T-Pain surprised fans by playing Drake’s “Rich Baby Daddy” during his Lollapalooza set, despite previously calling out the Toronto rapper for not “gracefully” retiring from music.
The Chicago festival set was packed with tributes to legends like the Fugees and Michael Jackson, but when T-Pain dropped Drake’s track, he danced along without hesitation—making it clear that any lingering tension with the 6 God is a thing of the past.
Back in June, T-Pain revealed on the Crash Dummies podcast that Drake had once inspired him not to overstay his welcome in the music game—but pointed out that the Toronto superstar hasn’t exactly followed his own advice.
“One thing I learned from Drake, but one thing, he hasn’t followed his own words,” T-Pain said. “Drake said, ‘I wanna be one of them people that gracefully bow out and not get kicked out.'”
T-Pain then joked, “I have ever since said, ‘Thank y’all, I appreciate y’all. I’ll see y’all when I drop—don’t worry about it, I’ll just drop something. Let me know if you heard it.’ Drake is like, ‘No, listen. OK, I got another one. Hold on, check this out. Y’all ain’t like that one? OK, real quick, just one more. Let me try one more.’”
Drake caught wind of the comments and brushed them off as hate.
“This guy always had resentment for me [laughing emoji],” Drake wrote on Instagram. “You can hear it every time he speaks on my name.”
Offset also stepped in to defend Drake in an Instagram comment about the clip, writing, “Da Boy is da boy shit ain’t gone change. All dat hating on another grown man who do more numbers than everybody is Diabolical !!!!”
T-Pain’s remarks seemed to reference Drake and Lil Yachty’s 2023 chat, where Drake openly discussed his thoughts about eventually making a “graceful exit” from the industry.
“Well, I think like on a broader scale, I think I’m at the point now where I just wanna, like—I feel like maybe we talked about this the other day—but I feel like I’m kind of introducing the concept in my mind of a graceful exit,” Drake said at the time.
He also touched on why some rappers refuse to step aside.
“Sometimes it’ll baffle you, like why are these people still making attempts at trying to be present in the space?” he explained. “And then you’ll realize they probably, their needs and desires and their soul was probably fed for so long off of being a guy, or the guy, that they can’t let it go.
“So I guess what’s left for me is just to find a way to gracefully—I’m not ready now—but to gracefully continue making projects that are extremely, like, interesting and hopefully cherished by people,” Drake continued. “And then to find the right time to say like, ‘I can’t wait to see what the next generation does.'”
