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Home Entertainment TV Show

The Untold Story of Late-Night Comedy’s Political Awakening Before Trump

September 25, 2025
in TV Show
Reading Time: 9 min

Late-night talk shows weren’t always the sharpest critics.

For much of their existence, these quintessential American programs featured genial, well-dressed hosts who aimed to soothe audiences with harmless jokes and celebrity interviews. The real troublemakers, the comedians sparking debate with provocative topics, were typically stand-up artists like Lenny Bruce, George Carlin, or Dave Chappelle. Yet, in a fascinating twist, the most prominent and criticized voices against the current administration are now the very network late-night hosts once considered conventional. How did these mainstream personalities become such potent political commentators?

Some conservatives contend that late-night hosts have become isolated in a liberal echo chamber, driven by political agendas rather than viewership. Others suggest that the former president himself, with his unique ability to politicize any topic, is the catalyst. The truth, however, is more nuanced than either of these explanations.

To grasp the transformation of network late-night hosts into vocal critics, we must consider the broader historical context. This shift towards political commentary didn’t suddenly appear with the current president; it evolved gradually. Jimmy Kimmel’s career offers a prime example, spanning his early days with the raucous humor of “The Man Show” in the early 2000s to his emergence as an unexpected champion of free speech and journalistic integrity. His recent return to television, following a suspension of “Jimmy Kimmel Live!” under pressure from the administration, highlights this striking evolution.

Jimmy Kimmel in a tuxedo waves at the Emmy Awards.
Jimmy Kimmel at the Emmy Awards in 2022. He recently returned to his show after a suspension stemming from pressure by the Trump administration. Credit: Chris Delmas/Agence France-Presse — Getty Images

Kimmel has always drawn significant inspiration from his childhood idol, David Letterman, whom he affectionately once called “my Jesus.” Many of Kimmel’s present actions echo the instinctive irreverence towards authority that was a hallmark of “Late Night With David Letterman” in the 1980s.

A promotional image for 'The Man Show,' featuring Jimmy Kimmel in the background among cheerleaders.
Jimmy Kimmel, positioned third from the right in the back, first gained recognition through the sketch-driven program “The Man Show.” Credit: Jeff Kravitz/FilmMagic
David Letterman with guest Teri Garr on his 1980s NBC show.
David Letterman, seen here with guest Teri Garr, pioneered an irreverent style on his 1980s NBC show that became a significant inspiration for Kimmel. Credit: Paul Drinkwater/NBCU Photo Bank/NBCUniversal, via Getty Images

However, searching for a single “aha!” moment in Jimmy Kimmel’s political awakening might be misleading. The true political turning point for late-night television—and for Kimmel himself—can be largely attributed to the highly influential show that followed “The Man Show” on Comedy Central: “The Daily Show With Jon Stewart.” While political comedy had certainly existed before Stewart, from the fiery discussions on “The Dick Cavett Show” in the 60s and 70s to Bill Maher’s “Politically Incorrect” in the 90s (which, coincidentally, was replaced by “Jimmy Kimmel Live!” on ABC), Stewart’s groundbreaking success ushered in a new era of impactful, righteous comedy. He transcended mere commentary, becoming a de facto news source for many.

Stewart famously lampooned the Bush administration during the lead-up to the Iraq War, but he was equally critical of superficial media coverage. A clear lineage connects Stewart’s method of connecting with his audience by satirizing political media to how a figure like Joe Rogan engages listeners on his podcast before delving into alternative theories on topics like vaccines or World War II.

Jon Stewart interviewing Barack Obama on 'The Daily Show.'
Jon Stewart converses with Barack Obama on “The Daily Show.” Credit: Evan Vucci/Associated Press
John Oliver at his desk on 'Last Week Tonight.'
John Oliver transitioned from “The Daily Show” to hosting “Last Week Tonight.” Credit: Lloyd Bishop/HBO, via Associated Press

Stewart famously mentored a cohort of talented correspondents, including John Oliver, Samantha Bee, and Stephen Colbert, many of whom went on to become prominent talk-show hosts themselves. His consistent Emmy wins over Conan O’Brien, in hindsight, perhaps hinted at a growing, though perhaps misguided, preference for politically charged comedy as the more ambitious form.

However, the most significant impact of Stewart’s tenure was his ability to attract large audiences, particularly younger demographics. This success spurred other hosts, like Letterman, to become more overtly political. Letterman not only engaged in contentious interviews with figures like then-vice presidential candidate Sarah Palin but also frequently hosted an unvarnished businessman named Donald Trump, allowing him to share his unfiltered opinions on current events.

Upon Letterman’s retirement, CBS chose Stephen Colbert as his successor. Colbert initially struggled but truly found his voice after the 2016 election, transforming his monologues into fervent political commentary. This new approach allowed him to achieve what Letterman couldn’t: consistently outperforming “The Tonight Show” in the ratings. Yet, even as a ratings leader, Colbert’s show ultimately faced financial challenges and cancellation.

Stephen Colbert standing in front of his Late Show desk.
Stephen Colbert gained confidence and a stronger voice after the 2016 presidential election, when his monologues evolved into more impassioned news commentary. Credit: Scott Kowalchyk/CBS Entertainment
Johnny Carson and Ed McMahon on 'The Tonight Show.'
Johnny Carson, accompanied by his iconic sidekick Ed McMahon, commanded a massive audience during a time when viewers had limited entertainment options. Credit: Bettmann/Getty Images

Beyond political shifts, the economic foundations of talk shows crumbled, mirroring the struggles of print media: the rise of the internet. Advertising revenue plunged, and social media quickly outpaced late-night shows in delivering timely jokes. The increasing fragmentation of culture also redefined what truly resonated with audiences. Iconic figures like Johnny Carson once captivated immense national audiences, partly because television options were scarce. Today, audiences are fractured into distinct cultural groups, often lacking shared reference points. Interestingly, one of the few topics that consistently unites people across diverse ages and backgrounds remains, perhaps inevitably, presidential politics.

This is the challenging landscape Jimmy Kimmel navigates. His most memorable joke from his last Oscar hosting gig was an unscripted retort to a social media jab from the former president. Similarly, one of his most powerful monologues on his talk show was a deeply personal plea for healthcare, delivered after his son’s emergency open-heart surgery. These impactful moments connect with audiences because of their raw authenticity. While political clashes have always captured attention, these instances stand out due to their profound, real-world context.

The days of topical comedy catering to a unified, broad audience are behind us. For those who harbor disdain for liberals or mainstream media, there’s a wealth of entertainers blending conservative views with satire, including Greg Gutfeld on Fox News, independent podcaster Steven Crowder, and numerous online personalities. Intriguingly, this year’s stand-up comedy landscape reveals a notable absence: very few specials on major streaming platforms have even attempted to tackle the current administration or capture the prevailing political mood.

Greg Gutfeld smiling behind his 'Gutfeld!' desk.
Greg Gutfeld provides a conservative late-night option for viewers on Fox News. Credit: Amy Lombard for The New York Times
Steven Crowder speaking into a microphone with an American flag in the background.
Steven Crowder, a prominent podcaster, represents another voice in conservative commentary. Credit: Nicole Hester/Ann Arbor News, via Associated Press

It’s uncertain whether this trend stems from the former president becoming a less compelling subject, insufficient time having passed, or a deliberate caution from artists and executives. Notably, Hulu, a major platform for comedy specials, is owned by the same company that recently suspended Kimmel. This development raises questions about the future of political comedy within the platform’s stand-up offerings.

Collectively, these factors create a fertile ground for liberal comedic commentary on power, a space that late-night talk show hosts have readily occupied. Those who continuously dismiss late-night’s relevance may need to reconsider. Governments don’t target entertainers unless they perceive them as influential. Regardless of one’s views on Kimmel’s politics or comedic style, his recent Tuesday night monologue was undeniably the comedic highlight of the year.

Kimmel initiated his return by honoring the tradition of rebellious spirit in late-night, citing the very first words spoken by “Tonight Show” host Jack Paar in 1960. Paar’s famous line, “As I was saying before I was interrupted,” marked his return after a dramatic on-air walkout, a protest against network censorship over something as seemingly trivial as a toilet reference.

It’s worth recalling that the former president himself was a frequent and enthusiastic guest on network talk shows for decades. In a strange twist of irony, perhaps only he could inadvertently achieve the seemingly impossible: making late-night relevant and impactful once more.

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