The connection between the honoree and namesake of Dave Chappelle: The Mark Twain Prize, which airs Tuesday at 9 p.m. ET on PBS (check local listings), is made almost immediately by comic Sarah Silverman: "You both love using the n-word!"
Honoring Chappelle, a Washington, D.C. hometown hero who is the 22nd recipient of The Mark Twain Prize for American Humor, means an appearance by the marching band of his alma mater, the Duke Ellington School of the Arts, playing Prince's "Let's Go Crazy" to start the long event, taped in October at the Kennedy Center, which will likely the most-bleeped program in public television history.
An array of musicians and hip-hop artists — including Common, John Legend, Q-Tip, Erykah Badu and Yasiin Bey (formerly Mos Def) — join the comics on the roster, which include Tiffany Haddish, Jon Stewart and Aziz Ansari.
That's done in part to reflect the way Chappelle has always brought together artists and musicians, in the manner of his 2005 film Dave Chappelle's Block Party that served as a coming-out party after he abruptly quit his wildly successful Chappelle's Show that made him a superstar.
Morgan Freeman serves as a master of ceremonies for an event that drew another Hollywood star to the stage in Bradley Cooper, who directed and co-starred with the comic in A Star is Born, calling their scene together "probably the best scene I've ever done with another actor."
But the Kennedy Center audience is filled with celebrity friends, including Chris Tucker, Chance the Rapper, Michelle Wolf, Jeff Ross, Marlon Wayans, and George Lopez — as well as the patrons of the Kennedy Center.
"I had no idea you had so many old white fans," says Michael Che of Saturday Night Live. "I feel like I died and went to Brooks Brothers."
He hails Chappelle as someone "willing to make fun of you whether you're white or gay - end of list," a reference of criticism to Chappelle's latest Netflix special Sticks & Stones that premiered in August.
Che was among a group of presenters who agreed to participate so late, they weren't in the printed program, including Ansari, Badu and SNL compatriots Kenan Thompson and Colin Jost, who call the 2016 post-election hosting that won Chappelle an Emmy "as the best episode that we've been there for."
SNL creator and past Twain winner Lorne Michaels says he fought to get Chappelle to be the perfect host days after the 2016 election whatever the outcome, and though he didn't know what the comic was going to say in his monologue until he did it, he did not disappoint. "It was a landmark show," he says. "It was perfect."
Haddish, who came dressed in the kind of green jumpsuit Chappelle sported in the latest special, calls him a mentor and big brother but chided his singing of Prince songs.
Silverman praised Chappelle's ability to observe and take in details others would miss, such as when he returned from Hollywood early to say he finally visited Compton and was struck that everybody had lawns.
Chappelle spent part of his growing up in Ohio, where he now makes his home in what Buckeye native Legend calls "the kind of town that makes people say, 'Why does Dave Chappelle live here?'"
But the comic has thrived and connected there, most recently organizing a concert in Dayton to promote healing shortly after the August mass shooting.
Neal Brennan, a longtime writing partner who co-created Chappelle's Show, says the comic initially tried to pitch a show based on the old Playboy After Dark, "which, if you can remember that, get your affairs in order, because you're on death's door."
That show never came to pass, but the 2003 Chappelle's Show, which found the star improvising some of the most famous bits on the spot, did go "absurdly well," Brennan says, "like, so-well-you've-gotta-go-to-Africa well."
Walking away from the Comedy Central hit, after being offered $50 million for a third season, and flying off to South Africa, got the attention of his fellow Comedy Central star Jon Stewart of The Daily Show — not for holding true to his values despite the promised windfall, but that the cable network had $50 million to offer in the first place.
"I knew that money was going to need a home," jokes Stewart, who became late night's highest-paid host until he left in 2015. "Dave, I want you to know I raised that money like it was my own."
Chappelle basks in the tributes from a box seat alongside the stage with his wife, children, and his mother. "You have no idea what I've put this woman through," he says in brief remarks at the end, in which he mostly praises the freedom comics have to comment on the world, even if you can't agree with all of it.
"It's an incredibly American genre," Chappelle says. "The First Amendment is first for a reason. The second one is in case the first doesn't work out."
Chappelle followed past Mark Twain Prize recipients Richard Pryor — the first in 1998 — George Carlin, Bill Murray, Tina Fey, David Letterman, and two Chappelle helped induct - Lily Tomlin in 2003 and Eddie Murphy in 2015.
"To be on a list with Richard Pryor is actually unfathomable. Nobody would actually feel worthy of it," Chappelle said on the red carpet before the taping. Some of the past recipients from Carlin to Murphy "really shaped my imagination, my life. I'm a comedian, so these are the shoulders that I stand on that are on the list. And you know I hope one day someone would look at me the same way and literally stand — I could build something that people could stand on."
Murphy didn't attend the Twain Prize event — though the two were reunited during the Murphy-hosted SNLin December. But in a taped message, Murphy called Chappelle "the voice of his generation, no question. Nobody is more deserving of this honor."