The Trump on Roof Late-Night Jokes Were As Stale As Expected
Donald Trump has greatly benefited from the assumption that a man so stupid, so obvious, so foolish, couldn’t amass great amounts of power. It comes from the idea that the men who do wield great power are worthy of it by some sort of virtue or accomplishment, rather than ruthless exploitation and luck of birth. As we continue to learn just how many powerful men were willing to cavort with a prolific child rapist (for whatever reason), hopefully it will somewhat dispel the myth that these men are anything other than dick-led opportunists that lack integrity. It’s unlikely, though.
Instead, we will continue to suffer under the farce that Trump is some aberration of American power, not a symptom of it. While we live under that narrative, a small but not insignificant side effect will be that there won’t be any jokes about Trump that are funnier than his own antics. He is beyond parody.
Take Trump on the roof. On Tuesday, the president shocked the country by taking his retinue of guards and advisors on a walk around the roof of the White House. At one point, a reporter on the lawn called out to Trump: “Mr. President, what are you doing up there?”
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“Just taking a little walk,” Trump responded.
As images circulated of the president on the roof, there were plenty of people who started making jokes that he should join the White House dive team. It was perfect fodder; even better that his bizarre mid-morning sojourn coincided with the release of even more bombshell Epstein reporting, this time from the New York Times.
Of course, this incident made it to late-night television, where making fun of Trump has become central to the opening monologue. Case in point: Stephen Colbert opened the show with Trump on Roof.
“So often these days, folks, the news goes from stupid to sad to sadly stupid,” Colbert said. “But today, I’m happy to report it’s just plain dumb. Late this morning, the president held an impromptu press conference from a highly unusual location.”
He then cut to a clip of Trump kind of milling about, as another reporter shouts, “Sir! Why are you on the roof?” It’s worth noting that Colbert’s audience laughed the loudest at this, not any of Colbert’s following jokes.
“That’s nice. That’s not a question you hear asked of a world leader that often,” Colbert continued. “It’s right up there with your majesty, where are your pants?”
Colbert threw in a joke about Trump comparing the Capital Hill dome to a D-cup breast, before getting existential. “What does any of this mean? How are you the guy in charge? Why do we have to pretend? Why do we have to pretend it’s normal when an old man wanders around a roof and shouts at us?”
That’s where the bit ended. As far as jokes go, it was blah. Somehow, Jimmy Fallon took a slightly sharper aim when he also opened his show with Trump on the roof. “Uh, guys, this was strange,” Fallon began. “Earlier today, President Trump was spotted on the roof of the White House. This is real. Everyone was like, ‘Don’t do it, sir! Your approval rating isn’t that bad!’ And Trump said, ‘I’ll come down when you stop asking me about the Epstein files.’”
Fallon’s joke at least acknowledged what everyone else was thinking. The problem was that both bits felt obligatory, and that in both instances the in-studio audiences laughed harder at Trump saying “just taking a little walk” than any of either hosts’ jokes about it. That sheer audacity and expert delivery is something career comics spend decades perfecting.
Part of the problem is, these jokes really hinge on the premise that anything Trump does at this point is shocking, which is a reactionary failure of form for good jokes. It relies on the audience believing this is behavior unbecoming of, or out-of-character for, the man and the office of the President. That’s a hard premise to work from when the very same day Trump is doing a Distraction Walk on the roof, a story comes out revealing evidence that Epstein’s bedroom mantle was filled with photos of the pedophile arm-in-arm with U.S. presidents, prime ministers, members of the Royal family, tech billionaires and other heads of states. Even Noam Chomsky was there.
Beyond that, there’s also the issue that the hosts are having to deliver the jokes to a television audience that’s already beaten every bit of humor out of the situation in the 12 hours since it hit the internet. If you have 12 hours to come up with jokes, they have to be funnier and smarter than the 500 one-liners put on X/Twitter in that same timeframe.
That’s a very hard bar to clear, and it’s pretty clear our current slate of late-night hosts aren’t capable of clearing it.
