Dave Chappelle surprised fans with an unexpected appearance during Maxwell’s performance at the Roots Picnic.
The comedian addressed the audience during the R&B legend’s headline set on Saturday (May 31) and commended The Roots for putting together the event while celebrating Maxwell’s career achievements.
“This is outstanding. Make some noise Philadelphia, the city of Brotherly Love,” said Chappelle, as seen in a video making the rounds online. “From the front to the back, all I see is beautiful black people. I don’t see no violence, I don’t see no hatred. I just see love and community. I flew all the way from Ohio to fuck with that.”
“When I met Maxwell, I was on a date with the woman that’s now my wife. He was a bartender at a restaurant in Union Square, you remember?” Chappelle recalled, referencing his now-wife Elaine Chappelle whom he married in 2001. “If I said this to this n***a, ‘orange juice and cranberry,’ he’ll choke me to death,” he joked, as the crowd laughed.
Following the comedian’s exit, Maxwell returned to the microphone and shared his own memories of their early encounter.
“I don’t think Dave remembers but when I saw him, I walked up to him and I said, ‘You know, you’re really funny, bro. You should really keep doing this.’ And this is really true,” Maxwell said. “I walked up to him and told him that I was a waiter. God is good is all I’m trying to tell y’all.”
Maxwell joined the 2025 Roots Picnic roster as a replacement after D’Angelo withdrew due to ongoing surgical recovery.
The yearly music festival, created by The Roots, runs through today (June 1) at Philadelphia’s Mann Center for the Performing Arts and showcases performers like Lenny Kravitz, Meek Mill, GloRilla, Miguel, Tems, Latto, Pusha T, 2 Chainz, Jeezy, Jagged Edge, and others.
