Facing the music: Taylor Bennett

By / Cover stories / February 24, 2017

Chicago rapper Taylor Bennett steps out of his brother’s shadow with a new EP

Pants: A-COLD-WALL*, $300 Shirt: J.W.Anderson, $335 Both available: Barneys New York, 15 E. Oak; Barneys.com Jacket: Marc Jacobs, $850 Sneakers: Adidas X Raf Simons, $415 Both available: Urban Oxygen, 230 W. Superior; Urban-oxygen.com


When Chance the Rapper took the stage to accept his Best Rap Album Grammy Feb. 12 — his third that night — he thanked his mother and father, who have both worked for Chicago local government, and his younger brother, Taylor Bennett.

The name may not have been familiar to many, but it soon will be. The younger Bennett, 21, released his first completely original album, “Broad Shoulders,” in December 2015 (and an accompanying short film of the same name last month); last summer, after selling out smaller shows in Chicago, he headlined a sold-out show at SOB’s, a popular New York City music venue. And this weekend, he releases his latest EP, “Restoration Of An American Idol,” featuring his second-ever collaboration with Chance produced by Mike WiLL Made-It, plus songs with artists like Raury, Luke Tennyson and more. “It’s my best work yet,” he says. “You really get Taylor on this project.”

Verse 1

When Bennett was 9 or 10 years old, before SoundCloud or Spotify or Apple Music existed, he heard a song that changed the course of his life: “Hope” by Twista — an ultra-fast-rapping artist from Chicago’s West Side — and Faith Evans. “Growing up on the South Side of Chicago, going outside every day there’s a possibility you don’t come back,” Bennett said in a radio interview last summer. “So when I first heard that song … it inspired me and it made me want to push, because this music could literally take me away.”

So that’s exactly what he did. When he was 15, he was freestyle rapping with some friends on the corner of Chicago Avenue and State Street when he met Joseph Cabey, now his manager and one of his closest friends. “He’s the best freestyler I’ve ever met,” Cabey says. “Everybody knows that.” He encouraged Bennett to get into the studio, and they landed at Classick Studios, a humble outfit in Humboldt Park, to record his first single, “Speed Racer.” Six years and three albums (the first two largely sampled from other songs) later, it’s still the studio he spends most of his time in.


“My dad and brother and me have been saying for awhile now [that] there’s a renaissance going on in Chicago,” Bennett says. “I think anywhere that you find pain, anywhere that you find struggle, violence, you’ll find art.” He mentions the famous Martin Luther King Jr. quote — “Darkness cannot drive out darkness; only light can do that” — and goes on: “In Chicago we’ve seen so much and we’re still going through a lot, and [as artists] we have to speak to those things. I believe that me and Chance want to change more than just the industry, the music that’s on your radio. I believe we speak — or we try to speak — things into existence, and one of those things is peace and equality.”

And, in fact, Bennett’s lyrics, like Chance’s before him, aren’t about flashy cars or stacks of money — at least not dominantly. They’re about family, loyalty and the city that raised him: Chicago. “I lived in West Hollywood for two months when I was 18,” he says. “I didn’t really like it that much; I ended up moving back. I wouldn’t be the same if it wasn’t for Chicago. It’s the city I come from. Your first population of people who become your fans, [they’re] your backbone. … You need to have people that are always down to support you, and that’s why I love Chicago so much. They’ve seen me go through different areas of my life and always been there for me.”

Verse 2

One of the most unique things about the Bennett brothers is the way they distribute their music. Neither is attached to a major record label, and both release new songs and albums for free through the music-sharing program SoundCloud. Bennett even went so far as to create his own independent LLC, Tay Bennett Entertainment, and learn the ins and outs of the business: he handles the split sheets (a publishing document stating who owns the rights to a song), contracts with collaborators, marketing and distribution — industry elements most mainstream artists never have to stress over.

To make money, his songs are still available for download, for listeners who want to hear it in areas with no internet or cellular service. “I would like everybody to be able to hear my music,” Bennett says. “I don’t believe you should have to pay to hear something that is that pivotal or motivational to you, which I think my music is to a lot of my fans. However, you gotta respect the fact that it is a job, and you have to get paid for your work. You want to listen to my music while you’re on the train and you don’t want to worry about your reception? Cool, download [buy] it. But everyday, you’re working out, you’re at home doing homework, you shouldn’t have to pay to hear my music.”

Pants: Dsquared2, $775 Sweater: Marni, $975 Jacket: Y/Project, similar $975 All available: Urban Oxygen, 230 W. Superior; Urban-oxygen.com Cap: Polo Ralph Lauren, Bennett’s own


For those still wondering, Chance refused to let Bennett ride in on his coattails, encouraging him to earn acclaim in his own right. Sure, comparisons are inevitable — the two, less than three years apart, have a strong resemblance, and when Chance jumps in for a verse on Bennett’s “Broad Shoulders,” it’s tough to tell who’s who. “We’ll always have the same voice, just based off the fact that we’re brothers,” Bennett says. “But I like to think that the way we rap is different. Chance is one of the most dominant artists right now and to constantly be compared to him — if I made music and it wasn’t that good, just because I’m his brother people wouldn’t constantly compare; they’d be like, ‘This isn’t as good.’ So I think [the comparisons] show that we both have a work ethic like no other. … In my rap career I’m not competing with anybody but myself. But if we were talking about competition, I’m not competing against my brother. I’m coming after the Kanye Wests, and the Jay Zs. I’m reaching for the stars.”

At the shoot

We spent the morning with Chicagoan Taylor Bennett at the studio he’s called home since he started rapping at age 15 (he even cut his very first track, “Speed Racer,” there). He performed along to songs from his brand-new EP, giving Splash an exclusive first listen before the Feb. 24 drop.

Photographer: Maria Ponce
Styling: Luis Cruz, Ford Artists
Grooming: Lyneé Ruiz, Ford Artists
Shot on location at: Classick Studios, 2950 W. Chicago; Classickstudios.com

COVER | Shorts: Rick Owens Drkshdw, $415  Jacket: Marc Jacobs, similar $1,475  Both available: Urban Oxygen, 230 W. Superior; Urban-oxygen.com  T-shirt and necklace: Bennett’s own


You might also like

Leave a Reply

Your email address will not be published. Required fields are marked *