Dave Chappelle reveals Maxwell’s profession before becoming an R&B icon during his surprise appearance at Roots Picnic

V103 Winterfest - Source: Getty
Maxwell performing live during the 2022 V103 Winterfest at State Farm Arena in Atlanta, Georgia. (Image via Getty/Paras Griffin)

Dave Chappelle is recalling Maxwell's good-old days of waitering before he became the legendary R&B icon he is today.

During a surprise appearance on Maxwell's headlining set at the Roots Picnic this Saturday, May 31, the actor and comedian addressed the crowd as he lauded The Roots for pulling off the event. He then turned to his friend and congratulated him for how far he has come in his career.

"This is outstanding. Make some noise Philadelphia, the city of Brotherly Love," Chappelle said, as seen in clips going viral 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 f*ck with that."

He went on, as he referenced his wife, Elaine Chappelle, whom he married in 2001, per Complex:

"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?” He added, “If I said this to this n***a, ‘orange juice and cranberry,’ he’ll choke me to death."

Shortly after Chappelle left the stage, Maxwell took back control of the mic as he reflected on his early days himself:

"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,” he 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."

Everything we know about this year's Roots Picnic as Maxwell steps in for an ailing D’Angelo

At this week's Roots Picnic, which was held at the Mann Center in Fairmount Park in West Philadelphia, Maxwell delivered a performance for fans gathered outside. The singer replaced D’Angelo as the headliner as the latter backed out, citing a medical concern:

"Due to an unforeseen medical delay regarding surgery I had earlier this year, I’ve been advised by my team of specialists that the performance this weekend could further complicate matters," D’Angelo said in a post on Instagram.

Several lanes and roads were closed or restricted for the annual event, which was launched in 2008. Streets closed till today, June 2, include North Georges Hill Drive, between Belmont Avenue to 52nd Street; Wynnefield Avenue, between Parkside Avenue and Belmont Avenue; and South Georges Hill Drive, between North Georges Hill Drive and Belmont Avenue.

The streets that are expected to be closed until 6 p.m. Wednesday, June 4, includes South Concourse Drive, between Belmont Avenue and 52nd Street, and Avenue of the Republic, between Belmont Avenue and 52nd Street.

The two-day festival, formed by the renowned hip-hop group, The Roots, will also play host to performances from Lenny Kravitz and Meek Mill, GloRilla, Miguel, Tems, Latto, Pusha T, 2 Chainz, Kaytranada, Jeezy, Musiq Soulchild, Kur, Elmiene, Jagged Edge, and Cee Lo Green.

Single-day tickets are still on sale and retail for $125. As per NBC Philadelphia, the two-day passes currently retail for $225.


As for Grammy Award-winning crooner Maxwell, he last performed in Philadelphia back in September last year, as part of his Serenade Tour.

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Edited by Amey Mirashi