During an intimate dinner among journalists and Bennett's family and friends powered by Footaction on Thursday night at New York City's VYNL, Billboard spoke one-on-one with Bennett about his latest studio effort, owning his confidence on wax, coming out on Twitter earlier this year and why critics can quit referring to him as Chance the Rapper's little brother.
How would you define your personal style?
I like to think of it kind of mix-match. I got my green shirt on, my white jacket and pink shoes. Sometimes I'll pull the super Mr. Smooth guy. I'll do all black or all gray. Typically, I like to do myself. I like my clothes to kind of explain who I am. I don't like to be too dull. I like to be poppin'.
You recently dropped Restoration of an American Idol. Explain the title and what that personally means to you.
Well, "restoration" is to restore it. When I say the "Restoration of an American Idol," I believe that I'm bringing back being yourself into hip-hop music. I believe that I'm bring back not having to feel accepted and not so much caring about what people critically think. Just bringing back being yourself in hip-hop. Bringing back being different. Making that OK again. That's kind of how I feel about what I'm doing and about the project as a whole. It's the first time I talk as just myself.
Talk about the transition period between Broad Shoulders and Restoration, where you kind of became more confident about the work that you were putting out, and just taking ownership and more control of the creativity and the process.
I think that something that might be different, and maybe it's not different about me, I have a lot of -- I guess I would call them -- famous friends now. Most of them found me through my music. There's really not a difference. Lil Wayne told me he liked "Speed Racer," to any of my fans that come up to me in the middle of the street and say "yo." It's all the same thing. I think that my fans really know, the notoriety, the blogs, the stories that I hear helping people throughout situations through my music, that is what made me more confident in myself. That is what made me believe in myself. I think the expectations my fans have for me to be the best I could possibly be is what pushes me to be a great every day.
How do you combat writer's block?
I get writer's block usually right after I put out a project. I had writer's block just until the day I made this album. It’s just a rough song, it’s a bridge, it’s a chorus. I always get that because everything I do -- you never move backwards, you always move forward. It always has to be one step better. When I put out a project like Restoration of an American Idol, it's so good where I have to do something better than that. So then I have writer's block, because I have to write something better than that. I keep constantly going back and going back, and that lasts for a while. I think it's been about a month and a half since the project has dropped. It wasn't until right before the day I left to go on tour I got my writing back and my confidence back. This tour is my first headlining tour. I'm getting to meet and go places to my fans that I've never seen before. To hear your fans -- your project just dropped a month ago -- screaming the words, like knowing that shit, that puts so much confidence into you. You feel like you're the shit. My mother tells me three things: be yourself, be sober, and be humble, and you'll be good. So I'm going to keep getting to it.
You're very comfortable with being yourself, based on your music. What moved you to let the world know that you are bisexual earlier this year?
I think that it wasn't the world -- it was my fans. It wasn't for any media, it wasn't for anybody or any blogs or anything like that. I put it out there [on Twitter] for the fans because it was the day before my birthday -- I was about to be 21 -- and I just had certain points in time where I felt like I'm black, I'm a rapper -- there's a persona. You don't want to do anything that makes your fans not like you anymore, but I realized, 'F--- it! Be yourself.' You got to be yourself. That's what I said; that's what my parents have always told me. The only people I felt like I deserved to tell was my fans because if your fans don't know you, how can they support you?
Then there was also the idea that for somebody that has a platform like mine that can speak to these many people, to come out and say something like that, I hope, puts courage in people to do the same thing. I always say the biggest dream I've ever wanted to accomplish is, in I don't know how many years, hundreds and hundreds and thousands of people at a sold-out show, and I just tell them all to look at each other, and they look at their sides and see that there's black, white, gay, straight, rich, poor people all around them and just realize they're all here for music and that there's nothing different. I think that's the power music can have. Just reminding people that we're all human at the end of the day.
Do you feel like every song or project that you put out always has to be a deeper message?
I like to think about my music not as songs, but as memories. As a sophomore in high school, I had this great African-American history teacher who asked me, "Do you think that hip-hop rappers have a duty to their community to make and change and say positive things?" And I said, "No," because I felt like, at that point in time, as a rapper, you have the freedom to say whatever you want to say. People will listen to whatever they want to listen to. You are your own person and you should never change that aspect of who you are based off of what someone else wants to hear. I still feel like that. With my morals and my values from my parents, I always want to do positive things -- that's how it's always been taught to me, whether it's helping out homeless youth in Chicago or any of those things. When you have time, when you can do something, do it.
Fans have been petitioning for your brother to run for mayor in the city. Would you ever consider a position of office in Chicago?
Possibly. My dad's a politician. We do community work, so I mean possibly.
You've accomplished so much in your flourishing career, but was there ever a hurdle that almost stopped you from potentially pursuing music?
Yeah, it happens all the time. It's not just one thing. There's multiple times where things happen in life and you feel like you're against a brick wall and it's always easier to sit back down, and Chance has a line like that. It's way harder to stand up on your own two, but I think that the reason why I am where I am today is because I haven't given up. If I did, none of this would be happening. It's hard being an artist, being somebody that people expect so much from, going places, trying to be yourself and also trying to be respectful. I’m still a kid. I do these things for my fans. I do these things for my music and my career.
You shouted out Kyle yesterday, who you've collaborated with and consider a friend. He has the No. 1 song on the Top Rap Songs chart. With No. 1s, Grammys, VMAs, trophies, where do you stand on those types of accolades?
I think they're great accomplishments. That's not really how I think I measure my success. I think I measure my success by fans and what they say. I get write-ups all the time -- some people don't like certain things.
What do they not like?
I had this guy write this crazy article about me the other day. I had this show in Milwaukee that we sold out, and the guy stood in the crowd and wrote this whole article that was like, "If Taylor Bennett wants to step out of Chance the Rapper's shadow, he's going to have to do a lot more." I had a Nike show right before I went there, so I got there about 10 or 15 minutes late, but I still stretched the show out. But he just wrote all types of crazy shit. My voice was gone so I ended up playing MP3s. I mean, I still had my vocals on but show tracks, that's how it goes -- so he writes an article saying that I lip-synced the entire time.
I don’t know if you’ve ever heard the line from Kanye West where he said he's going through Instagram comments to boost [his] confidence. A lot of people don't realize but rappers read articles. When we get hit hard, you gotta take it and move on. I read that shit, I was like, nah, that's some bullshit. I didn't say anything about it or bring any attention to it. I just stopped, went to the studio, made some new show tracks. I've been working on my vocals and stuff like that. Now we're doing our thing. Everyone won’t like you, you can't make everyone like you. You can always try to be the best person you can.
Do you ever feel like you're in your brother's shadow even though you're both successful in your careers?
I realized this a long time ago -- I will always be his little brother. I can be more famous than Chance and I’ll still be his little brother. I think it's pretty corny [being constantly called] Chance the Rapper's younger brother. I get it, dude! You're a journalist, you do write-ups for hits and retweets or whatever. The more people that are attracted to [the story], a.k.a. throwing out somebody’s bigger name to bring out people to go there, it makes sense. But then after a while, when you know a rapper for so long, I'm pretty sure there's not anybody new that doesn't know Chance has a brother so now it's like, what's the leverage? What does that really bring?
My thing is me and brother are super close so I don't really care what a lot of people have to say, but I do think that when they say that, sometimes it cuts me short. It's like, "I don't want to listen to this. Dude is only doing this because of his brother," and those are all people who haven't heard my music. You can not like talent, but if somebody’s talented, you can tell. He may not be your favorite basketball player, but you still know his three-point shot. I don’t think it’s so much pressure, it’s more about just the consistency of it, so that’s why you gotta talk to people who not just like your music, but like music.