Music

Drake Is All Smiles While Being Told to 'Keep Holding Your Head Up' by Charleston White

"You the best," White told Drake during a stream with Adin Ross.

Drake in a black leather jacket at a crowded event, with people in the background.
Image via Getty/Cole Burston

Charleston White wants Drake to know he considers him “the best.”

During a recent streaming appearance alongside Adin Ross and others, the comedian and internet personality shared some words of encouragement for the OVO Sound co-founder over FaceTime. Drake, as seen below, couldn’t help but laugh through most of White’s remarks, which notably come after “What Did I Miss?” signaled the presumably imminent arrival of a new solo album.

“You keep holding your head up, n***a,” White told Drake, who will later his week headline all three nights of Wireless Festival in London. “You the best. Don’t let ‘em tell you nothing else. You the best, n***a.”

White went on to jokingly mention both Bernie Mac (RIP) and Michael Jordan.

“If you were Black as Bernie Mac, they’d hug on you, but you a yellow n***a doing it like that,” White joked. “If Michael Jordan was a yellow n***a jumping from the free throw line, they wouldn’t wear his tennis shoes.”

Elsewhere, Drake asked Ross to send him “the flight manifest” for a planned plane full of streamers bound for Wireless.

“I’m gonna get the jet,” Drake, repeatedly (and fittingly) referred to as “Iceman” during the stream, said.

Drake’s upcoming album, seemingly titled Iceman, marks his first solo full-length since 2023’s For All the Dogs. Back in March, Drake teased that his “next chapter” might leave some “feeling uneasy.”

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