On the latest episode of The Daily Show, Jon Stewart took aim at Donald Trump‘s rambling speech during the White House Correspondents’ Dinner. The president spoke for nearly an hour during the annual event, which was rescheduled for Friday night after a gunman fired shots inside the Washington Hilton in April.
Stewart played a clip of Trump attempting to make a joke during the speech, which drew silence from the audience at the WHCD. “Normally I’d say, ‘Don’t quit your day job,’” Stewart said. “But in this case I will make an exception.”
Many of Trump’s cronies have praised the president for being funny, but Stewart wasn’t convinced. “When I was watching him do that one joke he doesn’t seem very funny at all,” Stewart noted. “Look, I’ve been in that situation. We all try new material. Doesn’t go well. On to the next one. You cannot judge Trump’s hour-long special just on that one joke.”
The host played another “joke” and broke down why it did not work, largely because Trump set up the premise and then rambled for four minutes. “You set up the premise and then you just walk out into the street?” Stewart questioned. He went on to break down several more jokes, none of which Trump was able to land.
“You don’t do jokes like you’re reading them for the first time,” Stewart exclaimed in frustration. “He’s putting 10 pounds of roast jokes into a five-pound bag. It doesn’t work this way! There are rules to these things.”
As he played more clips from the WHCD, Stewart offered Trump some advice about delivering jokes, including how to correctly roast someone and how to keep the audience engaged.
“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,” Stewart recounted. The host then offered a new segment he called “Shooting or Bombing,” which involved guessing which clips of the audience were from which event.
During his speech, Trump mocked CNN reporter for receiving an award and claimed he got her confused with Dylan Mulvaney. “I want to personally congratulate CNN’s Kaitlan Collins on receiving her award,” Trump said. “It was all about me. It’s a fake — she shouldn’t get the award, it was a fake. But I didn’t mind. I said, ‘Kaitlan, congratulations.’ But it was fake, there’s no question about it.”
The president went on to criticize Collins for never smiling. “You should be a happy person,” Trump said. “So smile, Kaitlan. Just smile.”
Stewart joked that Wolf Blitzer should have gone onstage to slap Trump, like Will Smith at the Oscars. “Look, this a bad night,” Stewart concluded. “Beyond the fact that Trump was terrible, the dinner should not have happened at all. In fact, it shouldn’t ever happen. Quite frankly, memorializing the collegial and cozy relationship between the press and those that they cover is, at best, a very bad look in normal times. I don’t need to see the cops and robbers getting along at a banquet honoring our penal code.”
Stewart called the event “an act of submission” because it involved the press participating with Trump. “You’d think you’d all be mad at him,” he said. “But they’re all in there just schnicking it up. So he just gets to shake hands with the leaders of a profession whose members he has subpoenaed, arrested, sued, cut their funding, threatened their licenses, barred their access, and even had fucking deported.”
Collins later joined Stewart to discuss her award and her reaction to Trump insulting her. “I was not surprised when he insulted me,” Collins told Stewart. “That happens pretty regularly inside the Oval Office. This is just a bigger venue where it was happening. What was most surprising to me was, the room was filled with a lot of his staffers, his cabinet, his allies, Republicans in Congress. It was so quiet in the room during the president’s remarks.”
Stewart praised Collins for being “unflappable” during her interactions with Trump, which clearly bothers him.
“I’ve always felt this, regardless of who’s the president, whether it’s Joe Biden, Donald Trump — those are the two I’ve covered — it’s really not about me,” Collins said. “And I don’t want it to be about my reaction. Instead, I think it’s more effective to remind people in those moments, when he is insulting me or when he is criticizing me, about the question I asked or the reporting that I did that he was so angry about in this moment. And the fact that I got an award for it really bothered him, clearly. And so I just think in those moments, it’s important to put the reminder back on the work, on the question, and on the non-answers that we get.”


