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Home Entertainment TV Show

Beyond Trump: Unpacking Late-Night’s Deep Roots in Political Comedy

September 24, 2025
in TV Show
Reading Time: 6 min

Late-night talk shows weren’t always known for their sharp political edge.

For most of its history, this uniquely American genre featured affable Midwestern hosts in suits, offering apolitical jokes and celebrity interviews to wind down the evening. Controversial comedians tackling societal issues were typically stand-ups like Lenny Bruce, George Carlin, or Dave Chappelle. Yet, today, the most prominent critics of the current administration — and the ones facing the most scrutiny — are the very network late-night hosts once considered part of the establishment. How did these figures become so deeply entrenched in political commentary?

Some conservatives have suggested that late-night hosts became isolated in a liberal echo chamber, with their critiques of Trump driven by political leanings rather than commercial appeal. Others attribute the politicization solely to the former President, who has a knack for turning every aspect of public life into a political battleground. However, neither explanation tells the full story.

To truly understand late-night hosts’ critical stance against Trump, we must consider the broader historical context. Their increasingly political commentary began long before his presidency and evolved gradually. Jimmy Kimmel’s career offers a clear illustration of this transformation, evolving from the ‘frat-boy’ humor of “The Man Show” in the early 2000s to his current role as an unexpected champion of free speech and journalistic integrity. This journey was highlighted by his recent return to television, following a suspension of his ABC show, “Jimmy Kimmel Live!,” amid pressure from the administration.

Kimmel’s most significant influence has always been his childhood idol, David Letterman, whom he once affectionately called “my Jesus.” Many of Kimmel’s current actions reflect the spontaneous irreverence toward authority that “Late Night With David Letterman” frequently demonstrated in the 1980s.

However, focusing solely on Kimmel’s personal journey overlooks a crucial catalyst. The broader political shift in late-night television, including Kimmel’s own, truly accelerated with Jon Stewart’s groundbreaking program, “The Daily Show,” on Comedy Central. While political comedy had graced late-night before Stewart—from heated discussions on “The Dick Cavett Show” in the ’60s and ’70s to Bill Maher’s “Politically Incorrect” in the ’90s (ironically replaced by “Jimmy Kimmel Live!”)—Stewart’s success ushered in a new era of socially conscious humor. He didn’t just comment on the news; for many, he became a primary source of it.

Stewart relentlessly parodied the Bush administration in the lead-up to the Iraq War, but he was equally sharp in his persistent mockery of superficial media coverage. This approach—connecting with viewers by deriding political media—can be seen as a direct predecessor to how figures like Joe Rogan engage their podcast audience before delving into unconventional theories on various topics.

Stewart also nurtured a talent pool of correspondents, including John Oliver, Samantha Bee, and Stephen Colbert, who went on to become successful talk-show hosts themselves. Stewart’s consistent victories over Conan O’Brien at the Emmy Awards, in hindsight, hinted at a growing appreciation for politically charged comedy as a more ambitious form.

Ultimately, Stewart’s enduring impact on late night stems from his ability to attract large audiences, especially younger demographics. This success prompted established hosts like Letterman to become more politically outspoken. Letterman not only engaged in feuds with figures like vice-presidential candidate Sarah Palin but also regularly invited an unfiltered businessman named Donald Trump to offer his takes on current events.

After Letterman’s retirement, CBS appointed Colbert as his successor. Colbert initially struggled but found his voice after the 2016 election, delivering more passionate news commentary. He eventually outpaced “The Tonight Show” in ratings year after year, a feat Letterman couldn’t achieve. Despite his ratings dominance, Colbert’s show, however, eventually faced cancellation.

Beyond political considerations, the economic model for talk shows suffered the same fate as print media: the rise of the internet. Advertising revenues plummeted, and social media offered instant topical jokes, often before late-night shows could. The increasing fragmentation of culture also altered what resonated with audiences. Johnny Carson once captivated a vast national audience in part because viewers had limited alternatives. Now, audiences are segmented into cultural silos, lacking shared reference points. Ironically, one of the few subjects that reliably unites people across diverse ages and backgrounds is presidential politics.

This is the competitive landscape Jimmy Kimmel navigates. His most memorable joke at a recent Oscars ceremony was an impromptu comeback to a social media insult from Trump. One of Kimmel’s most moving monologues was a heartfelt plea for healthcare reform, delivered after his son underwent emergency open-heart surgery. These moments resonate because of their authenticity; while political conflict consistently draws attention, such profound moments arise within a distinct context.

The era of broad, topical comedy for a monoculture is over. For those who dislike liberals or mainstream media, there’s no shortage of performers blending conservative commentary with satire, from Greg Gutfeld on Fox News to podcaster Steven Crowder and countless online accounts. What’s particularly notable in stand-up comedy this year is the scarcity of specials on major streaming platforms that attempt to engage with the current administration and capture the political mood.

It remains unclear whether this is due to Trump becoming a stale subject, insufficient time passing, or artists and executives exercising caution. Interestingly, Hulu, a major producer of specials, is owned by the same company that suspended Kimmel. This situation raises questions about the future of political comedy in their stand-up offerings.

All of these factors combine to create a fertile ground for liberal comedic critiques of power, a role that late-night talk show hosts have readily embraced. Those who relentlessly claimed that late night was irrelevant will need to reconsider. Governments don’t target entertainers who are inconsequential. Regardless of your views on Kimmel’s politics or humor, his monologue on his Tuesday return was undeniably the comedy event of the year.

He opened with a subtle nod to late night’s history of free-spirited defiance, likely lost on much of his audience, by quoting the first line spoken by “Tonight Show” host Jack Paar in 1960 upon his return after an abrupt walk-out: “As I was saying before I was interrupted.” Paar’s original protest against network censorship, however, concerned a less weighty matter: a joke about a toilet.

Let’s not forget that Trump himself appeared on network talk shows for decades, often relishing his guest appearances. Perhaps, then, it’s a fitting paradox that only he could achieve the seemingly impossible: to make late-night television truly relevant and impactful once again.

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