Jon Stewart Tears into Trump’s Chaotic WHCD Roast with Mock Comedy Lesson

Jon Stewart turned President Donald Trump’s White House Correspondents’ Dinner speech into an impromptu comedy masterclass on Monday night, mocking the president’s meandering attempt at a joke and offering a few lessons on how to actually land a punchline.

“Friday night was the White House Correspondents’ Dinner. As you can remember the first attempt ended prematurely. The frightening scene prevented the president from delivering his humorous remarks – prepared remarks – which was a shame,” Stewart said as he opened The Daily Show.

“Because if there’s one thing that President Trump is known for, it’s his joyful love of mirth,” he deadpanned.

After airing a montage of cable hosts praising Trump’s sense of humor, Stewart wasn’t convinced: “Funny how? Does he amuse you? What’s so f*cking funny?”

Still, Stewart insisted one bad routine wasn’t enough to judge a comic: “You know what? We all try new material — it doesn’t go well. You move on to the next one. You cannot judge Trump’s whole hour-long special just based on that one joke. Mr President, what else you got?”

He then rolled footage from Trump’s dinner speech, in which the president proposed staging UFC fights on the White House grounds every Friday.

Stewart initially approved: “See, this is great. Simple premise, easy and refillable. ‘We’re going to be hosting more fights.’ So, these are just going to be jokes about who’s on the card, what the fights are going to be. It’s simple – setup, punchline.”

“Or…” he added, before letting the clip continue rolling.

Instead of delivering the joke, however, Trump spent nearly four minutes — noted by an on-screen Daily Show timer — veering into tangents about the Indy 500 and Fourth of July celebrations before returning to the original premise.

“You set up the premise then you just walk off into the street?!” Stewart exclaimed, pausing video for his critique. “The guy went four minutes before introducing the first joke fight in his own premise!”

When Trump finally reached the punchline, he first named former New Jersey Governor Chris Christie as “the heaviest of the heavyweights” before abruptly changing course and deciding it would instead be Rep. Jerry Nadler (D-NY).

“What? Oh my God!” Stewart interrupted. “You don’t tell us you’re changing the target of your roast joke halfway through the f*cking joke. We don’t know the target — just change it, don’t say ‘I was going to make fun of the governor of Illinois but Jerry Nadler.’”

He piled on by mocking the joke’s targets:“Oh, wait till the former governor of New Jersey and outgoing congressional district 12 representative of New York get a load of this! Their careers will continue to have been over.”

After Trump added another punchline about the pair fighting over a “fat piece of cheesecake,” Stewart could only stare into the camera in disbelief.

He then decided to coach the president through another joke, this time about Rep. Alexandria Ocasio-Cortez (D-NY): “Look, this is a solid premise. Let’s try this again. Here’s an easy joke to land with this premise. ‘Oh, and tonight, I’m proud to announce the next upcoming fight at the White House, AOC will face off against her greatest enemy – a simple question about foreign policy.’”

“See, it’s simple. Give that joke a go,” Stewart said, before returning to roll tape of Trump.

“And then you have a Congresswoman Alexandria Ocasio-Cortez – AOC plus three – that’s her three friends, right?” Trump began, as Stewart’s confidence immediately and visibly evaporated. “AOC plus three. And I watched her give that answer when she was over in Europe. It was not a good answer. If I ever gave that answer, I would be out of politics –”

“You don’t have to talk about what you –” Stewart tried to interject, as Trump continued: “You cannot have a 19 second wait time to –”

“Just f*cking do the joke!” Stewart shouted at the video.

Trump eventually arrived at the punchline: “But we’ll then have a rematch against an extreme simple question on a foreign policy.”

“Nobody knows what you’re saying now!” Stewart cried. “You don’t do jokes like you’re reading them for the first time! God!”

Watch above via Comedy Central.

New: The Mediaite One-Sheet "Newsletter of Newsletters"
Your daily summary and analysis of what the many, many media newsletters are saying and reporting. Subscribe now!