Late-night talk shows weren’t always the sharp, politically charged platforms they are today. For decades, this uniquely American television staple featured genial hosts in suits, delivering lighthearted jokes and celebrity interviews, aiming to soothe audiences into slumber. Controversial political comedy was the domain of edgier stand-ups like Lenny Bruce, George Carlin, or Dave Chappelle. Yet, in a surprising turn, the most prominent critics of the second Trump administration—and those facing the most intense scrutiny—are the very network late-night hosts once considered establishment figures. How did these mainstream personalities become so deeply entrenched in political discourse?
Conservative critics often claim that late-night hosts retreated into a ‘liberal bubble,’ suggesting their amplified critiques of Trump stemmed from partisan bias rather than genuine commercial appeal. Conversely, others credit President Trump himself, arguing his unique ability to politicize nearly every issue naturally pushed these shows into the fray. However, neither of these explanations fully captures the complex truth.
To truly grasp how network late-night hosts became such vocal critics of Trump, we must consider the broader historical context. Their increasingly political commentary developed gradually, long before the current president. This evolution can be clearly observed through the career trajectory of Jimmy Kimmel. He transitioned from the boisterous, ‘frat-boy’ humor of ‘The Man Show’ in the early 2000s to becoming an unexpected voice of resistance, passionately advocating for free speech and journalistic integrity upon his return to television Tuesday night, following the suspension of ‘Jimmy Kimmel Live!’ by Disney under pressure from the Trump administration.
Kimmel has consistently cited David Letterman as his childhood hero, affectionately calling the veteran host ‘my Jesus.’ Many of Kimmel’s current actions echo the spontaneous irreverence towards authority that was a hallmark of ‘Late Night With David Letterman’ throughout the 1980s. This image captures a younger Jimmy Kimmel, third from the right, during his earlier career on the sketch-focused ‘Man Show.’ David Letterman, seen here with guest Teri Garr, pioneered an irreverent style on his 1980s NBC show, a comedic approach that profoundly inspired Jimmy Kimmel.
However, pinpointing a single transformative ‘Road to Damascus’ moment for Kimmel’s political awakening might be misleading. The significant political shift in late-night television, including Kimmel’s own evolution, truly began with the groundbreaking show that succeeded ‘The Man Show’ on Comedy Central: ‘The Daily Show With Jon Stewart.’ While political comedy certainly existed before Stewart — from the fiery debates 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!’ on ABC) — Stewart’s immense success spawned an entirely new breed of assertive, opinionated comedy. He wasn’t merely commenting on the news; for many viewers, he *became* their primary news source.
Stewart became a relentless satirist, targeting the Bush administration with sharp wit during the build-up to the Iraq War. Crucially, he was just as fierce in his critiques of superficial media coverage. This approach—where a host connects with an audience by disdainfully mocking political media—draws a clear parallel to how figures like Joe Rogan operate on his podcast today, often exploring alternative theories on everything from vaccines to World War II. Jon Stewart shares a moment with Barack Obama during a segment on ‘The Daily Show.’ John Oliver, a former ‘Daily Show’ correspondent, now hosts HBO’s ‘Last Week Tonight.’
Stewart nurtured a talented team of correspondents, including future hosts like John Oliver, Samantha Bee, and Stephen Colbert, establishing a pipeline for the next generation of late-night talent. His consistent victories over Conan O’Brien at the Emmy Awards, in hindsight, seemed to reflect a prevailing, though arguably misguided, notion that politically charged comedy was inherently more ambitious.
Ultimately, Stewart’s profound impact on late night stemmed from his ability to attract vast audiences, particularly younger demographics. This success prompted established hosts like Letterman to become more politically outspoken. Letterman not only engaged in memorable sparring matches with figures like vice-presidential candidate Sarah Palin but also frequently hosted an unvarnished businessman named Donald Trump, allowing him to candidly comment on current events.
Upon Letterman’s retirement, CBS appointed Colbert as his successor. After an initial struggle, Colbert truly found his stride following the 2016 election, when his monologues transitioned into more fervent and direct political commentary. He eventually achieved what Letterman never could, consistently outperforming ‘The Tonight Show’ in the annual ratings. Yet, even as a ratings leader, Colbert’s show faced financial challenges and ultimately, cancellation. Stephen Colbert, pictured here, gained significant traction after the 2016 presidential election by infusing his monologues with more impassioned news commentary. Johnny Carson, alongside his iconic sidekick Ed McMahon, captivated enormous audiences during an era when television viewers had fewer entertainment options.
Beyond political alignment, the economic foundations of talk shows crumbled, mirroring the fate of print media, primarily due to the internet. Advertising revenues plummeted, and social media platforms began delivering topical jokes long before late-night shows could. The increasing fragmentation of culture further reshaped what resonated with audiences. Johnny Carson, for instance, commanded a massive national viewership partly because there were simply fewer entertainment alternatives. Today, audiences are dispersed across countless cultural ‘silos,’ lacking shared reference points. Curiously, one of the few topics that consistently unites people of vastly different ages and backgrounds is, indeed, presidential politics.
This fragmented, politically charged landscape is the arena in which Jimmy Kimmel operates. His most acclaimed joke during his last Oscar hosting gig was an unscripted retort to a social media jab from Trump. Similarly, one of Kimmel’s most impactful monologues was a deeply personal plea for health care, delivered after his son’s emergency open-heart surgery. These moments connect with audiences because of their authenticity. While political clashes inherently attract attention, their true power lies in the genuine context from which they arise.
The era of broad, monocultural topical comedy is over. For those who harbor disdain for liberals or mainstream media, a plethora of entertainers now seamlessly blend conservative commentary with sharp mockery, ranging from Greg Gutfeld on Fox News to podcaster Steven Crowder and numerous online personalities on X. Intriguingly, this year’s stand-up comedy landscape reveals a notable absence of specials on major streaming platforms that attempt to tackle the current administration and capture the political mood of the times. Greg Gutfeld presents a conservative late-night option to viewers on Fox News. Podcaster Steven Crowder represents another voice in conservative commentary.
It remains uncertain whether this trend is due to Trump becoming a less captivating comedic subject, insufficient time having passed, or artists and executives exercising increased caution. Notably, Hulu, a prominent producer of comedy specials, is owned by the same parent company that suspended Kimmel, which could signal a challenging future for overtly political comedy within its stand-up offerings.
All these factors culminate in a vibrant market for liberal comedic critiques of power, a role increasingly embraced by late-night talk show hosts. Those who have repeatedly declared late night irrelevant might need to reconsider. Governments typically don’t target entertainers who hold no sway. Regardless of one’s opinion on Kimmel’s politics or comedic style, his monologue on Tuesday night undeniably stood out as the year’s most talked-about comedy moment.
Kimmel opened his return with a nod to late night’s history of free-spirited defiance, referencing a moment likely lost on much of his audience. He quoted the inaugural line spoken by ‘Tonight Show’ host Jack Paar in 1960, upon his return after a dramatic mid-show walkout: ‘As I was saying before I was interrupted.’ Paar’s original protest, however, stemmed from a less nationally significant act of network censorship: a simple reference to a toilet.
It’s worth recalling that Trump himself was a frequent and enthusiastic guest on network talk shows for decades. Therefore, in a peculiar twist of fate, perhaps only he possessed the unique ability to achieve the seemingly impossible: truly ‘Make late-night great again’ by sparking its political resurgence.