Dave Chappelle Brings Electric Energy to Co-Headlining Show with Jon Stewart at Apollo Theater

For a one-night-only double bill at Harlem’s famed Apollo Theater, two of the biggest comics in the world, Jon Stewart and Dave Chappelle, joined forces to skewer President Joe Biden, Donald Trump, Israel and members of the audience in a night of comedy that felt electric because it came at such a strange moment for the country.

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The night of top-tier comedy started bumpy for the Apollo Theater. The famed hall in the middle of 125th Street has been a center of creativity and Black culture in Harlem and New York for nearly a century. But on Saturday, management and staff had the unenviable task of ensuring that no one had access to their cell phones during the show.

Stewart, who has a freshly raised profile now that he is back hosting The Daily Show (on Mondays only), was in great form as he dropped his unfiltered and very funny takes on Biden’s debate performance and candidacy and Trump’s, well…Trumpiness. And while running short on time, he also quipped about his son, who spent some time as a toddler naked in a cowboy hat with jelly strategically smeared on his body.

Stewart’s set, the first of the two, was of the moment, given Biden stepped down from the 2024 election the very next day. Stewart’s talent for self-depreciation while tearing down the powers that be is unmatched, and was on full display at the Apollo stage on Saturday night.

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There’s something about that moment when Dave Chappelle grabs a mic, stands (or sits) onstage before a live audience and just riffs. Some of the best gags of the night came early in his set, when he explained that fame is like running up a hill with bullets constantly whizzing past your ear, a reference to Trump’s recounting of the assassination attempt last weekend, and also joked about Sean Combs — “Oh, shit! They got Puff Daddy — in a reference to the rapper’s legal issues which include accusations of assault and sex trafficking.

Some of the topics Chappelle tackled include Trump, Biden, fame, Ohio’s men and Gaza . On politics, he pointed out how the entire process is an ouroboros, or a snake eating its own tail. He also quipped that 2024 is the first year that white voters get to feel as hopeless about no-good candidates as Blacks do every year. His set grew unpredictable at times, with Chappelle shouting back at hecklers who had beef with the comic.

The night closed with Stewart joining Chappelle on stage for a performance that brought some of the best gags they had. The two comics are old pals and it shows. It was also revealed that Chappelle relentlessly pursued Stewart as a 2020 presidential contender. Given the tenor our nation’s politics, he may still be nagging his friend to jump in.

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