Jon Stewart Says Donald Trump Should 'Quit His Day Job' and Try Comedy After 'Bombing WHCD Speech'

Jon Stewart thinks President Donald Trump should rethink the comedy career.

On the July 29 episode of “The Weekly Show” podcast, Stewart revisited Trump’s White House Correspondents’ Dinner speech and offered the kind of advice one comic extends to another.

“As a comedian, you know, when you watch somebody bombing like that, the traditional thing to say is, ‘Hey, don’t quit your day job,’” Stewart said. “But I think in the president’s case, I think we would all make an exception.”

But he also suggested Trump might still have room to grow.

“I think he can improve,” Stewart joked. “I think he’s got some timing. But the weave didn’t quite work with some of the more concise roasts.”

Stewart also used the podcast to revisit Trump’s latest attacks on CNN chief White House correspondent Kaitlan Collins, who had appeared with him two days earlier on The Daily Show.

Collins received the Award for Excellence in Presidential News Coverage Under Deadline Pressure at the July 24 WHCD for her coverage of Ukrainian President Volodymyr Zelensky’s 2025 Oval Office visit. Trump used part of his speech to call the award “fake” and complain that Collins does not smile. He also compared her to actress and transgender activist Dylan Mulvaney while referencing Mulvaney’s 2023 Bud Light controversy.

“Once again, in the battle between Kaitlan Collins and Donald Trump: point, Collins,” Stewart said.

He estimated the score between them at “somewhere around 328 to zero,” adding that Collins’ “sophistication, focus, and class” is “just wiping the floor with that dude.”

When Collins appeared on The Daily Show, she told Stewart she was not surprised by Trump’s WHCD remarks.

“In the room, I think... I was not surprised when he insulted me,” Collins said. “That happens pretty regularly inside the Oval Office. This is just a bigger venue where it was happening.”

Stewart framed the dinner as difficult terrain for Trump’s usual insult-comedy style.

“We’re all recovering from the bombing raid that the president of the United States pulled on the White House Correspondents’ Dinner,” Stewart joked. “Not so f---ing easy, is it, buddy boy!”

His latest comments came during a podcast episode otherwise centered on AI. Stewart’s guest was Cory Doctorow, author of The Reverse Centaur's Guide to Life After AI, for a conversation about AI hype, surveillance, labor exploitation and corporate consolidation.