Most shared humorous tales of personal experiences with Chappelle, and sincere stories that praised his big heart and big bent for making memories.
Legend talked about the unique musical jam sessions Chappelle hosts on a farm in his adopted home state of Ohio, and praised Chappelle’s 2005 Block Party documentary, in which he bussed residents of his town to Brooklyn for a concert featuring Legend, Kanye West, Common, the Fugees, Big Daddy Kane, the Roots and Adam Blackstone, who served as music director for the Twain event.
“Not only has Dave been one of the most gifted comics to walk the Earth, he’s a passionate champion of music, a curator of artists,” Legend said.
Uniting people, most of the time for what turns out to be an impromptu, one-of-a-kind experience, was a thread woven throughout the proceedings. It’s also likely the reason demand for tickets to last night’s ceremony was the greatest since 1998, when the inaugural Mark Twain statuette was awarded to Richard Pryor.
“He’s always bringing people together. He’s always been a leader in thought and culture,” Common told Billboard. “He says provocative things, and… it creates some uncomfortable conversations we don’t want to have but we need people like him because even if you don’t agree with them, it brings them up and then people have to discuss it. We need courageous minds like that.”
Common noted Chappelle’s jam sessions feature not only musicians, but politicians, athletes and others. “There aren’t many people who can get LeBron [James] to come and Jay-Z and Beyonce, and get Kendrick Lamar,” Common said, noting that during an eclectic gathering at the White House during the Obama Administration, the President referenced Chappelle’s unique ability to connect people. “He said, ‘Look Dave Chappelle, I’ve got my own Block Party now.’ “
The connection between the arts is not lost on Chappelle, who first began honing his comedy while attending the Duke Ellington School for the Arts; in 2017, he staged a two-week concert series at Radio City Music Hall where musicians and comics shared the stage.
“An honor like this would be special anywhere it happened, but the fact that it’s happening here in Washington does make me feel like I’ve closed some sort of circle,” he said. “And I came home and everyone’s OK. My friends still love me and everything still feels right.”
Ellington’s Radical Elite Show Band performed a spirited version of Chappelle favorite, Prince’s “Let’s Go Crazy,” to open the annual gala, which raises money for programs at the national arts center.
“I came up in the era of hip-hop, and some of the best practitioners of hip-hop are people my age. They took this genre that was obscure and took it to the mainstream, and while that was happening, we were all friends,” Chappelle told Billboard. “These people are a huge part of my life. I couldn’t imagine doing a night like this without my comedian friends or my musician friends. It seems wildly appropriate we all do this together.”
Other segments of the event focused on the 46-year-old’s comedy specials and TV work, notably Chappelle’s Show, his long-running series on Comedy Central that Chappelle walked away from in 2006.
Chappelle returned to the airwaves in 2017 with his first set of Netflix specials. His latest, Sticks and Stones, earned him his first appearance on a Billboard chart. The comedy album debuted at No. 4 on Top Comedy Albums in early October.
Noting Comedy Central had offered Chappelle $50 million to stay, fellow network alum Stewart said, “The courage it takes as a performer and artist to stand up for who you know you are… is just one more reason we all love and respect and admire this man.”
For his part Chappelle—lighted cigarette in hand—used his closing remarks to make a statement about freedom of speech.
Noting he’d fight for the right of all comics to speak their minds, he said, “This is the truth and you are obstructing it. I’m not talking about the content. I’m talking about the art form. Do you understand?” he said. “The First Amendment is first for a reason. The Second Amendment is just in case the first one doesn’t work out.
“I love my art form,” he added. “It saved my life."