Taylor Bennett In His Own Words

The same could be said for Taylor Bennett, the 21-year-old Chicago rapper whose tour bus had been co-opted by Bomber. Bennett had just embarked on his first headlining tour when I met up with him in April, and he's still getting used to the chaos. There are anywhere from 20 to 30 people hopping in and out of the bus throughout the night; smoking cigarettes outside, waiting to take a shower in the tiny bathroom in the back, changing into a new pair of sneakers, ordering Chinese food. Everyone seems to be a part of an extended Chicago family, whose members are under the age of 24 and really, really excited to be there. It's unclear who, exactly, is in charge. I quickly lose track of who's opening for who and who's DJ'ing for which rapper. I ask Jordan Bratton, one of Bennett's artists who is featured on his song "New York Nights," if he's performing later. He shrugs, "Not sure! Maybe! Why not?" (he did).

I had plenty of time to soak in the chaos too because Bennett arrived two hours late to meet me at the tour bus. He showed up riding a hoverboard, wearing a white tee-shirt and a huge grin. A Marlboro Red stayed tucked behind his ear for most of the night. He looked genuinely thrilled to be back on his tour bus, despite it being full of people, many of which were strangers, blasting Drake.

Bennett was on his first tour for his sophomore album, Restoration of American Idol, which he released in February. The record includes plenty of upbeat, poppy songs featuring big name artists, like Neon Lights with Lil Yachty or Nobody Tell a Name with Raury. But it's on the more soulful and contemplative tracks where Bennett's personality starts to emerge as something more adult:

"My shoulders got broader, my music got smarter," Bennett raps on the intro track. "I work like this shit is a privilege"

In the midst of a spaghetti dinner on the back of the tour bus, Bennett told me Restoration is his most personal project yet. "A lot of people have been waiting to see who I am," he said. "A lot of labels have been slapped on me—like oh he's just Chance the Rapper's younger brother. That makes people wonder, what does he have to say, what does he feel like, what is his music really about?"

Restoration is Bennett's attempt to tell you. He discusses fame, yearning for recognition, and the struggle to find authentic relationships along the way. Bennett's voice comes through clearly and confidently. He raps the way he talks—fast and joyfully. Several times he's laughing on the track and you can almost hear him smiling in the booth.

Restoration is also enchanting for its consistent down-tempo melodies. It's a whirlwind of sounds and textures but all of the songs stay entwined, concise, and mellow the whole time. On most of his songs, he's rapping slightly faster than the underlying beats—most of of which are instrumental and sound like they have the backing of a live band. The sound is somewhat reminiscent of his Chicago peers, like Kweku Collins, The O'My's, and Kids These Days. But the most interesting and distinct thing about Bennett's songs is his voice. It's low-pitched and alternately smooth and raspy (the Marlboro Reds might have something to do with that). It's entrancing when combined with the down-tempo trap drum lines and auto-tuned piano riffs. The nine tracks build upon each other, one by one.

Bennett grew up on south side of Chicago and has been making music since before he was a teenager. He started releasing it in 2013 with his mixtape The Taylor Bennett Show. In 2015, Bennett put out Broad Shoulders, a solid full-length album that brought him acclaim beyond the Chicago hip-hop scene.

Restoration isn't the only way Bennett is starting to reveal himself more. In January, Bennett came out as bisexual on Twitter. There was an ensuing flurry of headlines that served as a reminder of how male sexuality is still a strict taboo in hip-hop. But Bennett is the latest example of how that rigidity is changing. He joins a growing number of publicly out LGBTQ artists, including iLoveMakonnen, Le1f, Young Ma, and of course, Frank Ocean. When discussing the topic in past interviews, Bennett says he wanted to be an example to others of self-acceptance regardless of race, gender, or sexuality. There has been an outpouring of positive support from his friends, family and fans in response to that message, Bennett told me after his show.

But, as Bennett acknowledges, he's still often recognized as "Chance's little brother." It's understandably difficult to step out as an artist in your own right when you're coming from the same tight-knit Chicago music circle, let alone the same household as your extremely famous older brother. Bennett says as much on the first track on Restoration, "I had to show him that I'm not lil' bro," he raps. This, coupled with Chance's meteoric rise to fame over the past several years, might make some 21-year-olds wary of the constant comparisons. But Bennett is cheerful and philosophical about the whole thing.

"A realization I had a long time ago is that no matter what I'll do I'll always be Chance's brother," Bennett tells me. "It doesn't matter if I get bigger than Chance, or if I just stay me…I'll always be his brother."

Brotherly love aside, Bennett is ready to step out of Chance's shadow. And apparently people are starting to respond. "It's been like almost a year since people have stopped coming up to me and saying, 'oh Chance the Rapper's brother, I came to see you cause I saw you were in town!' " Bennett says. "Now it's more like, Taylor I love your music!" He told me his fans knew the words and were singing along even on the first stop of his tour.

That's not to say the two brothers steer clear of each other's work. The first time Bennett and Chance collaborated was on the title track of Broad Shoulders. On the song, the two go back and forth giving each other advice while acknowledging that neither of them are quite ready to take it. It's a heartfelt exchange, full of Chance's musings about becoming a father (his daughter was born around when it was recorded) and Bennett's hook; "Reach for your goals, hear what you're told/think that you know." Bennett's fast-paced raspiness is a welcome complement to Chance's down-tempo verses.

The two appear together again on Taylor's latest album on the song "Grown Up Fairy Tales," produced by Mike WiLL Made-It and also featuring Jeremih. Bennett told me the track was originally made over two years ago and intended to go on Chance's second album, Acid Rap. The message is entirely different from Broad Shoulders, but like so much of Bennett and Chance's work, it centers on family.

"The perspective was from my granddad seeing [my grandmother] pass away," Bennett told me, describing his verse. "But it's really a man's perspective watching a woman he loves pass away. It's my favorite song Chance has ever made."

Grindin' so strong I can't fathom condolence/
You used to hold me down and that was my lonesome/
And now I call your phone from voicemail recordings/
A preview of my previous favorite woman/

Bennett is an independent artist, who like his brother, has refused to sign to any major record label. Not only does this mean he can retain complete ownership over the masters to his recordings, Bennett also gets to decide how, when, and where to release his music. It also means there aren't any adult label executives setting up or overseeing his tour, which is probably why it feels a bit like a traveling circus. But Bennett is deeply proud of his independence and the ability to have complete creative control over what he does.

"There is a huge difference when you own something and knowing that you own it versus knowing you're in debt for something that you possibly could've done by yourself," he said.

The young rapper is unusually enthusiastic discussing the business side to his music. When we start talking about the pros and cons of signing to a label, Bennett's face lights up. He begins rattling off terms like "360 deals," "EPK," "streaming placements," "platform publishing," and "brand partnerships."

"I understand how to read split sheets, I understand royalties, masters, publishing, all the mechanics," Bennett tells me. "You know we do swaps with other record labels all the time."

He continues: "A lot of artists just wanna be able to say 'oh I'm on this big tour bus', 'I wanna go out, go to the club, buy clothes and be poppin'. I'm like, nah," Bennett says laughing. "Cause the thing is that I love money way more than that." While a lot of young artists are eager to sign with a label for the promise of security, they often see very little of the profit or have ownership over their own music in the end. Bennett seems to be keenly aware of this. He, along with his manager, formed his own mini-label for himself, Tay B Entertainment as a way to ensure their financial and artistic independence. They partner with streaming services to release music and work with booking agents to throw their own shows in order and ensure they get paid directly.

That night in early April, Bennett was playing at the legendary New York City hip-hop venue, SOB's. It was clearly a measure of success for the young artist. Whenever he started talking about it (which was often) he became giddy.

"I love SOB's!" Bennett tells me, his face lighting up. "SOB's is the pivotal point for an artist from Chicago, or honestly anyone else that's not from New York, you have to sell that shit out. Once you sell out SOB's it's a monumental moment. I'm very prideful of it." That much is clear; Bennett mentions the venue on the second line of his song Neon Lights, rapping "Me and Supa Supa sold out SOB's, New York," referring to last summer when he first played there with fellow Chicago rapper Super Bwe. He sold it out again on this tour. Bennett told me he was debating whether to repeat the line during his performances to emphasize this milestone has now been achieved—twice.

Ryan Jay is a photographer based in New York. Find more of his work on his website.

Olivia Becker is a freelance writer. Follow her on Twitter.