The Next Generation Rapper


Taylor Bennett is in a jovial mood, and it’s refreshing. Necessary, even. It isn’t arrogance, but an infectious positivity. “Every time that I close my eyes and I look at the future, there are so many possibilities, and I just see brightness,” he says over the phone. “That’s why I’m still chasing my dreams; I know at the end of the tunnel, there’s something that I’ve been looking for forever.”

Now 20, Bennett was born and raised in Chicago, the younger of two sons. While his family background is in politics—his father, Ken Bennett, worked as an aide to Chicago Mayor Rahm Emmanuel and under President Obama when he was a senator—both Bennett and his brother, Chance the Rapper, are musicians. “My parents are good parents,” he says. “They like their kids to follow their dreams.”  

It’s easy to compare Bennett to Chance: they’ve collaborated with many of the same Chicago artists, including each other, and have a similarly playful approach to lyrics and production that sets them apart from many of their Chi-town predecessors. They’re also both very hard workers. “That comes from my dad and mom,” Bennett reflects. “Something my dad says is, ‘When you get to the point when you think that you’ve done everything that you can, you know that you’ve lost, because you can always do more. You can always work harder. You can always put in more time.'”

Currently, Bennett is working on a new album, a follow-up to 2015’s Broad Shoulders. Last month, he released a song with Stro and Jordan Bratton, “New York Nights,” and played his biggest headlining show to date in his hometown. “A lot of my music that I write is based on futuristic things that happen to me,” he says. “It’s hard to be honest with yourself as a person, but I’m very, very honest when I write my music, and maybe that’s why I see the future unfold after I release the track.”

AGE: 20.

HOMETOWN: Chicago, Illinois.

CURRENT LOCATION: Chicago, Illinois. I wouldn’t have it any other way. I know where everything is. [laughs] It’s just where I fit. It built me as a person. I wouldn’t be the same person I am today without the city of Chicago.

MUSICAL BACKGROUND: I never took music lessons or anything like that. Chance took some piano lessons as a kid, but me, it’s always been natural. It’s been something that comes to me. I’ve loved it since I was a child. My family loves music and we’ve always played music, from Jay Z to Coldplay to Erykah Badu. I grew up in a household where music was very much a backbone of our childhood.

DEBUT PERFORMANCE: The first time I ever had a show was with a pretty big group. I was nervous. I couldn’t afford to practice somewhere that had a microphone, so I’d been performing my vocals with a remote in my hand. I had my friend as a hypeman playing the instrumentals in the background. I was the first opener and there were about 30 people there—not too many.

A RAPID RISE: By my senior year in high school, I was selling out venues that held about 500, 600 people. I decided to run with it and go after it. It wasn’t just my parents, it was me too. I never wanted to wake up one day and go, “What if I had gotten on Sway and done the 10 Fingers of Death? What if I dropped an album that was premiered by Rolling Stone when I was 19, 20 years old? What if I was one of the most streamed Soundcloud exclusive artists?”

MUSICAL MANIFESTO: I make music to bring people together. I’ve known that since a young age. There’s a lot of people that make music to be relevant. There’s a lot of people that make music for money. There’s a lot of people that make music for fame. None of those things have ever been a variable for me in terms of writing music. I’ve always wanted to make timeless music. I made a tweet and I’ll never forget it, I said I’d make timeless music for funerals and weddings and I’m not ashamed of it. I want people to share an experience so when they look back in 30 years, they don’t mind that they paid a dollar for it, or got it for free, or had to go on these sites and look it up—when they hear that music, they remember a specific experience and what it was like at that moment in time.

LIFE AS INSPIRATION: Music is everything that I do and it’s everything that I see. Walking down the street right now seeing kids smile, seeing people open doors for different ladies, seeing taxi drivers pissed off because they can’t get into the next lane, that all inspires me.

THE IMPORTANCE OF FANS: I feel confident in my identity as an artist. What gives me that confidence is my fans, the people that I know that love and support me. Without your fans, your music means nothing; no one cares. It’s always about them. It’s never about how you feel as an artist, because you don’t make the music for yourself, you make the music for your fans. If people stopped listening, I’d probably still make music because at that point, I’d be writing to gain a new fanbase. I can’t say that one day people won’t be like, “You know what, Taylor Bennett, I’m not feeling this. I’m not liking this.” They might turn the radio off, they might stop going to Soundcloud and Spotify and checking out my music, but I can promise I’ll never give up as an artist because I owe them that.

CONSTRUCTIVE CRITICISM: [When I have a new track,] I play it to my manager, Joseph Cabey, every time. He’s not just my manager; he’s my best friend. We’re the same age. We’ve known each other since we were 16. He always gives his honest opinion. It’s not always positive. A lot of times I’ll give it to him and he’ll be like, “Yo, what is this? I know you can do better. I know you can change that chorus. I know you can switch these words around.” That happens more often than not and you need that, you need to be able to have constructive criticism. Every track that I write, every note that I play, it’s not going to be amazing the first time around. I would love if it was, but we’re humans, we’re not perfect.

THE ART OF COLLABORATING: I love collaborating. The reason I love collaborating is because I love pushing people to the next level. I like taking them out of their comfort zone. That’s what I try to do with every artist. I love Kendrick, I love Kanye, I love Jay Z, I love all of these people, but I’ve worked with my brother Chance already and in my idea of an artist, Chance is the most 100 percent natural, honest artist. We’re blood brothers, so we know each other the best, which means there’s a brotherly rivalry and I’ll always be able to push him more and he’ll always be able to push me more than any other artist. I’ve made that song already, but we have more songs to come in the future and I love collaborating with my brother.

BROTHERLY LOVE: My brother was like my dad for about two years. My dad moved to Washington, D.C., and Chance was the oldest father figure in the house. He took me under his wing. He always cared for me. I knew there was anything I could tell my brother; I could ask for anything and he’d always have my back. And now that I’m older, it’s the same way between both of us. If there’s anything Chance needs, he’ll call me. If there’s anything I need, I’ll call Chance.

THE TWO SIDES OF TAYLOR BENNETT: I’m happy, but there’s two different Taylor Bennetts—there’s the artist, and there’s my personal life. We all go through things—trials, tribulations—and that fuels me to write music even more. Everything’s not glitter and glamor; there are days when you feel dark, you feel sad. A song that a lot of my fans like is called “Dancing in the Rain” off of my last album Broad Shoulders. At that point in time, I was at a pretty deep and dark point in my life, but that’s what gave me the fuel and the emotion to actually channel into that song.

GETTING RECOGNIZED: It’s love to be able to walk down the street in your city and have people stop you and want to talk to you, to be able to have conversations. It’s a total difference from being 14, 15, people looking at you and not knowing you. Now to be at this level of acclaim is amazing.

LOOKING BACK: I play my old music all the time. What I like about it is that there’s a form of innocence that’s hard to get back. It’s hard to be able to rap and say things so unconsciously and not think about everything and everyone’s opinion. When I was a kid, I was creating and building my image of who I was as an artist, so those were the days that were most impactful. It’s good to go back there and be able to say, “Wow, that was really good.” I don’t regret it. I’m glad I started at such a young age.


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