Jon Stewart Explains Why Trump’s Correspondents’ Dinner Set Bombed So Badly

"Honestly, the only funny part of the jokes was watching the crowd's reactions"

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Jon Stewart Explains Why Trump’s Correspondents’ Dinner Set Bombed So Badly
Author
Alex Young July 28, 2026

Donald Trump’s 65-minute set at the White House Correspondents’ Dinner was the kind of car crash many expected, veering between rants about his proposed White ballroom and Iran, and attempts at jokes targeting Bruce Springsteen and Alexandria Ocasio-Cortez.

On Monday night’s episode of The Daily Show, Jon Stewart did his best to determine where it all went wrong. While the material itself was obviously no good, Stewart pinpointed four main flaws with the dude delivering the lines: “The guy went four minutes before introducing the first joke in his own premise”; “You don’t tell us you’re changing the target of your roast joke halfway through the fucking joke”; “You don’t do jokes like you’re reading them for the first time”; and “Traditionally roasts work because at the heart of it all, you only roast the ones you love. Saying you hate someone in the middle of the joke really takes away a lot of the pleasure.”

Stewart continued: “Honestly, the only funny part of the jokes was watching the crowd’s reactions. It was a mélange of confusion, boredom, shock, and at one point, a literal existential crisis.”

“Here’s the one thing you never want from your audience at a comedy show: you never want the audience at your comedy show to clearly be rethinking the choices that led them to that night,” Stewarted added. “The audience was so distraught and perplexed that at times, it was difficult to discern whether you were watching their reactions to Trump bombing at this dinner or their reactions to a gunman interrupting the last one.”

From there, Stewart played a game with his audience in which he showed photos from the postponed White House Correspondents’ Dinner and the one held last weekend and asked them to guess which one was which. It was not as easy as you might have guessed.

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