Exclusive | Entertainment
Taylor Bennett. Hometown Hero. Creative Force. Artist.
Taylor Bennett is so much more than the younger brother of the Grammy Award winning artist Chance the Rapper. One can liken Bennett as a parallel to Chance, similar in style and upbringing yet in their own respective lanes. Bennett is forging his own path, following his passion with a trajectory that can only be measured by his own standards.
Seven years ago, Bennett came out as bisexual to the world, in true Millennial fashion, through a tweet. Immediately after, he ignited his “Be Yourself” campaign, which can be described as an embodiment of vulnerability and the embrace of one’s true self.
Make no mistake, Bennett is an artist, producer, manager, entrepreneur, father, and LGBTQ+ advocate. He’s as multi-hyphenated as they come.
In his latest era, he delves into the history of music, tracing the roots of genres like R&B, hip-hop, and house back to Black culture. For example, Gayes did you know that Frankie Knuckles, a Black, gay man was the creator of house music…a genre born and bred in Chicago?
He makes those implicit connections to channel the homegrown juke sound of Chicago that he grew up with. However, it’s much more than a rediscovery of music; it’s a movement, it’s an amplification of what once was and hopefully what can be. Bennett aims to expand the musical palate of Chicago beyond drill and hip-hop, embracing the entire spectrum of Chicago’s iconic music scene.
Coming off the heels of “Coming of Age”, where Bennett traverses through rap, R&B, and punk, he is now in a phase of artistic exploration. In his journey, he finds himself circling back to his rap roots.
In his latest single “2 Much”, alongside Chicago legend King Louie and Lala 2Muchh, Bennett more than proves his rap chops in the juke-inspired anthem.
In this Gaye Magazine exclusive sit down with the “Be Yourself” rapper, Taylor Bennett discusses what inspired him to explore a new sound, how he hopes to expand the Chicago music scene, and his journey as a bisexual figure in hip hop.
If I’m walking on the street and I tell someone they need to listen to Taylor Bennett right now, what’s the first song you recommend they listen to?
“…My three contenders. First, ‘Broad Shoulders’, secondly ‘Be Yourself’, and if you’re in Chicago, ‘2 Much!’”
So we’re just coming off of Pride Month. Did you do anything? Did you have any fun?
“What’s funny this year, I actually spent Pride a little different. I went to Everyday People in Chicago during Pride. I missed last year’s Chicago Pride, but I made every year of Pride since I was 14 in Chicago. Now that I’ve been to different cities and performed at their Prides, it’s different man.”
“Everybody comes out of Chicago. It’s like this big ass crazy party throughout the city. Primarily, in Boys Town, the North side of Chicago, where they have this big ass parade. Also, on the South Side and on the West Side, there’s all types of shit. Everything from day parties to club events to bar hopping, like Chicago goes hard.”
In your latest single, “2 Much”, you rap unnaturally fast during your verse, how did you not get tongue tied?
“My first love is hip hop. The first artist that I ever felt inspired to make hip hop and rap music from was Twista, and he’s from the West Side of Chicago. He had this song with Faith Evans called ‘Hopeful’.”
“[At the time], I was living on the South Side [at] 10 years old. It just resonated with me a lot because he talked about the idea of not making it back home or just like the struggles of just living life.”
“It wasn’t glamorizing all the hip hop materialistic shit, that I love, but was used to hearing. From that point, I was inspired by Twista to challenge myself, not just as a writer, but as a rapper.”
“A lot of my very early music is really fast raps. Like the first write up I ever got was this fast rapping song called Speed Racer. And it kind of became a knack of mine.”
Can you talk about the importance of juke to Chicago, with emphasis on house music being started by Frankie Knuckles, a Black, gay man.
“A lot of people don’t know this. Frankie Knuckles actually came from New York and when he was in New York, he would spin at a lot of different gay clubs.”
“So there’s a lot of origins of house music that you’ll see in our community at the clubs or you’ll see at house music parties and events. The kickbacks, the juke parties, all of those different spaces allowed Black people to come together and have self-expression. It’s the foundation of our communities and how a lot of us met each other and how a lot of us know each other.”
“Some different sets of dance crews have or had affiliation to gangs. There was a point in time, where a lot of these folks that decided to clique up as dance crews would push off of this street shit, so that they could literally battle people over their issues.”
“That’s something that Chicago needs right now, but it’s not something that people are focused on. I think there’s such a significance of Frankie Knuckles bringing that style of music to Chicago and us holding on to it.”
“Eventually, we got to this space in Chicago where we had a genre of music that was created by us and for us.”
What was that experience like co-directing the “2Much” video with legendary Chicago figure D-Gainz?
“Again, the whole purpose of doing this project was to bring Chicago together and bridge these different gaps, and when I was growing up in Chicago, D Gainz was like legendary because he broke all the biggest Chicago artists…Chief Keef, Lil Durk, King Louie, Sasha Go Hard…the list goes on.”
“When I was a kid, I always wanted to get music videos from him, but I didn’t have enough money. I was just starting my career off. Also, at that point in time, I think what DGainz was working on and the folks he was working with, even though a lot of them were my homies, were pushing a bit different of a message than what I was saying and what I was rapping about.”
“So fast forward all these years later, I ended up having a track with King Louie and also have this juke track and we’re trying to figure out who we want to shoot it and who we want to direct it and capture it. Shoutout to my creative director, Forever Band, he was like ‘you should get D Gainz to shoot the video. I feel like he would be down’.”
“Honestly, when he first said it, I was like I don’t know, because I know what DGainz shoots…I know what I want this video to be. [However], it was actually the best recommendation, because DGainz is also a Chicago kid. So even if it wasn’t something that he had captured or put out before, it was nostalgic and purposeful to him.”
“So working with him on this was super dope, because I got to see him do things that he told me [he’d never done before]. That’s what made it cool too knowing that an idea that I had, and I’m not a director, was now pushing him as a director to advance his vision was dope.
Was this your first time ever directing a music video?
“This was my first time directing, I think to this extent for sure. There’s been other videos that I’ve worked with, but the difference with this shoot is, it was very strategic. So like the party scenes in the video are actually on my birthday. Like that’s my real birthday. I threw a party called the biggest juke party for my birthday.”
“I told everyone it was going to be a video shoot, and we packed it out with a 1000 people, and we just threw a big ass juke party and we marketed the song at the party and beforehand with different influencers. So by the time we did the video, everybody was like oh shit, not only am I in the video, but I know the words and now I’m super hyped for it to come out.”
“It’s always been a purpose of mine as well to show rap music on a high caliber level and scale, which I think people aren’t really used to seeing.”
In the current music scene, do you feel like a lot of rap is like “fast food”, quick and rushed?
“I think we’re in a commoditized era right now, so I think everybody wants to be entertained. I think there is a need to feed the masses. I feel like from a label standpoint, music wise, I do think there’s a lot of people at labels that are like I don’t know what to do right now, I don’t know how to sell a record, but what I do know is I have this money.”
“I think that’s a big thing on why I never signed a deal, because I think a lot of times, the label gives you an advance, or they pay you money. They’re not paying you, so they can help you, because they know the perfect strategy and formula to blow you up to the biggest. They’re usually paying you because they see that you have money that’s coming in. They might have a few connections to [elevate] what you’re doing, but they’re not going to come write a song for you.”
“So I feel like, again, there’s a lot of labels out now that are looking at Tik Tok, looking at Instagram, looking at YouTube, trying to figure out how to find and buy the new sound.”
“I think the industry is having trouble trying to figure it out right now, but I don’t think that we as people should be looking at the industry as much as we do. I think it’d be great to get back a little bit more to underground artists and supporting up and rising artists and really seeing the success through their journeys. That’s how I got on…it’s not a lot of that anymore.”
How do you juggle fatherhood while maintaining a music career?
“I would just say balance. That’s my biggest thing. Balance. I have three children, I have my own career, I manage my brother…”
“I have my partner. When we’re together, we still have to love each other. On top of that, of course I’m me, so whenever I go outside someone is like hey what’s up!”.
“The key to all of it is balance. Do things that you’ll be proud of and do things that you enjoy and live life.”
When you came out as bisexual in 2017, do you feel like that moment was for yourself or for others?
“I think I go back and forth. Sometimes, it feels more beneficial for myself, because outside of me being an artist, I’m a person. There’s a comfort and a respect for myself that I find in that, especially seeing, not just men but people in general will never have the comfort or satisfaction of being present.”
“How I feel about it is I don’t have any secrets. I’ll say this, I’m bisexual. So a lot of people whether they’re gay or straight, they just don’t believe bisexual is an option or is an existing preference.”
“I always felt like it was funny, because I feel like there are a lot of straight people that say you can’t be bi, you can just be gay. Then again, I know a few gay people that are also like, you can’t be bi, you’re just gay."
“Another thing is right after I came out as openly bisexual, the next year I had my son. I never had a public relationship or anything the world would know about."
What was your mindset like before you came out?
“There’s a clarity in being open and being who I am. I don’t know how to describe that cloud [before I came out], because I’m so far away from it or it’s something I never saw before it was gone.
“But when I came out as bisexual…there was a confidence boost in a lot of different spaces of my life but I think one of the most was in my subconscious and how I felt about myself and the respect that I had for myself.”
“I knew what I said, but I didn’t know how people were going to react to it. I think the respect that I got from who I am, makes me respect myself more every day.”
As a rapper and storyteller, Taylor Bennett seeks to revolutionize the soundscape of modern day Chicago through his artistry. With “2 Much” being the latest example, Bennett actively incorporates his own personal experiences and music history knowledge to bridge a gap he feels is sorely needed in his hometown.
To the average outside listener, it’s easy to distill the Chicago music scene to simply drill & hip hop, but it’s so much more. The sounds of The Windy City imbue soul, queerness, and a palpable rawness. In short, Chicago has range, and Taylor Bennett personifies that fact as a leading independent queer artist.
…Gayes make sure to put “2 Much” on your party playlist, you’re going to need it!
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