Chappelle, one of the country's most sought-after yet reclusive comedians after walking away in 2005 from his still-influential Comedy Central show, spent three recent nights onstage at the Cellar, sometimes joined by friends, including Chris Rock, Kevin Hart, Marlon Wayans and Paul Mooney.
In jeans, a white long-sleeve T-shirt and black jacket, his hands frequently reaching for the cigarettes he's known to chain-smoke, Chappelle captivated the audience, many of them aspiring comedians. And during an exchange with Rock, he made news when he joked about the two of them doing a long-rumored tour together.
"You should come down to Palm Beach," Rock reportedly said to Chappelle.
"After next Tuesday," Chappelle said, "I'm free for like 11 years."
Chappelle has been known to pop up at comedy clubs for last-minute, unannounced shows, usually taking the stage well after midnight. But his latest three nights at the Comedy Cellar seemed the comedian's most serious flirtation with a more permanent return to the stand-up circuit.
Even Rock appeared to take the banter seriously. He discussed his tour availability onstage and, according to online reports, told Chappelle, "By Halloween I could do dates."
"This could be the show," Chappelle said to Rock after the two texted Jay-Z from the stage and left a voicemail for Arsenio Hall. "Fireside chats with Chris Rock."
"I'm in," Rock replied.
Chappelle has spent much of the last seven years with his family in rural Yellow Springs, Ohio, tucked in the sparsely populated plains that lie between Dayton and Columbus. The sleepy, largely white town allows Chappelle to lead a peaceful life where he can shop for groceries, eat at restaurants and drop by the corner store for American Spirit cigarettes with relatively little attention.
A longtime family friend of Chappelle's who attempted to reach out to the comedian for the L.A. Times on a recent trip to Yellow Springs came back empty-handed.
"You know how he is," the friend said apologetically. "Dave's just a reclusive dude."
Neither Rock's publicist nor the two publicists known to work with Chappelle returned requests for comment about a potential tour.
But the excitement generated online and among comedians at just the mention of a tour with or without Rock speaks to the lasting legacy of "Chappelle's Show," which was on the air for just 2 1/2 seasons starting in 2003.
The sketch comedy show, which featured over-the-top parodies and politically incorrect themes, quickly became one of the hottest shows on television and catapulted Chappelle into comedy's highest echelon and a $50-million renewal contract. He broke that deal when he took off for Africa without telling anyone he was leaving — and without finishing production on his third season.
The comedian insisted he just needed a break, but ultimately never returned to "Chappelle's Show."
"I can't think of anyone else in television history who made the kind of career move that he did — to walk away," said Tim Brooks, a television historian.
Individual "Chappelle's Show" sketches have amassed hundreds of thousands of views on Comedy Central's website, while the DVD boxed set of the show's three seasons has shattered sales records. The show's Season 1 sales in 2004 surpassed "The Simpsons" to become the overall bestselling television show on DVD at the time, according to Videoscan.
The past few years have seen a series of shows try to replicate pieces of Chappelle's formula for success — from Daniel Tosh's irreverence on "Tosh.0" to the focus on race and politics that permeates "Key and Peele."
But 10 years after its premiere, there has yet to be a comedy show that has found the commercial success and pop culture presence that "Chappelle's Show" held.
In the decade since its premiere, the show's intoxicating mixture of irreverent and defiant humor has been exalted as the most honest portrayal of hip-hop culture on television.
"His comedy is rooted in his understanding of history and his self-awareness of his own place in black and hip-hop culture," said Kevin Anthony Wisniewski, who edited "The Comedy of Dave Chappelle," essays about the comedian's significance. "There is a real intimacy in his work."
The show included Kanye West's first-ever televised appearance, as well as performances by Common, Big Boi and Mos Def.
"His take on hip-hop was genuine, which is why it was so well-received," said David Wall Rice, a Morehouse College psychology professor who has written about the show. Despite his close friendships with many of hip-hop's biggest names, Rice noted, Chappelle willingly parodied and ridiculed major hip-hop figures.
"The significance of Dave Chappelle is that he told the truth," Rice said.
Many consider "Chappelle's Show" to be a coming of age for the comedian whose previous on-camera highlight was the stoner cult classic "Half-Baked."
"'Chappelle's Show' defines the moment in history when he emerged as a voice of a generation," Wisniewski said.
The series included a now-notorious sketch about Clayton Bigsby, a blind black man who believed he was white and wrote white-power literature. Other popular sketches included one in which black America is paid reparations for slavery and another in which a racial draft is held and the races choose celebrities to represent them.
"The whole show reflected Dave's personal sense of humor, and it never felt like work when you were shooting with Dave," said Donnell Rawlings, one of the comedians who costarred in "Chappelle's Show." "It just feels like hanging out."
After Chappelle's sudden exit from the show, Rawlings and Charlie Murphy were tapped to host the third season, creating an awkward dynamic for the duo, both friends of Chappelle's. Neither had been given a head's up about his departure.
"I wanted to smack him and hug him at the same time," Rawlings said with a chuckle. "But it's Dave just, you know, being Dave."
Rawlings watched Chappelle's transition from on-the-edge comedian to reserved family man.
He recalled Chappelle telling him they were going out for pie to celebrate the birthday of the show's co-creator, Neal Brennan. Rawlings said he assumed "pie" was a comedic code word for getting high.
"When I get to the spot, I see Dave, Neal and an apple pie," Rawlings said. "Dave was at that place in his maturity where going out for pie actually meant going out for pie."
Just months later, Chappelle walked away from the show, his longtime writing partner Brennan and the limelight.
That act made Chappelle one of the nation's most sought-after interviews but other than a 2006 sit-down with Oprah, a 2011 appearance on San Francisco radio station and a full-length interview with James Lipton for "Inside the Actors Studio," the comedian is almost never quoted in the media.
By all accounts, he's actively attempted to regain the privacy he held before his international fame. But as he told Lipton, "Once you get famous, you can't get unfamous."
For Chappelle, stepping to the microphone at the Cellar marked a symbolic return to his roots.
As a teenager in the mid-'90s, Chappelle was a regular on the Cellar stage, delivering hundreds of stand-up sets.
"He has a gift. He can just get up there and talk about anything," said Noam Dworman, who owns the Comedy Cellar. "He doesn't even really need to hit punch lines very often. People will just sit there and listen to him."
Despite decades of friendship, Dworman said he can't predict if Chappelle will ever again step to the microphone as regularly as he once did. Others caution against reading too much into the comments about an impending comeback tour.
Chappelle, they insist, is just too unpredictable. Dworman, for instance, said Chappelle gives little warning when he shows up for an impromptu set at the Cellar. Sometimes he'll send word via a fellow comedian an hour or two before. Other times, he just walks in the door.
"That's just Dave being Dave," Dworman said.