Donald Trump spoke for nearly an hour at the United Nations General Assembly session in New York, almost three times the allotted slot. The speech came the same day Jimmy Kimmel returned to TV screens after being reinstated by ABC. The two juxtaposed a curious intersection of the American zeitegeist which can be broken down into three distinct parts: the comedic, the tragic, and the politics.

The Comedic

During Trump’s speech, in his classic weaving style which is eerily similar to the literary stream-of-consciousness James Joyce approach, the leader of the free world complained about escalators, teleprompters, India, China, Barack Obama playing golf and lamented the fact that he didn’t get the contract to redo the United Nations building before delving deep into its aesthetical problems. He bragged about fixing the economy, stopping migrants, ending “seven wars,” sending illegal aliens to different countries and making NATO bend to his will. He complimented his wife’s physique, warned that London would fall to Sharia Law, and blamed immigration and green energy for all the world’s problems, claiming that strong borders and traditional energy sources were the key to happiness. And in that duration, he was funnier than Jimmy Kimmel ever has been.Trump didn’t even have a functioning teleprompter. And yet he was funnier, than Jimmy Fallon, Stephen Colbert, John Oliver, and any other “comedian” that clings to a desk at 11PM and pretends to be America’s “conscience.” He was born with better comic timing than their monologues ever had. Every rally he holds is essentially a comedy special, complete with callbacks, audience interaction, and improv. No writers’ room, no punch-up meetings—just a septuagenarian free-styling nonsense that makes his crowd laugh harder than any Kimmel bit.Once upon a time, late-night comedy mattered.

Jay Leno roasted Bill Clinton, David Letterman mocked George W. Bush, and Jon Stewart castigated the Iraq War. People stayed up to watch because they felt like these hosts were taking risks. But now? Monologues sound like they’re written by a DNC intern with a TikTok addiction. The jokes aren’t jokes anymore; they’re moral lessons with a punchline stapled at the end. Kimmel is less a comedian and more a priest, blessing his audience with the approved take of the day.Comedy, as a cultural force, migrated.The young aren’t watching late-night—they’re watching Joe Rogan smoke cigars with neuroscientists, or Andrew Schulz riff about cancel culture, or YouTubers who don’t care about advertiser-friendly guidelines. Newsbusters calculated that late-night hosts invited conservatives just 14 times compared to 511 liberals—this in a country where Trump won the popular vote in 2024. The disconnect is glaring.When Jimmy Kimmel returned to ABC, he delivered what the New York Times called a “somber but defiant” monologue about free speech. He wept, he thanked Ted Cruz and Mitch McConnell for defending his right to speak, and he even brought out Robert De Niro in a mob skit about the FCC. It was meant to be defiance, but it played like penance—an overwrought sermon to an audience that has already moved on. Compare that with Trump at the UNGA the very same week, rambling about escalators and Sharia law.One sounded like a late-night host trying to be a statesman; the other sounded like a statesman doing late-night better than the hosts.One could argue that humour is subjective and beyond political affiliations, but late-night hosts have become so obsessed with being voices of morality that they forgot to add the humour. The stage lights are on, the laugh track still plays, but the audience left years ago. The only real comedy happening in American politics today is Donald Trump, and he’s funnier than all of them because he’s not trying to be. He’s the jester and the king rolled into one, and that makes the rest of them irrelevant.

The Tragic

Here’s the tragedy: the Democrats, once the defenders of free speech, now look like the humourless school principal confiscating your slingshot. They’ve managed to become the least funny people in the room. Worse, they’ve turned the very idea of free expression into a tribal weapon—defend it when it’s mocking Republicans, cancel it when it’s mocking their own side.Jimmy Kimmel’s brief disappearance after a factually incorrect statement masquerading as joke about Charlie Kirk’s death tells you everything. The FCC flexed, networks panicked, and the once-sacrosanct First Amendment became a partisan piñata. When the shoe was on the other foot, Democrats were perfectly happy to see Conservative voices silenced. Any comedian or even person who didn’t toe the line faced what the Conservatives called Cancel Culture. Progressives spent years perfecting the tools of cancellation, and now find those tools being used on them. And the Conservatives now call it “Consequence Culture”.The tragedy isn’t just that free speech has died—it’s that it has been killed by those who once pretended to be its defenders. And ordinary Americans see it. That’s why late-night’s cultural power collapsed. People don’t want to be preached to after work. They want to laugh at absurdity, even if it’s offensive, even if it’s messy. But Democrats have forgotten that laughter thrives on risk. They’ve made humour into a sermon, where the only acceptable punchline is one that flatters their politics.And in doing so, they’ve handed the cultural high ground to a former reality TV star. That’s the tragic inversion of the American political stage: the party of supposed progressivism now looks like the Ministry of Truth, while the party of Trump—the man who once whined about being treated unfairly—sells himself as the outlaw comedian taking on the establishment. That’s not progress. That’s a Shakespearean Fool in a MAGA hats.

The Politics

Politically, the tables have turned. The Democrats once weaponised lawfare, moral grandstanding, and regulatory pressure against Trump. Today, Trump wields the exact same playbook against them and without any subtlety. He’s not innovating. He’s imitating. And in politics, imitation isn’t flattery, it’s a brutal show of force.In 2016 and 2020, Democrats turned to the courts, to the FBI. They thought they’d built a permanent arsenal against Trumpism. But Trump, the eternal student of survival, watched, learned, and adapted, and somehow figured out how to come back from the dead. Now he owns the networks, all of whom turn up – some metaphorically, some literally – to kiss his ring at the White House.A man condemned by the US political system, who felt the full brunt of federal forces, became the first President to get his own mugshot—and in typical Trumpian fashion, he sold it. What should have been a mark of shame became a badge of rebellion.This isn’t new. History is filled with such reversals. In the US, Joseph McCarthy silenced communists in the 1950s, only for campus progressives in the 2010s to silence conservatives with equal zeal. The lesson is always the same: free speech isn’t a principle; it’s a privilege handed out by whoever holds the microphone.And right now, Trump is holding the microphone. And right now, Trump is holding the microphone. But he won’t always. Gavin Newsom has begun to parody him, trolling MAGA with the same all-caps nicknames and carnival showmanship Trump perfected. From “Taco Trump” to “Just Dance Vance,” Newsom has proved Democrats can mock back — and MAGA, for once, doesn’t laugh. Trump may own the mic today, but Newsom is already testing its weight, waiting for his turn to grab it.When Jimmy Kimmel says Trump “wants me and the hundreds of people who work here fired because he can’t take a joke,” he isn’t wrong. But the point is that Trump doesn’t need to “take a joke.” He already is the joke, and he’s better at it than Kimmel. Politically, that makes him untouchable. Because in a culture where humour is more powerful than policy, the funniest man in the room usually wins.The bigger danger here isn’t Jimmy Kimmel losing his timeslot. It’s that America’s sacred ideal of free speech has been reduced to a partisan gimmick and politics is now just trolling. Conservatives and liberals now treat it like a weapon—use it when it helps, discard it when it hurts. The chorus hasn’t changed, only the choir.Kimmel’s return is symbolic. The comedian is back, but the comedy is gone. There was a time when American comedy was so space-time-culture transcending that everyone in the world could keep up with its humour. But now, to paraphrase a popular sitcom, America and mainstream comedy, are on a break. The politics has already swallowed it whole. And so, America’s funniest man isn’t paid by ABC at 11 PM—he’s in the Oval Office at 11 AM. And who’s paying for it? America and the world.