“Had to go with what was the most sure shot”: Bryson Tiller reveals why he didn’t sign with Drake’s OVO

In a recent conversation with New Rory & Mal, Bryson Tiller opened up about his decision to sign with RCA Records instead of Drake’s OVO label early in his career. The 32-year-old singer from Louisville has spent 10 years in the music world since he dropped his first album, Trapsoul. He's kept in touch with big names like Drake, and they even made a song together in 2020 called "Outta Time."

Bryson Tiller said his choice to join RCA had to do with how things transpired. He didn't hear back from Drake at a key moment, which affected his decision.

“I’m being so blunt. Honest,” he began. “The only reason I didn’t sign [to OVO] is just because bro didn’t hit me back one time. This was in a moment when my label, like, they was hounding me, they was flying me, they was trying to get me away from Drake.”

“I was like, ‘Yo, OVO is really in my blood, for real.’ I really have studied [Drake’s] catalog. There’s a couple of people that I really consider huge strands of my musical DNA, and Drake is one of them,” he continued.

He texted Drake one last time, giving him another shot to get in touch before sealing the deal with RCA. When that effort didn’t yield a response, Tiller opted for the path that provided certainty.

“He never hit back,” Tiller added. “And I know he’s a super busy dude. I’m not saying that he didn’t want me to sign or whatever, but at that moment, like, I had a kid - people back home that’s looking at me like, ‘Is he gonna do it? Is he gonna make it?’ So I had to go with what was the most sure shot.”

“I hate being an artist. I only make music to feed my family .. if Drake or Chris Brown ask me to write for them forever, Iʼll quit making music.” – Bryson Tiller pic.twitter.com/JE7oGyeFjO

— Wealt (@teniolaSteph) August 22, 2025

Bryson Tiller on working behind the scenes and upcoming releases

Reflecting on his hypothetical career within OVO, Bryson Tiller said he would have been fine working in the background. He mentioned helping write for Drake and adding to projects without needing attention.

“When people would say, ‘Oh [Drake’s] gonna put you on the shelf, be in the sweatshop,’ I was like, ‘Cool. I’m cool with that.’ I was like, ‘Dog, I know how to write. I’ll write anything that he asks me to do and be just as rich,'” he said. “If you could take away all my fame right now, nobody recognize me, I’ll be so OK with it.”

On the creative front, Tiller continues to actively release music. His most recent project, The Vices, is part of a double-disc release, with the second half, Solace, scheduled for release on October 2.

Despite not joining OVO, Bryson Tiller has built a sustained career marked by creative output, collaborations, and a clear understanding of his artistic identity.