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What We Can Learn From Jon Stewart’s Monologue

by Eve Heidenry September 26, 2025 in Opinion 4 min read

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Jon Stewart, the late-night host of The Daily Show, surprised viewers when he aired on Thursday, breaking his typical routine of airing only on Monday nights. Stewart began the show and immediately addressed his audience: “We have another fun, hilarious, administration-compliant show,” with Stewart as their “patriotically obedient host,” hinting at the Trump administration’s latest moves to silence critics in the media.

Trump’s war on free speech continued as ABC suddenly pulled Jimmy Kimmel Live! due to pressure from the Trump administration and media conservatives regarding comments Jimmy Kimmel made about the assassination of far-right activist Charlie Kirk. However, Kimmel’s comments were relatively harmless, if a little tone deaf, taking a gibe at MAGA itself rather than the late Kirk, stating, “The MAGA gang [is] desperately trying to characterize this kid who murdered Charlie Kirk as anything other than one of them and doing everything they can to score political points from it.”

Stewart, like other late-night hosts, has offered support for Kimmel, sardonically praising President Trump following Kimmel’s cancellation. In a later segment of the show, Stewart interviewed Maria Ressa, a recipient of the Nobel Peace Prize in honor of her fight for free speech and democracy in the Philippines. “Americans are like deer in headlights. If you don’t move and protect the rights you have, you lose them, and it’s so much harder to reclaim them,” she said.

Stewart, admirably, is not afraid to bully Trump back. He has spent his career ardently calling out the hypocrisies of the right and has always openly dissented against Trump and his policies. At one point on Thursday, wearing a blue suit with a red tie and surrounded by a gold backdrop intended to poke fun at Trump’s Oval Office decorations and attire, he joked that “free speech is speech that supports the president.” 

He sarcastically endorsed Trump’s tantrums about recent criticisms. Noting that Trump was on a two-day state visit to the United Kingdom, Stewart stated, “If you felt a little off these past couple of days, it’s probably because our great father has not been home, for father has been gracing England with his legendary warmth and radiance,” painting Trump to be a larger-than-life and allegedly caring figure dominating the American political landscape. “You may call it free speech in jolly old England, but here in America, we have a little something called the First Amendment. And let me tell you how it works. There’s something called a talent-o-meter … that is kept on the president’s desk and it tells the president when a performer’s TQ — talent quotient — measured mostly by niceness to the president, goes below a certain level.” The show later included a song praising the president’s alleged accomplishments, intellect, and not-so-deteriorating physical appearance.

Following Kimmel’s suspension, the Trump-appointed chair of the Federal Communications Commission, Brendan Carr, threatened to take action against Disney and ABC. Carr accused Kimmel of the “sickest conduct possible” and stated that firms like Disney-owned ABC should “find ways to change conduct to take action on Kimmel.” Trump also remarked that television networks “against” him should “maybe” lose their licenses, trying to evade the free speech of his critics, which is censorship at its finest.

Stewart also slammed CBS in July for cancelling The Late Show With Stephen Colbert and denounced viewing those “whom we disagree with as somehow being less than human.” Stewart thoroughly backed Stephen Colbert and took jabs at CBS. “I understand the corporate fear. I understand the fear that you and your advertisers have with $8 billion at stake, but understand this, truly, the shows that you now seek to cancel, censor, and control — a not insignificant portion of that $8 billion value came from those [expletive] shows,” Stewart said in a fiery diatribe. “That’s what made you that money. Shows that say something, shows that take a stand, shows that are unafraid.”

Stewart’s open and relentless resistance to the Trump administration says what countless Americans are thinking, yet they feel ignored by those who refuse to stand up to Trump. The right to free speech is a cornerstone of the United States, and now that right is under attack by a movement that considers even the slightest opposition to be a threat to its legitimacy. Through relentless bullying, executive orders, and cancellations, our civil liberties are disappearing before our very eyes. For MAGA, they only care about free speech until someone says something exposing their fallacies.

Stewart is correct. True power does not come from bowing down to a growing authoritarian with a childlike temper. In a time of more social unrest than ever, the First Amendment keeps this country from falling even deeper into harmful extremist narratives. The Constitution is not merely a document full of suggestions for politicians to follow when it is convenient for them. Talk show hosts like Colbert, Kimmel, and Stewart not only make light of our current political landscape but also make it bearable to think about American politics.

The opinions expressed within this piece represent the views of the author alone and do not necessarily reflect the views of The Jefferson Independent.

Tags: featured jon stewart monologue Opinion tv

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Eve Heidenry

Eve is a third-year undergraduate at the University of Virginia, pursuing a double major in history and politics. She comes from Denver, CO, and specializes in writing about current events and legal affairs.

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