Photo by Evan Brown (@actuallyondirt); Styling by Luis Cruz


Taylor Bennett Is Coming Up And Making A Name For Himself

With a little support from his big bro, of course

It's almost too easy to compare Taylor Bennett to his older brother, Chance the Rapper; their similarities include their features, pedigree, passion, and profession. They also possess the same playful and positive energy that makes them both so likable. But now, Taylor is coming into his own and making it easier than ever to tell the difference between the two. Sure, Taylor still shares his older brother's inherent effervescence, but he is also revealing more and more intimate details about his complex life experiences that are all his own. It's possible to hear this on Taylor's debut album, Broad Shoulders, and in his latest single, "New York Nights," featuring Stro and Jordan Bratton; Taylor talks about everything from his serious medical problems (he was rushed to the hospital and diagnosed with a blood clot in his left lung in late 2015) to dealing with the arrests and deaths of those close to him. And as recently as last night, Taylor revealed on Twitter that's he's bisexual, a candid and powerful statement, especially in a world which has very specific ideas of what black male sexuality is meant to be.

As he's risen to new heights of fame, Taylor has turned to different sources for comfort and inspiration. Along with a renewed faith in God, Taylor points to Bob Marley as a major influence.

"Bob Marley never knew what his dreams could possibly be because he was never about 'possibly' doing things. If he wanted to do something, and he knew it was going to mean something to the world, he did it," Taylor says. "That's kinda how I want to see my art as a musician in everything that I do."

Taylor loves every aspect of being an artist from the interviews and photos with fans to the trolls on social media. "I love people talking shit about me on Twitter," he says with a smile. "I'll be like, 'Aww, you care about me enough to say this shit, alright, fuck you, bro.' Seriously, though, I love it. It's my dream, it's what I've always wanted to do, so I'm just very proud to be doing it."

Now that Taylor is done touring with R&B sensation Tory Lanez, he's taking the spotlight at his own shows. Last month, the 21-year-old performed in front of a sold-out crowd for his headlining show at the Metro in Chicago. Get to know the other Bennett brother before he levels up in the gallery, below. Also be sure to keep an eye out for his next EP, which will be dropping sometime in February.

Photo by Evan Brown (@actuallyondirt); Styling by Luis Cruz

What kind of music did you grow up around?

I grew up listening to a lot of different music. I had my whole scene/alternative phase and listened to Death Cab for Cutie, As Tall as Lions, Nickasaur, Nevershoutnever... so many different people. Then I had my The Smiths period; I listened to Queen a lot, and, of course, The Beatles. I had a really deep love for Regina Spektor, Joanna Newsom, Erykah Badu, and then I've always obviously been a huge hip-hop fan as well, so Kanye West and Lupe Fiasco. Twista is the reason why I started making music in the first place, and I was really into Flobots for a while. I grew up listening to Coldplay, Lenny Kravitz, Maxwell, Seal, John Legend... We listened to Outkast a lot and obviously Michael Jackson and the Jackson 5. I used to like Frankie Lymon a lot and I love Mr Hudson. Just a lot of great music. I'm really into Frank Ocean right now. I love all his new stuff. I listen to a lot of Chicago music nowadays that I'm just older, like Smino, Saba, Saba Pivot, Superboy, and Morocco Brown—that's my artist, I listen to his music and his new tape like I'mma die for it 'cause I just really like it.

I read in another interview that you started rapping and freestyling when you were in the fourth grade. When were you at the point where you were like, "This is definitely what I want to do as my career for real?"

When I was nine, I heard a Twista song called "Hope" featuring Faith Evans with the chorus "Cause I'm hopeful, yes I am, hopeful for today, take this music and use it, let it take you away." I remember seeing Twista rap on the TV, him being from the west side of Chicago, me being on the south side, and just knowing nothing is certain. There are so many possibilities in the world, but if you take advantage of the opportunities that are given to you, then you can always persevere through the rough times. At that point, I was like, "I wanna be a rapper," but I didn't know that I wasn't gonna go to college 'cause that's a huge thing for my parents. [They were] like, "Well, you gotta be educated, you gotta have a degree, you gotta have something to show."

I know my dad always says this—I think he actually got it from [Barack] Obama because they're really good friends—"The best rapper in the world is not the top rapper right now. The best basketball player in the world is not the top basketball player right now. The best rapper in the world is in his mom's basement thinking about how he's going to write, and how he's going to do." You only get so many chances, and if you don't do the right thing at the right moment at the right time, it just won't work out for you. So it's all about hard work, and it's all about effort. You can sustain a living off of just making music, and you don't have to be the biggest artist in the world, you can live off your income. When I realized that, I was a senior in high school, and I remember telling my parents, "I don't want to go to school, this is what I love to do." At first, my parents were like, "What? Your brother's already a rapper, that's already one kid that's not going to school." Nothing in hip-hop is for sure; you can be the biggest artist that you can, but the next day something could happen, and in a snap, it's gone, so they really didn't want me to do it at first. Then we all had the same mutual understanding, that nobody wants to wake up at 35, 42, 53 and look back at the world and say, "What if?"

Photo by Evan Brown (@actuallyondirt); Styling by Luis Cruz

I'm sure that's kind of crazy for your parents to have both of their kids end up becoming rappers.

I'm sure it is, but they love it now. [My parents] both worked in politics, so all their friends whose kids were [Chance's] age were like, "Oh yeah, my son is going to Yale," and, "He just got accepted to this Ivy League school. What does your son do?" My mom was like, "Well, you know, he's looking at options for school." I remember one day my dad just told her, "Say he's a rapper. Say your son is a rapper. Say that's what he does." My mom started doing that, and now all those kids that go to Yale and go to Harvard [and their parents] are like, "Can you get us tickets to Taylor's and Chance's show?" So it's funny how things work out. I'm very very blessed, for sure.

Given that your parents both work in politics, and growing up around that, how would you say it's been beneficial for you to be informed about what's going on with the world, and why is that important to you?

It's definitely important to always just be informed about what's going on in the world, no matter if it's politics or war. Whatever it possibly may be. I like to think that I got to see a different side of it, too, because growing up on the south side of Chicago in the hood, I have a lot of friends that are in jail. I have friends that just got out of jail. I got friends that are dead now. I saw multiple perspectives of what it's like to have money and to not have money. I lived on the north side afterward, so I found out what it's like to have white friends. My brother was blowin' up while I was in high school, so all these rich kids wanted to hang out with me, and I saw what it was like. I saw the values, and I saw the respect values, and I saw how they treat their parents and how they treat their friends versus kids that have nothing and how they care so much for their family because, at the end of the day, that's the only thing that has their back. I try to reflect that in my music a lot. What I always like to say is that we were never poor or broke—we were always lower class. We might be middle class now—if that's even still a thing since Donald Trump is our president—but I've seen a lot. And my parents have always been smart, hard workers. I think me and my brother get a lot of that from them for sure, about always making sure that no matter what at the end of the day you can take something away from every experience, and you can always make sure that everything that you do works out positively and beneficially for you.

What has it been like just being a part of the creative community in Chicago?

When I was younger, and I would be doing slam poetry competitions or I'd go out of town and I'd just started making music and I'd be talking to record labels or whatever, people would always say—and they still say—"What's going on in Chicago that makes this music so different?" I'd always say, "We die in Chicago." I have a lot of friends that have passed away, there's a lot of pain in Chicago. There's a lot of hunger in Chicago. When I was growing up, I had friends that were friends with Chief Keef and a lot of those people I went to school with were friends with King Louie—that's kind of like my big cousin, I grew up with him. It's the perspective and the dream, and the idea is so close. When you know people that are in the family, and you see Chief Keef pullin' up—I mean before he was banned from Chicago—in all these expensive cars and all these things and you realize and you say, "I lived that life too. It's not that hard for me to become a rapper." I mean, who can deny trying to be that? I think that it's a lot the same with me and my brother and all these people that know us. We're very predominant faces in Chicago, so a lot of people see us, and I think there's a hunger that is there for it. People understand that it's not just one person—all our stories are different, but we all come from the same city, and we know that we're all very very talented. I think that a lot of that hardship and a lot of that pain fuels the creativity that we have.

I was just talking about it the other day, I remember when Chief Keef first came out, and then there was Lil Durk, KD Got Bandz, Sasha Go Hard, and all these different people that were kind of came from the drill scene of Chicago, and people were like, "Oh my god, this is a crazy-ass wave of people." But that's over for Chicago—don't nobody want to hear that drill shit no more. And then all of a sudden there goes Chance the Rapper, Vic Mensa, Alex Wiley, Mick Jenkins, and then people are like, "Aight, well that's over, don't nobody want to hear that shit no more." And then all of a sudden you got Sabas and Taylor Bennett and Superboys and all types of people. And they're like, "Aight, that shit's over, we don't hear that shit no more" and then they're like, "Oh shit, you got Lud Foe and Young Pappy..." There are all these amazing artists and really talented people, and it just keeps happening because the thing that a lot of people fail to notice is that nothing in Chicago has really changed. Still, kids dying every day. I just lost a friend, one of my friends just got out of jail yesterday that I would consider my little brother, that's younger than me. Just because we makin' music and just because it's now become something that's absorbed attention doesn't mean that it's changing.

Photo by Evan Brown (@actuallyondirt); Styling by Luis Cruz

Let's talk about style for a little bit, cause I've been looking at your bling here. I'm also really into this jacket.

Thank you. Diesel just started sponsoring me, I just did an ad for them. I've been doing my model thing for a lil second. We did a shoot with them a while ago, and they've been sending me a lot of clothes. I'm also sponsored by Foot Action, so I do a lot of modeling. I really like modeling. I really like clothes.

How does one learn how to model, do you have to practice, do you have a coach, how have you fallen into it?

When I first started doing it, [I had to learn that] every shot is not the coolest shot that you're possibly gonna have. I had to start stepping back and being like, "Well, I'm gonna put my hand on my arm, and I'm gonna do this shit and I'm gonna do that shit." Anybody can edit a picture, but can you make yourself look cool? Now when somebody pulls up and they're like, "I got a camera" I just instantly do... I call it my Drake pose. I'll show it to you later. I think it's very Drake-ish.

Yeah, I've been going through it with Drake, he used to be one of my faves and I don't know, I'm feeling very conflicted with him.

It's like, "Damn Jimmy, what did you do?"

Just the fact that Views even got nominated for a Grammy...

Nooooo. But you wanna know something about


? I still don't really like it that much, but I fuck with Drake, though. He's a very great person, he's a very genuine guy. I've met him a couple times, he's an amazing artist. 


kind of changed perspective for me of Drake, but I do like that one song [with the line], "Life is more than sleeping in and getting high with you." I love that shit. That's my shit.

Yeah, "Feel No Ways" is fire.

I actually recently just got onto it. I will play it every time I get in the car.

Photo by Evan Brown (@actuallyondirt); Styling by Nina Kallas

Going back to politics, what are you going to miss the most about the Obamas being in the White House?

Oh man, 'cause I've been in the White House—we've been so many times. I'm great friends with all of them—Malia, Sasha, O-Beezy [Barack], and Michelle. They're all great people, and I've known them since I was a kid. There is a character about them that, either in or outside of the White House, you can tell they're a very, very concrete, together, family. Everything they go through, they persevere through it together. I think what I'm going to miss the most from the Obamas is the presence of a concrete, together family. They're the perfect representation of what anybody wants to be in a family, and the morals and the things that they stand for are exactly what I want my family to look like and what we strive to look like as well as anyone else in America. I think that I'm going to miss the presence of that American family—two little girls, two adults taking care of them... You got Malia going to an Ivy League school, Sasha's been doing her thing—she's a very brilliant person as well, and just seeing them together just makes everybody smile. So I'll miss the family presence in a way, for sure. They're amazing. I love them so much, they're all great people.

What was one of the major highlights in 2016 for you? 

Sometimes, I feel like this very often, that God tests me. You know when everything is going wrong that there's something that's about to come up that's way better. I remember going through this whole situation and just saying, "Man, I'm out here, this is SOBs, I've got to sell this shit out. I'm from Chicago, this is a huge fucking deal." I think it was like the last song we did was not rehearsed, we just played it, and I remember just feeling like, "This right here is why I make music. This right here is why I do what I do." Feeling like I had been tested, but being like, "Thank you, God, for fucking with me right now because you gave me the strength, you gave me the power, you brought all these people here that know nothing about me." Chance is my older brother, and I've become more of a concrete artist since

Broad Shoulders

and these things have been out, but that was the first time that I realized that everybody in the crowd knew the words. That was the first time that I realized that nobody came up to me and said anything about my brother. That was the first time that I realized that as an artist, I finally stood on my own two feet after all these years. That was definitely a very, very, very important moment for me in 2016.

So 2017 is gonna be dropping the album, you're gonna be doing more shows...

Dropping the album, we're gonna be doing way more shows, it's gonna be a really big year. We've got a lot of big shit going on. Hopefully,


stops being so fucking petty and puts me on the Freshmen List. No, I'm just playin'. So yeah, we have a new project coming out, and we've got a lot of big features on there, there's a new song with Chance and Jeremih does the chorus, and Mike Will Made It produced it. There's a song with Lil Yachty on there, SuperDuperKyle is on there, we got my boy Raury on there, it's all types of people. So it's gonna be a really good song. I'm working on a new track with Kehlani right now, so yeah, it's just a really really good project. I'm really happy.