Weeks after hitting the stage during Drake‘s 2025 Wireless Festival headlining set, Bryson Tiller has opened up about his appreciation for the Toronto artist, his musical influence, and why he was never able to make things official with Drizzy’s October’s Very Own label.
During a recent sit-down on New Rory & MAL, the “Exchange” artist revealed that the only reason he didn’t sign to OVO was because Drake didn’t call him back in time before he felt pressured into signing with his label, RCA. According to the crooner, RCA was aware of his interest in signing to Drake’s label and continued to fly him around the country in an effort to keep them from crossing paths.
“OVO is really in my blood for real,” Tiller shared. “I really have studied his catalog. I mean, it’s a couple people that I really consider huge strands of my musical DNA, and Drake is one of them.”
Drake performs live on stage during day two of Wireless Festival 2025 at Finsbury Park on July 12, 2025 in London, England. Drake is headlining an unprecedented all three nights of Wireless Festival. (Photo by Simone Joyner/Getty Images for ABA)
He then recalls being flown from LA to Miami and then to New York, where he was asked to sign to RCA before being able to contact Drake about a potential deal. This inspired him to listen to Drake’s 2009 track “The Calm” and reach out one more time.
“I sent him one last text, just to see, like, ‘Yo, man. I don’t know what to do, blah, blah, blah,’ and he never hit me back. And I know he’s a busy, super busy dude, so not saying he didn’t want me to sign or whatever, but at that moment, I got a kid, and I got people back home looking at me like, ‘Is he gon’ do it? Is he gon’ make it?’ So I had to go with the most sure shot.”
Bryson Tiller performs onstage as a special guest of Drake during day one of Wireless Festival 2025 at Finsbury Park on July 11, 2025 in London, England. (Photo by Simone Joyner/Getty Images)
Co-host Rory then suggests Drake’s superstar-focus at the time would’ve likely taken his attention away from building up new talent. This is one reason he believes The Weeknd chose not to sign to OVO, adding that he possibly thought he, “could be just as big as you, so why would I sign to you?”
For Tiller, however, that wasn’t the case, confirming that superstardom has never been his goal. “I love making people happy with music and giving them moments and stuff, but as far as being on stage and being the most famous dude and everybody recognizing me, I just don’t care about that type of sh*t.”
Check out the clip here and the full convo below.