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Home Entertainment TV Show

The Perilous Stage: High-Profile Comedians Grapple with Unprecedented Challenges

September 20, 2025
in TV Show
Reading Time: 6 min

“You can’t joke about anything anymore.”

This sentiment has echoed through comedy circles for a decade, with figures like Joe Rogan and Dave Chappelle frequently discussing the perils of ‘cancel culture’ and advocating for free speech amidst backlash. Even tech mogul Elon Musk has weighed in, suggesting that comedy itself is under attack.

Yet, in a startling turn of events, Stephen Colbert’s show was canceled and Jimmy Kimmel was suspended – both prominent late-night hosts known for centering their humor on President Trump. The irony deepens as many top American comedians now look to perform in Saudi Arabia.

Next week, a roster of America’s most celebrated stand-up comedians, including Dave Chappelle, Bill Burr, and Kevin Hart, are set to appear at a major festival in Riyadh. The event, hosted by a government with a questionable record on free expression, carries particularly awkward timing given recent domestic events.

Comedian and podcaster Tim Dillon, known for his nihilistic style, recently revealed his dismissal from the Saudi festival after making controversial comments on his podcast. Dillon, who had previously bragged about a substantial payment for his performance, connected his firing to the wider issue of comedy crackdowns, specifically criticizing Kimmel’s suspension. He stated, ‘It’s wrong to pretend it’s because the show sucked or because it was losing eyeballs or money. Clearly it was a politically motivated hit job,’ appearing to target right-leaning comedians who had previously criticized Kimmel.

His frankness, at least, is noteworthy.

Both Stephen Colbert and Jimmy Kimmel had long drawn the ire of President Trump.

While it was once easy to dismiss late-night comedians’ presidential jabs as pandering, the recent events add a stark new layer to the conversation. Kimmel, in particular, was well aware of the risks involved. President Trump had publicly called for his show’s cancellation long before ABC’s suspension, illustrating a pattern of pressure against various institutions, from academia to media.

Following the cancellation of ‘The Late Show’ by CBS, a move vaguely explained as ‘purely financial’ but increasingly doubted, Stephen Colbert used his first monologue to address the situation. Responding to the president’s social media comment — ‘I hear Jimmy Kimmel is next’ — Colbert defiantly declared, ‘No, no, absolutely not Kimmel. I am the martyr. There’s only room for one on this cross.’

It seems there’s room for more. In these uncertain times, comedians face uncharted territory. The questions now loom large: How will network comics adapt to such pressures? What direction will Lorne Michaels take with ‘Saturday Night Live’’s cold open? And how will Jimmy Fallon navigate ‘The Tonight Show’?

On ‘The Late Show,’ Colbert labeled Kimmel’s situation ‘blatant censorship,’ while Fallon chose a more ambiguous path. After offering praise and wishing for Kimmel’s return, Fallon stated, ‘To be honest with you all, I don’t know what’s going on — no one does.’

Jimmy Fallon’s show has never been as politically charged as those of his fellow 11:30 p.m. hosts.

This claim of ignorance is questionable, yet understandable. Fallon has never presented himself as a political satirist burdened by artistic responsibility in an authoritarian era, nor has he shown particular interest in politics. Despite this, he inadvertently became embroiled in political controversy, notably blamed for trivializing the first Trump presidency after famously ruffling Trump’s hair in 2016. At the time, this criticism felt misplaced, as both Trump and hair jokes were long-standing elements of popular culture, and Fallon simply seemed to be going with the flow.

However, recent actions suggest Fallon might be preemptively softening his stance, aiming to sidestep administration criticism by adopting a more conciliatory tone and toning down political humor. A notable guest on ‘The Tonight Show’ was Fox host Greg Gutfeld, who, predictably, expressed little concern over Kimmel’s suspension on his own program. Yet, even Fallon’s efforts haven’t deterred criticism, with the president swiftly responding to Kimmel’s suspension by predicting Fallon would be next.

Observing comedians grapple with this challenging environment, I’m drawn to historical parallels. My thoughts return to a trip to Moscow in 2003 for an article about Russian artists staging American musicals post-Soviet Union. It was a time of cultural awakening, but also nascent caution.

Vladimir Putin had only been president for a few years, and censorship wasn’t as severe as it is now. Yet, conversations with Russian artists revealed a nascent sense of caution. One particularly striking encounter was with Philipp Kirkorov, a wildly famous and flamboyant pop singer. He was producing the cynical musical ‘Chicago’ and playing the lead role to sold-out audiences. Backstage, when I called him a ‘star,’ he corrected me through a translator, ‘I am not a star. I am a Kremlin star.’

The career of the singer Philipp Kirkorov shows what life can be like for an entertainer under an authoritarian regime.

At the time, his statement baffled me. Now, it’s clear he was signaling his loyalty to the regime, a strategic move to play it safe. In the two decades that followed, marked by Russia’s annexation of Crimea and invasion of Ukraine, nearly all the artists I interviewed have either passed away or left the country. Kirkorov, however, remained, consciously avoiding government criticism. Yet, even for a ‘Kremlin star,’ life isn’t without its challenges.

Indeed, in 2023, Kirkorov faced severe backlash from lawmakers and pro-government commentators for attending a private party with scantily clad celebrities during wartime. Photos of the event led to arrests and fines for many attendees. Kirkorov, likely due to his prominence, became a public example. His concerts were canceled, and in humiliating acts of atonement, he publicly apologized and, last year, performed for wounded Russian soldiers in a Donbas hospital.

Despite his best efforts to navigate the system, avoid war commentary, and remain apolitical, Kirkorov discovered that in an authoritarian state, politics inevitably finds its way to you.

In a peculiar cultural intersection, Jimmy Fallon dedicated a comedic segment on ‘The Tonight Show’ this May to Kirkorov. Prompted by a fan letter suggesting a resemblance, Fallon displayed a photo of the famously glittery and bushy-haired singer, then donned a wig and handlebar mustache to mimic his look.

Fallon’s impersonation garnered laughs, highlighting the perceived contrast between the clean-cut host and the flamboyant singer. However, in today’s rapidly evolving and increasingly restrictive environment for comedy and free expression, with Fallon potentially becoming the sole remaining 11:30 p.m. host, he may soon find an unsettling kinship with the ‘Kremlin star.’

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