or scroll down for the rest of the story.


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Bennett is 18, eloquent and stylish as he sits in a near West Side studio, tweaking a song while his manager and a sound engineer look on. He’s also unabashedly 100% Chicago with a LDRS hat cocked atop his head, Bucketfeet shoes on his feet and pockets ready to donate cash to Roseland charity Kids Off the Block.

Last Saturday, in fact, Bennett rocked out a crowd at Reggie’s on south Michigan, with all proceeds for KOTB, which really does get kids off the block. He performed his newest hits, including “New Chevy,” featuring Chicago rapper King Louie and other songs off his ecclectic mixtape “Mainstream Music.” It’s likely he’ll perform some of the same when he opens for Nas at a sold-out, official Lollapalooza after show kicking off at 10 p.m. Saturday night at the House of Blues.

Enter to win tix to Lolla Aftershow

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You might think that Bennett got a leg up because of his brother. But the truth is, not so much. Like any other big brother, the elder Bennett told the younger Bennett to work it out on his own.

“I wanted his help at first and he kind of had a talk with me and told me ‘man, I want you to make it on your own. I want you to sell out shows by yourself. I’m not going to be tweeting out your stuff,’” says Bennett, remembering a conversation the brothers had when he was 14.

Four years later, Chance apparently still sticks to his word. “He’s never tweeted out my songs,” says Bennett. “At first I was like ‘Chance, I’m 14 and you’re telling me you’re not gonna help me?!’ And now I’m in this chair and we have millions of views with videos and songs. Life is crazy when you work for it and I appreciate my brother for teaching me that lesson.”

Perhaps you already know the Bennett story. If not, here’s a short recap. Chance and Taylor are the sons of Ken Bennett, who currently works in the Chicago mayor’s office as deputy chief of staff. Previously, Mr. Bennett worked with President Barack Obama in a number of positions. Mom Lisa is a fixture in her son’s lives, and in the past has been reported to be an employee for the Illinois Attorney General’s office. Older brother Chance has had amazing success as a breakout Chicago rapper. And now the younger Bennett, a vocal member of a church on the far South Side in Roseland, got next. He grew up between Chatham and Roseland and counts both R. Kelly and Twista as amongst the Chicagoans whose art he respects. He fully supports all Chicago hip hop, and like Common just did, reached out to a variety of local stars for features on his mix tape.

fxtaylor-CST-080114 6.JPG Of course, given the variety of music found on “Mainstream,” what he really wants to do now is figure out – like most teens – who he is and where he’s going. He’s also interested in happy music, a la the Pharrell-method-of-making- millions. ”

“I’m focusing on who is Taylor Bennett, what does he want, what does he think is right and what does he think is wrong,” says Bennett, referring out loud to himself. “I also want to make some positive music because not only is positive music good, but it also sells. Everybody wants to be happy.”

True that. And with his participation in #savechicago he’s also winning over even more fans.

Watch “New Chevy”

“The kids, some of them are fans of Taylor’s,” says Diane Latiker, founder of Kids Off the Block, which provides alternatives for youth up to 24 years old. “They can’t believe he’s donating his proceeds. What he’s doing makes a difference. What I’m doing may not impact millions, but it will impact some, who will impact others. I believe in the power of one. It’s cool that young people are giving back and that needs to be seen more, especially in his capacity.”

It’s unclear how many downloads were made of “Mainstream Music,” but “New Chevy” is going on 51,000 views on Youtube. And the song “Creme Brûlée,” featuring Lil Herb, is getting good feedback from fans. It’s also unclear how much money will be donated to Kids Off the Block. Once totals are in on all fronts, this post will be updated.

[Explicit language – not appropriate for children or for work] Listen:

fxtaylor-CST-080114 3.JPGEnglewood-based producer Saint the Good Boy, aka Lennell Davis, worked on about half of Bennett’s latest mix tape. He echoed Bennett in saying that the music, right now, is a little bit of everything and eventually it will mature into a new sound.

“He has a vision for what he wants,” says Davis. “He knows his sounds and a little bit of business, so it kinda put him ahead of the game ahead of a lot of artists in Chicago.”

Bennett acknowledges he’s had a few “swings and misses” in his releases, but he wouldn’t change the way he’s done a single thing. “If I didn’t do what I did, I wouldn’t be here,” says the artist, who is currently unsigned. “Standing on your own twos are what makes the difference.”

— Adrienne Samuels Gibbs