People Askin’ Questions: Will Dave Chappelle Make an Ali-Comeback and Reclaim His Crown From Kevin Hart?

There’s a scene in Kevin Hart’s BET mockumentary Real Husbands of Hollywood when he’s engaged in a volley of putdowns with Nelly. Paraphrasing the scene, Hart is greasing Nelly for his lack of recent hits and Nelly, looking for a way to diminish the comedian, dismisses Hart’s recent success as the product of a void. He basically tells Hart that he’d still be a C-list comedian making straight-to-DVD movies if Dave Chappelle weren’t off somewhere in Africa. Watching this scripted exchange, you were still left with feeling that everyone — most of all Hart — found a kernel of truth in Nelly’s observation.

Chappelle famously left the spotlight eight years ago. The stand-up mantel that he assumed from Chris Rock went unclaimed for a while. Rock’s frequent collaborator Louis CK sort of took over the role of most acclaimed and popular comedian, but it wasn’t until the last couple of years when K-Hart was putting his stand-up films in theaters to eight-figure grosses that you witnessed the Rock/Chappelle void dissipating. This was especially the case for the lineage of black comedians that has had a clear timeline of champions (Bill Cosby to Richard Pryor to Eddie Murphy…). It’s similar, perhaps, to the King of Rap mantel that went virtually unclaimed in the years after Biggie and Tupac’s deaths, as Snoop’s career dipped while he played around with No Limit, Nas continued what would be a career-long dance of unease with the mainstream and Jay-Z was more burgeoning bluster than an actual, assured icon.

With the backdrop of Hart’s smash hit Let Me Explain — the fourth highest grossing stand-up concert film of all-time, clocking in at just over $32 million — we are amid Chappelle’s “return to the spotlight.” He’s headlining the Oddball Comedy and Curiosity Festival, which kicks off a 15-city tour this Friday in Austin, Tex. You gotta wonder if Chappelle will reemerge as anything close to the juggernaut he was when he left the game at his apex.

Very few of us have been privy to Chappelle’s sporadic dates and drop-ins over the past couple of years. (I want to jackhammer a hole through my head every time I catch word that I missed one of his impromptus at the Comedy Cellar in the West Village.) Jason Zinoman, who wrote the recently released “Searching for Dave Chappelle,” has seen Chappelle at enough recent stops to offer a narrative on the evolution of his new routine. He wrote about it in a recent New York Times piece giving this insight:

Mr. Chappelle may be fixated on the past, but the style of his comedy is increasingly distinct from a typical comedy club set, forging his own way forward. Mr. Chappelle has always preferred ambling yarns to quick jokes, but his new material stretches the limits of stories, telling long, herky-jerky tales propelled by quick pivots in tone and perspective. An extremely patient comedian, Mr. Chappelle is now making a commitment to establishing scenes, mapping out descriptions of characters that are almost literary in their detail.

An epic 10-minute story about a charged exchange with a homeless man he meets outside his upscale Manhattan hotel had the poetic weight of an August Wilson monologue. Since San Francisco, this morally engaged story has become more ornate and moody, the jokes emerging from meticulously sketched vignettes.

In the recent documentary Richard Pryor: Omit the Logic, Marina Zenovich reveals that Pryor bombed in his first show back from very public hiatus, a show that was his comeback event after burning himself while freebasing. This bombing may be common knowledge to some, but it was news to me. After throwing up a dud in front of a star-studded crowd and anxious fans and cutting his first comeback show short, he came back the next night and killed for what is now his iconic Live on the Sunset Strip. No one swooped in to take Pryor’s crown while he was away dealing with his demons (in Africa, much like Chappelle), but that doesn’t take away from the way he came back from what could have been a career-ender and spit out a Mona Lisa. Within a few years Eddie Murphy was grabbing the baton.

Were Louis and K-Hart just placeholders? Or is Chappelle — who left the stage as a conscientious objector — making an Ali comeback? People askin’ questions.

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