After White House Correspondents' Dinner, Jon Stewart attempts to teach Trump how jokes work

The Daily Show host also brought CNN reporter Kaitlan Collins to the show for some level-headed questions about the press.

By Drew Gillis  |  July 28, 2026 | 9:52am
Image courtesy of Comedy Central
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After White House Correspondents' Dinner, Jon Stewart attempts to teach Trump how jokes work

As we know, this weekend’s White House Correspondents’ Dinner was a bust and a bomb, and we’re really only talking about the jokes delivered by President Trump at the event. You have to specify, because the last time there was one of these events, it ended early because of gun fire. This allowed Jon Stewart to play a little game he dubbed “Shooting or Bombing,” comparing clips from the respective dinners and asking his audience which was which. The crowd in the room looked generally more miserable the second time when they just had to listen to Trump talk. 

After hearing in the lead-up to the event how funny the president is, expectations for his act were high. Though he couldn’t deliver, Stewart tried last night on The Daily Show to give him some comedy lessons. Namely, he suggested he stick with some simple set up-punchline quips, instead of a meandering four-minute rant about the politicians he hates. This proved to be nearly impossible, as those who already saw the dinner know. But it’s clearly still fun for Stewart to bring attention to something Trump is obviously very bad at… until it isn’t. Near the end of his segment, Stewart brings up the award presented to the Wall Street Journal for its reporting on Trump’s relationship with Jeffrey Epstein, which resulted in a lawsuit from the president. This moment, says Stewart, “solidified that this event is worse than pro-forma. It’s actually an act of submission.” 

Later in the episode, Stewart brought out CNN journalist and frequent Trump target Kaitlan Collins for a very measured conversation about her coverage of the White House, which is worth watching.

 
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