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Home Entertainment TV Show

Late-Night TV’s Political Awakening: It Started Long Before Trump

September 24, 2025
in TV Show
Reading Time: 9 min

Once upon a time, late-night talk shows weren’t the sharpest tools in the shed for political commentary.

For generations, these uniquely American programs featured congenial hosts in suits, delivering harmless jokes and engaging in celebrity banter, designed more to soothe viewers into slumber than spark debate. The true provocateurs of comedy were stand-ups like Lenny Bruce, George Carlin, or Dave Chappelle, who dared to tackle contentious topics. Yet, today, it’s the seemingly conventional network late-night hosts who stand as the most prominent — and most scrutinized — critics of political figures. How did these mainstream personalities transform into such outspoken political voices?

Some conservatives contend that late-night hosts retreated into an echo chamber of liberal thought, their strong critiques driven purely by ideology rather than audience appeal. Others suggest that the political shift is simply a reflection of the figures themselves, especially as a former President had a knack for politicizing every aspect of public life. However, neither of these perspectives fully captures the nuanced reality.

To truly grasp how network late-night became such a powerful voice against political figures, we need to consider a broader historical context. The genre’s increasing political engagement wasn’t a sudden event but a gradual evolution that predates recent administrations. A prime example of this transformation is Jimmy Kimmel. He began his career with the boisterous, ‘frat-boy’ humor of ‘The Man Show’ in the early 2000s. Fast forward, and he has remarkably morphed into an unexpected champion of free speech and journalistic integrity, a role he embraced upon his return to television after his show faced suspension due to political pressure.

A bearded man in a tuxedo waves.
Jimmy Kimmel, captured here at the 2022 Emmy Awards, made a much-anticipated return to his talk show after its suspension, a move that came after considerable pressure from a past administration.

Kimmel’s deep admiration for his childhood idol, David Letterman—whom he famously once called ‘my Jesus’—has profoundly shaped his career. Many of Kimmel’s current actions echo the spontaneous, anti-establishment spirit that Letterman’s ‘Late Night’ show consistently embodied throughout the 1980s.

Surrounded by women in cheerleader outfits emblazoned with the title “The Man Show,” a man in an open-collar shirt stands at the back, next to another man.
In an early career highlight, Kimmel is seen here, third from the right in the back, during his formative years on the sketch-comedy-driven ‘Man Show.’
A smiling man in a suit sits behind a desk with a microphone. Next to him on a chair is a woman in a purple dress.
David Letterman, pictured here with guest Teri Garr, pioneered an irreverent style on his 1980s NBC show, a comedic blueprint that would deeply inspire Kimmel’s own career.

However, pinpointing a single transformative moment for Jimmy Kimmel’s political awakening might be too simplistic. The real catalyst for late-night television’s—and Kimmel’s—political evolution came with the highly influential show that succeeded ‘The Man Show’ on Comedy Central: ‘The Daily Show With Jon Stewart.’ While political humor had certainly appeared on late-night TV before Stewart, from fiery segments 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 groundbreaking success inaugurated a fresh era of insightful, often scathing, political comedy. He didn’t merely react to the news; for many viewers, he became an indispensable alternative news source.

Stewart’s sharp wit was aimed squarely at the Bush administration in the lead-up to the Iraq War, but he was equally unsparing in his critiques of superficial media reporting. His method of connecting with audiences through a shared disdain for political media’s shortcomings draws a clear parallel to how some modern podcasters engage their listeners, even when discussing controversial topics like alternative theories on health or history.

On a set with a global map in blue behind them, two men in suits sit across from each other. One is laughing and the other is gesturing.
Jon Stewart, pictured here with Barack Obama on ‘The Daily Show,’ pioneered a style of political comedy that resonated deeply with viewers.
A man in a suit with a plaid shirt sits at a desk with a skyline behind him.
John Oliver transitioned from his role on ‘The Daily Show’ to become the acclaimed host of ‘Last Week Tonight,’ continuing the tradition of in-depth political satire.

Stewart fostered a remarkable talent pool, with correspondents like John Oliver, Samantha Bee, and Stephen Colbert eventually launching their own successful talk shows. Historically, Stewart’s consistent victories over Conan O’Brien at the Emmy Awards perhaps highlighted a prevailing notion that political comedy carried more prestige.

However, Stewart’s most profound impact on late-night was his ability to attract vast audiences, particularly younger demographics. This success spurred other hosts, including Letterman, to become more overtly political. Letterman, for instance, not only engaged in memorable sparring matches with figures like Sarah Palin but also frequently welcomed a then-unfiltered businessman, Donald Trump, to share his unfiltered opinions on current events.

Following Letterman’s retirement, Stephen Colbert took over the CBS slot. After an initial struggle, Colbert truly hit his stride post-2016 election, transforming his monologues into passionate, timely commentaries. He achieved what Letterman hadn’t: consistently outranking ‘The Tonight Show’ in ratings. Yet, even as a ratings leader, Colbert’s program eventually faced financial challenges and cancellation.

A man in a suit stands with hands in pocket in front of a desk with a logo reading “Late Show.”
Stephen Colbert, seen here, found his distinctive voice and audience after the 2016 presidential election, transforming his nightly monologues into sharp, emotionally charged political commentary.
A man in a dark suit and tie sits behind a desk gesturing. On the couch next to him is a smiling man in a light-colored suit.
Johnny Carson, alongside his beloved sidekick Ed McMahon, commanded an enormous television audience in an era when viewers had far fewer entertainment options.

Beyond political leanings, the fundamental business model for talk shows faced a similar collapse to that of print media: the internet. Advertising revenues plunged, and social media platforms delivered instant topical jokes, often before late-night shows could. Furthermore, cultural fragmentation meant that Johnny Carson’s ability to captivate a broad national audience, largely due to limited viewing options, was a relic of the past. Today, audiences are segmented into countless cultural ‘silos,’ with few shared reference points. Ironically, one of the few topics that consistently unites people across diverse ages and backgrounds is, you guessed it, presidential politics.

This is the challenging landscape Jimmy Kimmel navigates. His most memorable moment from his last Oscar hosting gig wasn’t scripted, but an unscripted retort to a social media jab. Similarly, one of his most impactful monologues was a heartfelt, personal plea for healthcare access, delivered after his son’s emergency surgery. These instances resonate deeply because of their authenticity. While political clashes reliably attract viewership, such genuine, personal moments also underscore the evolving role of late-night commentary.

The age of broad, monocultural topical comedy is behind us. For those who lean conservative or distrust mainstream media, there’s an abundance of entertainers offering right-leaning commentary infused with satire, ranging from cable news hosts like Greg Gutfeld to independent podcasters and numerous online personalities. Interestingly, this year’s stand-up comedy landscape on major streaming platforms shows a noticeable scarcity of specials that directly engage with the current political administration or aim to capture the prevailing political mood.

A grinning man in a dark suit sits on a light-colored chair. Behind him is a skyline with the logo “Gutfeld!” affixed to it.
Greg Gutfeld, a host on Fox News, provides a distinct conservative late-night alternative for viewers.
With an American flag blurred in the foreground, a bearded man in a dark top stands nearby, holding a microphone to his mouth.
Steven Crowder, a prominent podcaster, represents another voice in conservative commentary.

It’s uncertain whether this trend reflects a fatigue with political figures as a comedic subject, insufficient time for artists to process recent events, or a heightened sense of caution from creators and executives. Notably, the major platform producing many comedy specials is owned by the same parent company that previously suspended Kimmel’s show. This raises questions about the future landscape for politically charged stand-up comedy on such platforms.

Collectively, these factors have created a receptive environment for liberal comedic commentary on power, a space that late-night talk show hosts have readily occupied. Those who continually dismiss the relevance of late-night television would do well to reassess. Governments typically don’t target entertainers who are irrelevant. Regardless of one’s opinion on Kimmel’s political stances or comedic style, his recent monologue was undeniably a standout comedic event, commanding significant attention.

His memorable monologue opened with a subtle nod to the historical spirit of defiance within late-night, a reference likely lost on many viewers. He quoted Jack Paar, host of ‘The Tonight Show,’ upon his return in 1960 after famously walking off set: ‘As I was saying before I was interrupted.’ Paar’s abrupt departure was, rather anticlimactically, a protest against network censorship over a joke about a toilet.

It’s worth noting that a former President was a frequent and enthusiastic guest on network talk shows for decades. Perhaps, then, there’s a certain irony in the idea that he might inadvertently be the one to achieve the seemingly impossible: revitalizing late-night television.

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