A Conversation with Taylor Bennett about Self-Love, Faith and Making his City Proud

Coming off the recent success of his latest album, Restoration Of An American Idol, Chicago artist Taylor Bennett wasted no time before jumping right into his first headlining tour “The Taylor Bennett Show” — which sold out and came to a close at the end of April. The Chicago rapper is no stranger to hard work though. Bennett released his critically acclaimed project Broad Shoulders in 2015, racking up millions of plays across streaming platforms and catapulting him into the national conversation of rappers to watch. A year and change later, Bennett has gone the distance, honing in on his writing skills and turning his music into a lifestyle for his fans.

After a few lessons learned and a growing collection of music to his name, Bennett is in a place today of personal freedom and Restoration Of An American Idol is a clear reflection of that. The project has naturally become a soundtrack for any young person on the brink of finding themselves. Bennett’s latest music is a genuine culmination of his experiences, ones that are fleeting and some that have stuck with him. From childhood stories and relationship tales, to light-hearted anthems that lift your spirits upon first listen, Restoration Of An American Idol is a warm and infectious body of work, with clever wordplay that features Bennett sharper than ever. The album includes a nostalgic collaboration titled “Grown up Fairy Tales” with Bennett’s brother, Chance the Rapper, which serves as the project’s leading coming of age story. You’ll also find features from friends and peers like Raury, Jeremih, Supa Bwe, and more — who all match the album’s vibrant sound.

Throughout Bennett’s journey in the music industry, he’s managed to remain independent and in control of his creative process. It’s evident that the 21-year-old rapper lives and breathes his music and for any hip-hop fan, that’s gratifying to watch. It’s also worth noting that the Chicago rapper is more likely to acknowledge his team and city before his own accomplishments, which isn’t too hard to recognize in our first interview together.

Get to know Taylor Bennett for yourself below.

Charlie: How’s tour life treating you? Do you have any memorable moments so far that have stuck with you?

Taylor Bennett: Tour life is awesome man — I’m feeling great and very accomplished. I’m an independent artist, I funded my own tour, and I’m very appreciative of my awesome team. I didn’t know how big the tour bus really was until it pulled into my driveway back in Chicago. It’s my first headlining tour. The first tour I did with Tory Lanez was just a small team of four people. Now I got a full tour bus, plus a van with my Chicago family on the road.

The first stop was definitely very memorable. Boston was my first stop on the tour, but it was also the first show to sell out. I had the awesome experience of checking out The Phoenix S.K. Club — a lot of history in that building. Felt like a college kid for a day. Ton of fun!

What were some of the themes you wanted to explore on Restoration Of An American Idol?

This project is the most “Me” my fans have ever seen of me. I wanted to explore courage within the project. I wanted to express to my fans and new listeners that it’s okay and empowering to be yourself. I make hip-hop, and hip-hop to me has always been about being yourself. The music and production was hand selected, which varied from my last album where one producer produced the entire sound of the album.

One of the biggest jumps I noticed in your career was creating a really cohesive project with Broad Shoulders, and I think some of that had to do with you pairing up with producer Ludlow. How did you guys get together?

Ludlow that’s my guy! We spent a very long year creating Broad Shoulders and it was awesome to have someone so focused on my music. Previously, I was working with engineers that were worried about so many different sounds from different projects and artists. Ludlow, for the most part, was pretty exclusive to my project and we attended to every detail together leading up to the release.

I met Ludlow at a festival in Chicago a few years back and reconnected with him a few years later through our management teams.

With a lot of your projects — especially Broad Shoulders, you made a conscious effort to include lesser known Chicago artists. How important is it for you to continue to highlight and put on other artists from your area?

Broad Shoulders was about an original sound — I wanted original voices. I hand picked the featured artists on that project and we knew the sound that we were looking for. We weren’t chasing big names but big sound!

I think it’s very important to connect with the peers and artists in your community who are trying to dig into the industry because when I first started I wanted everyone to give me a chance. I also wanted to steer clear of the clearance issues huge labels often give. At the time when I was working on the project, I was very limited in money and I didn’t want to make the clearance process an expense.

taylor bennett
Taylor Bennett in San Francisco, CA at Brick & Mortar – Photos by Colin Hoefle for REHAB

What would you say is the biggest difference between Broad Shoulders and Restoration Of An American Idol?

The biggest difference to me is the perspective I’m writing in. I was writing Broad Shoulders from the perspective of many different people who were involved, whereas in my latest album, Restoration of an American Idol, all the songs were written from my perspective.

How have recent experiences and personal obstacles helped you transcend in the last year or two to the place that you’re currently at musically and personally?

Growing up I always wanted to rap and I wanted to follow my dreams. I see a lot of my friends chasing theirs and I’m reaching mine and want to inspire others to reach theirs. A lot of people don’t get the opportunities I do, so I have to be true to myself, focused, and non-selfish to those who have always supported me. Chicago has always had my back so I’m fighting for it everyday. I’m currently working to help fight the homeless youth crisis through many initiatives starting with my hometown.

Who were your music idols when you were younger? Is there any music or artist that you’re currently inspired by?

I currently can’t stop bumping the new Kendrick — that s*** is straight fire. The amount of doors that my brother Chance is opening for independent musicians is undeniable, there’s no way I cannot be inspired by that. Growing up I used to listen to Lenny Kravitz, Aretha Franklin, Queen, John Legend, Kanye West, Outkast and more. I love all types of music.

I just heard “Only Brother” the other day and having a brother myself, it had a lasting effect on me. What adjectives would you use to describe your relationship with your brother?

Unbreakable & Unequaled.

You’ve explored faith and God in the past, like in “God’s Children” from your first mixtape. How has your faith evolved over time and played a role in your life?

I believe that my talent is God-given. I count my blessings on a daily basis and I’m very open about my faith.

You took a really courageous step this year when you opened up about your sexuality. You mentioned that it was the silence from some of friends that really spoke volumes. If you had the chance, what advice would you give to someone who is struggling in some way or another to be their true selves?

I would just have to say to them that it’s the best thing they could do for themselves. There’s no need to live in constant fear. We all need to stand together. Love yourself!

So what’s next on the agenda for Taylor Bennett? 

I have a really big music video coming out the third week of June. It’s the first off of the new project — be on the look out 😉


Feature Photo by Evan Brown
Stay Connected: Instagram | Twitter | Soundcloud | iTunes

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Charlie Ranahan

Charlie Ranahan is an Oakland-based writer and aux-cord connoisseur who spends his free time trying to make Ecko Unlimited cool again.