The Daily Show’s Jon Stewart reacted on Comedy Central on Monday to President Trump’s Friday’s White House Correspondents’ Dinner address by criticizing the media for inviting “your opponent” to an event supposedly meant to celebrate the First Amendment. Later, he welcomed CNN’s Kaitlan Collins to the show and lamented that “this cannot be real” and “that guy runs us.”
At one point during his monologue, the 1997 WHCD comedian suggested it was time to shut the dinner down for good, “Look, beyond the fact that Trump was terrible, the dinner should not have happened at all. In fact, shouldn't ever happen. Memorializing the collegial and cozy relationship between the press and those 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.”
Jon Stewart criticizes the White House Correspondents Dinner for inviting Trump "You can celebrate the First Amendment without asking your opponent in that fight what he thinks. You already know what he thinks." (1/2) pic.twitter.com/OAoXtBkVlA
— Alex Christy (@alexchristy17) July 28, 2026
However, for Stewart, inviting Trump was a whole order of magnitude worse, “You can celebrate the First Amendment without asking your opponent in that fight what he thinks. You already know what he thinks.”
Stewart then played a montage of clips of Trump attacking the press by calling them “fake news” and other familiar Trump lines, but nothing to suggest that the First Amendment was actually in any danger.
Nevertheless, Stewart later asked Collins, “There are times when I watch him and I think to myself, this cannot be real. Like, this can't be America. America. You have heard of us. We’re great. Yes. We are—we’re number one. We’re the best. That guy runs us? What? In the room that night, did it feel surreal? Did he—was he bombing as hard as it appeared on the TV?”
Collins began by replying, “You know, I have covered Trump for ten years, so I have listened to pretty much all of his speeches for ten years, with very little exception, and so I actually think it is helpful for other people to be able to listen to them in their entirety, which people really don't that much these days. In the room, I think I was not surprised when he insulted me. That happens pretty regularly inside the Oval Office. This is just a bigger venue where it was happening.”
She then gave Stewart the answer he wanted, “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.”
Most conservatives would not complain if Stewart got his wish and the WHCD ceased to be a made-for-TV spectacle where journalists tell other journalists how awesome they are, but what Collins and so many of her colleagues fail to appreciate is that Trump’s routine turned the tables on the dinner after years of gratuitously nasty jokes about conservatives. Trump may have said Collins looks like Dylan Mulvaney, but Wanda Sykes wished that Rush Limbaugh would die.
Here is a transcript for the July 27 show:
Comedy Central The Daily Show
7/27/2026
11:19 PM ET
JON STEWART: Look, beyond the fact that Trump was terrible, the dinner should not have happened at all. In fact, shouldn't ever happen. Memorializing the collegial and cozy relationship between the press and those 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. You can celebrate the First Amendment without asking your opponent in that fight what he thinks. You already know what he thinks.
…
11:28 PM ET
STEWART: There are times when I watch him and I think to myself, this cannot be real. Like, this can't be America. America. You have heard of us. We’re great.
KAITLAN COLLINS: Been here. 34 years.
STEWART: Yes. We are—we’re number one. We’re the best. That guy runs us? What? In the room that night, did it feel surreal? Did he—was he bombing as hard as it appeared on the TV?
COLLINS: You know, I have covered Trump for ten years, so I have listened to pretty much all of his speeches for ten years, with very little exception, and so I actually think it is helpful for other people to be able to listen to them in their entirety, which people really don't that much these days.
In the room, I think I was not surprised when he insulted me. That happens pretty regularly inside the Oval Office.
STEWART: Yes.
COLLINS: 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.
