Finding Your Sound: Taylor Bennett
The Chicago rapper on footwork, defying expectations as a Black artist and what his coming out experience has meant for others.
by Juan Navarro
In the ever-evolving landscape of hip-hop, few artists embody the spirit of artistic freedom quite like Taylor Bennett. The Chicago native has been steadily crafting his own lane, one that defies genre constraints and challenges preconceptions about what a Black artist can create. In a candid conversation with TIDAL, Bennett opened up about his sonic evolution, the power of independence and the importance of authentic self-expression.
“I’ll never forget, I was in the studio working on ‘Good Guy’ with Dj Verner, Zxxk and DEX LVL,” Bennett recalls, describing the genesis of his genre-bending sound. “Being Black in America, I think it makes you feel in a lot of ways that there’s one certain thing that’s expected, especially when it comes to entertainment and the different perceptions we see on TV.” That day became a turning point. “I took my shirt off, got two bottles of champagne and was literally like, ‘I want to make rock songs.’” His recent work has seamlessly blended pop-punk and pop-rock elements, drawing inspiration from artists like Matt and Kim, Lupe Fiasco and Plain White T’s. It’s a bold direction for a hip-hop artist, but Bennett sees it as a natural evolution. “The world is yours to explore … I think the limitations a lot of times are set by opinions and what you feel you’re expected to do.”
While Bennett’s musical explorations have taken him through various genres, his latest single, “The Return,” marks a confident homecoming to his rap roots. “I genuinely believe I’m one of the greatest rappers,” he states with conviction. “I’ve always had the bars, I’ve always had the raps, but now I have everything that I need to do what I need to do, and do it in the right fashion.” He cites JAY-Z as an inspiration, not just for his artistry but for “how he’s gone about trying to sustain a space in hip-hop without deviating from who he is and also the business … picking the right opening acts, having the right distributors, getting the right deals.” This return to rap isn’t just about proving a point — it’s about creating positive, diverse hip-hop that reflects the full spectrum of Black community experiences.
Bennett’s connection to Chicago runs deep. It’s particularly evident in a recent single with Tha Pope called “Get Loose,” which embraces the city’s footwork culture. His Sunday studio sessions have become a hub for local talent, fostering a competitive yet collaborative environment. “We had six producers at a time in a studio with three rooms, so different songs were being produced in all these different spaces,” he explains. These sessions produced tracks like “2 Much,” with King Louie and Lala2Muchhh. Despite not being a natural dancer himself, Bennett has immersed himself in the footwork scene, learning from legendary crews like Creation and Prophecy. “How could I create footworking music and not myself dive into the culture of it and try to learn it, even if I look stupid?” he reflects. “It’s about showcasing all the cultural elements of Chicago, not just what people typically expect.”
In 2017, Bennett came out as bisexual, a decision that has profoundly influenced his artistry and connection with fans. “Coming out was an amazing thing for me,” he reflects. “I understand my representation for the world, and there’s people out there that, based off the fact that I did come out and I’m freely still within myself … builds up this ideal and comfortability in being whoever you want to be.” His “Be Yourself” series has become a powerful vehicle for personal growth and self-expression. “While ‘The Return’ was considered for part four, we kept the series distinct,” he explains. “Each installment explores different facets of self-expression, with part three being a Chicago love letter.”
Bennett’s independent journey was shaped by early experiences building his brother Chance the Rapper’s career. “Me, Chance and my dad got together in our kitchen,” he recalls. They pressed hundreds of burned CDs of Chance’s 10 Day mixtape, hand-delivering them to high schools across Chicago. This grassroots approach has become a blueprint for artistic freedom in the streaming era. “There’s so much money out here to be made, and I don’t think enough artists really understand … What about owning your catalog? What about licensing your songs for years to come?”
The future looks bright for Bennett, who’s particularly excited about performing upcoming tracks like “Champagne Tears” and continuing to push boundaries in hip-hop. His appreciation for platforms like TIDAL runs deep. “[Former TIDAL staffer] Jason Kpana was the first guy that I ever came and sat in an office with and played my music to … from that event to you guys doing events with Chance at Sox Arena and selling it out for thousands of people, there is no industry without TIDAL.”
“Dame Dash taught me something crucial,” Bennett reflects on his biggest lesson in the industry, recalling their conversation outside Chicago’s Soho House. “It’s like a light switch — when you do business, it’s emotionless. You have to be cold. Nothing should be personal. And if you’re an artist, you have to be vulnerable.” It’s this wisdom that has allowed him to successfully navigate both worlds, maintaining his artistic integrity while building Tay Bennett Entertainment into a formidable independent label.
As our conversation winds down, it’s clear that Taylor Bennett isn’t just finding his sound — he’s creating a new blueprint for artistic authenticity in the modern music industry. Whether he’s experimenting with pop-punk, returning to his rap roots or championing Chicago’s diverse musical heritage, Bennett remains committed to one principle above all: being unapologetically himself.
