Top 30 Legendary Jon Stewart Moments on TV

#30: “Praising” Trump After Kimmel Scandal (2025)

“The Daily Show” (1996-)

With an ongoing debate about the 1st amendment, Jon Stewart is here to make you laugh through the tears. His show decided to take aim at the Jimmy Kimmel scandal in a completely different way. Adorning the studio with gold, Stewart hopes to impress President Trump with a change in decor. He uses the segment to pretend to act afraid and garner sympathy from the commander-in-chief. It’s all played for laughs, with an adept and satirical take on the current media landscape. While it’s rooted in some genuine fears, this episode finds a way to dissect a hot-button topic that deserves analysis.

#29: Jon Surprises Jimmy Kimmel’s Kids (2024)

“Jimmy Kimmel Live!” (2003-)

After he picked up Olivia Rodrigo on the side of the road, Jimmy Kimmel brought someone else on the morning commute. Jon Stewart later hitched a ride with the ABC host’s unimpressed children. Most of the comedy comes from the confusion and awkwardness of the encounter. The “Daily Show” host is able to find the laughs, while also not leaning on his fame too much. It’s an all-around fascinating look at the generation gap and the evolution of the funny man’s influence. At the very least, this is also a fun excuse to get the “Daily Show” presenter in a car with the family.

#28: Finding Jon in a Log Cabin (2016)

“The Late Show with Stephen Colbert” (2015-)

After Jon Stewart left “The Daily Show” in 2015, he wasn’t done talking about issues or the state of America. His friend Stephen Colbert allowed him to appear on “The Late Show with Stephen Colbert” more than a few times. This time around, Colbert ventures deep into the woods to find his old buddy in a log cabin. It’s at this location that Stewart provides some satirical support to the “Late Show” presenter. While the cabin dweller does a spit take, he also brings out some much-needed help to react to Donald Trump. Segments like these helped fans cope with his momentary TV absence.

#27: Crashing Conan’s Show & Leaving (2011)

“Conan” (2010-21)

Along with having a friendly rivalry with other co-hosts, Jon Stewart shows up to support some of his competition. He happened to make one such appearance when Conan O’Brien did his show in New York. Stewart appeared in the audience as just another fan, with a joke about having a ticket. He messes around with O’Brien in a funny exchange. In a bit about having to go film his own program, the “Daily Show” host runs off before another comedian takes his place. It’s fun to watch this kind of interplay between people who could’ve easily avoided one another.

#26: Hitting John Cena with a Chair

“The 28th Annual SummerSlam” (2015)

This comedian doesn’t immediately strike you as someone that could wrestle. Despite that, Jon Stewart has some hidden talents in the ring. When he joined “SummerSlam” in 2015, he postponed his beef with Seth Rollins and became one of John Cena’s fiercest competitors. This includes an unexpected stunt with a chair. Even if you’re a wrestling fan, you might find this to be an entertaining match full of surprises. Stewart makes himself known in a shocking move that’ll have you cheering. While he’s more known for his comedic ways, the presenter also knows how to draw a crowd and get an audience hyped up. Maybe he’s a WWE superstar in the making after all.

#25: Responding to Colbert’s Cancellation (2025)

“The Daily Show” (1996-)

Longtime friends and supporters, Jon Stewart and Stephen Colbert have been allies since their collaboration on “The Daily Show.” That makes this particular segment about Colbert’s “Late Show” ending even more meaningful. Stewart stands up for his friend in the face of what seems like corporate overreach. Unafraid of being censored or the decisions of CBS, Stewart and his solidarity here make for an important piece of pop culture history. The host lets his opinion be known and he doesn’t hold back either in a rousing musical segment. He’s able to mix comedy and a serious anti-censorship message, with a gospel choir bringing it all home.

#24: Judith Miller Interview (2015)

“The Daily Show” (1996-)

If you’ve watched “The Daily Show” over the years, you’ll know how Jon Stewart feels about America’s time in the Middle East. This interview brings some of his feelings full circle. Welcoming Judith Miller to the show, the comedian asks the journalist about her reporting during the early 2000s. This includes allegations that she helped to sell the Iraqi conflict to the American people. Miller goes on the defensive as Stewart asks her tough questions about her past. What could’ve been a basic exchange about a book becomes a more nuanced discussion about journalism in the 21st-century.

#23: Questioning Authority

During a symposium, Jon Stewart asked some pointed budgetary questions to Deputy Secretary of Defense Kathleen Hicks. The inquiries bring out a more hostile response than he might’ve imagined. Instead of going easy on her, the interviewer decides to offer the government official some constructive criticism. Her responses fail to satisfy, with the comedian hoping to find a real answer at some point. The presenter stays the course despite some ambiguous replies. Unfortunately, the interviewee remains guarded about the discussion. It’s notable that it took the “Daily Show” host to grill a powerful person about the possible mismanagement of funds.

#22: Honoring Bruce Springsteen (2009)

“The 32nd Annual Kennedy Center Honors” (2009)

To honor Bruce Springsteen at the Kennedy Center, Jon Stewart gave a hilarious speech about the artist. This included some great jokes about the singer’s influences and roots in New Jersey. It’s clear that Stewart admires the artist and sees himself as a kindred spirit from the same state. The “Daily Show” host knows how to mix his real feelings with plenty of funny moments and heartfelt anecdotes. Considering that the musician later paid tribute to the comedian on the latter’s show, this feels like this is the beginning of an artistic bond. We could only hope for the same kind of speech at our wedding, funeral, or tribute show.

#21: Fighting Stephen Colbert & Conan O’Brien (2008)

“Late Night with Conan O’Brien” (1993-2009)

In the middle of a writer’s strike, talk show hosts needed another way to entertain audiences. This led to an ingenious and wild conflict between three late-night greats. It turns out that an argument about Mike Huckabee prompted a staged conflict on a massive scale. When Colbert and Stewart appear on O’Brien’s show, the three men engage in an all-out brawl. They might not be born fighters, but they make up for it with exaggerated looks and pure dedication. Let’s just say that the extra punches and a few falls really make it that much more special.

#20: George Carlin Interview (2004)

“George Carlin: 40 Years of Comedy” (1997)

It should come as no surprise that Stewart has cited legendary comedian George Carlin as an influence. Both he and the late Carlin are famous for using their wit - and words - to point out hypocrisy from those in power and other societal issues. In 1997, Stewart hosted this special honoring Carlin and his career. He also sat down with him for an interview, which provided invaluable insight into one of the greatest comedic minds of all time. Stewart is clearly enthralled to be in the presence of one of his idols. But he also knows how to ask pointed questions that inspire meaningful responses. As both a comedian and an interviewer, Stewart has clearly learned from the best.

#19: “Cheney's Got A Gun” (2006)

“The Daily Show” (1996-)

In 2006, then-Vice President Dick Cheney accidentally shot attorney Harry Whittington during a quail hunt. Naturally, late-night talk show comedians jumped on this incident. But it’s Stewart’s take that’s truly worth preserving. Before diving in, he gives thanks for what is sure to be a comedy goldmine. But Stewart doesn’t just rely on the absurdity of the incident for laughs. He also finds other layers, such as questioning the concept of the hunting expedition in question. He also deftly ribs the V.P.’s behavior in the aftermath, before leaving parents watching at home with some invaluable wisdom.

#18: “Indecision 2004” (2004)

“The Daily Show” (1996-)

Stewart’s tenure hosting “The Daily Show” was full of highlights from beginning to end. But arguably, he was at the height of his powers during the 2004 U.S. presidential election. Stewart and his equally-hilarious correspondents offered the perfect skewering of that year’s political contest and the various players involved, including incumbent President George W. Bush and Democratic challenger Senator John Kerry. And what ensued was much-watch television that still holds up two decades later. This coverage, equal parts informative and uproarious, earned Stewart’s “Daily Show” its second Peabody Award. Making political satire this funny is serious business.

#17: “Bush v. Bush” (2003)

“The Daily Show” (1996-)

If there’s one area in which Stewart particularly excels, it’s in pointing out hypocrisies, particularly those from elected officials. In this segment from 2003, Stewart uses video evidence to show the contrasts between George W. Bush the presidential candidate and George W. Bush the President. Namely, he points out how the 43rd President did and said things that contradicted statements made on the road to the White House. Bush is obviously not the first nor the last politician to not live up to their words on the campaign trail. But the clever editing and Stewart’s commitment to the bit make this a masterful demonstration of his abilities.

#16: Defending Trans Rights (2022)

“The Problem with Jon Stewart” (2021-23)

In the second season premiere of his Apple TV+ show, Stewart addressed the ongoing moral panic regarding issues of gender, particularly trans rights. He alludes to his own history of making insensitive jokes on the subject while also demonstrating growth since then. The best part of the episode comes towards the end, as Stewart sits down with Arkansas attorney general Leslie Rutledge to talk about a ban on gender-affirming care for trans youth. Stewart has clearly done his homework, as he cuts through Rutledge's claims with strong counter-arguments. While there’s plenty of misinformation about the trans community, we’re grateful to have Stewart standing up for truth and compassion.

#15: First Interview with Barack Obama (2010)

“The Daily Show” (1996-)

Jon Stewart had interviewed both former Presidents and Presidential hopefuls in the past, but the prospect of interviewing a sitting President always seemed too far away. That is, until President Obama agreed to an interview in October of 2010. Obama had appeared on the show before, but the stakes were very clearly different this time around. Stewart held the President’s feet to the fire, contrasting the campaign of hope he ran on with the results of his first two years in Washington. The interview showed how much Stewart’s position in the media landscape had shifted since he started, and that he was able to stand toe to toe with the most powerful man in the world.

#14: Trump Pizza Rant (2011)

“The Daily Show” (1996-)

When former Alaskan Governor Sarah Palin came to the Big Apple to meet with future President of the United States Donald Trump, Stewart was initially pleased at their choice of meal: New York pizza. He became skeptical, though, when The Donald took her to a run-of-the-mill pizza place. Strike two came when it was revealed that Trump stacks his slices on top of each other. The final blow came when “True New Yorker” Donald Trump was filmed eating his pizza with a fork. This led to a rant for the ages from Jon, validating the sacred item that is New York pizza, and even questioning Trump’s claim of being a true New Yorker.

#13: Conservative Libertarian [aka Burning Glenn Beck] (2010)

“The Daily Show” (1996-)

Republican pundit Glenn Beck moved to Fox News from HLN in 2009, and his visibility skyrocketed despite some questionable views and actions. Stewart, meanwhile, found the animated Conservative a target ripe for parody. Through a series of segments over the course of Beck’s run on Fox News, Stewart performed a pitch perfect impression of Beck’s crazy mannerisms and outlandish theories. The impression reached its peak with “Conservative Libertarian,” where Jon attempted to connect Progressivism to everything from Nazism to Bert from “Sesame Street,” using printed pictures and blackboards. Despite the massive praise the segments received, Jon never did performance art of this scale on the show again, proving Beck was truly a one-of-a-kind figure – for better or worse.

#12: “You Don’t Own This Country” (2016)

“The Late Show with Stephen Colbert” (2015-)

After a crazy week involving the resignation of Roger Ailes from Fox News and the Republican National Convention, Stephen Colbert wished for someone to share his emotions with. Luckily, Jon Stewart emerged from under Colbert’s desk and asked to get something off his chest. From there, he embarked on an epic rant railing against the Republican Party, Fox News and Donald Trump for the mess that took place in Cleveland that week. It concluded with an emotionally charged tirade that told the Right that they don’t and never have owned America. It was a brief, but fantastic, return to what made Jon famous, and he thankfully made subsequent appearances on “The Late Show” once the Trump Administration began.

#11: Owning Jim Cramer (2009)

“The Daily Show” (1996-)

Following a week of Jon bashing CNBC for their failure to warn consumers of the 2008 financial crisis, “Mad Money” host Jim Cramer came on the show after speaking out against Jon’s criticism of the network. While the interview started off civil, Stewart ultimately tore into Cramer, asking him what he thought the purpose of CNBC should be, and even exposing his own hypocrisy by playing clips of him from a 2006 interview. These clips were responsible for inducting the phrase, “Roll 212,” into “The Daily Show” lexicon, basically as code for “Your career is over.” Stewart was praised for his passion and integrity during the interview, even though it didn’t really affect Cramer.

#10: Discussing Gun Laws (2023)

“The Problem with Jon Stewart” (2021-23)

An issue as contentious as gun policy in America inspires some very heated opinions. So, it makes total sense for Stewart to cover it. Speaking with Oklahoma State Senator and gun proponent Nathan Dahm, Stewart delves into this fierce debate. Addressing the rise in gun-related deaths, he points out that the argument that wider availability of guns leads to increased safety doesn’t hold water. Without demonizing responsible gun owners, Stewart shrewdly argues for sensible regulations and how they would help protect people. He may have not changed Dahm’s mind. But he sure gave him a lot to think about.

#9: “Daily Show” Return (2024)

“The Daily Show” (1996-)

When it was announced that Stewart would be temporarily returning to host “The Daily Show” every Monday, the excitement was palpable. But with this anticipation came some questions, namely, had he lost his touch at all? Such fears were quickly assuaged as Stewart effortlessly resumed the role he had nearly a decade ago. Talking about the likely rematch for the presidency between current President Biden and former President Trump, Stewart airs his frustration in the way only he can. In his first episode back, Stewart reminded us exactly why he’s inspired such a passionate following.

#8: “Rally To Restore Sanity And/Or Fear” (2010)

Though Stewart's brand of political comedy is full of takedowns against influential figures, he cares more about meaningful change in discourse than scoring points over anyone. This was underlined by the Rally To Restore Sanity And/Or Fear, a rally hosted by Stewart and Stephen Colbert's conservative alter-ego. Designed to push back against inflammatory rhetoric, this rally drew massive coverage and a massive crowd to Washington D.C.’s National Mall, with an estimated crowd size of 215,000 people. Plenty of other stars appeared at the rally, but it was still Stewart who shined brightest of all.

#7: Owning Bill O’Reilly

“The O’Reilly Factor” (1996-2017)

Despite Fox News being one of the main targets of “The Daily Show,” Jon Stewart and Bill O’Reilly always managed to maintain a civil, if competitive, relationship. The two appeared on each other’s shows several times, but the best moments were when Stewart was on O’Reilly’s turf. There, the two debated everything, including Jon’s role as a comedian, Obama inviting rapper Common to the White House, and the threat of terrorism. With a couple of exceptions of dramatic embellishment, the two kept their conversations restrained and respectful. Stewart’s appearances showed he was more than able to hold his own against O’Reilly, even out of his element, and made smart, relevant points in the process.

#6: Mark Twain Prize Acceptance Speech (2022)

The Kennedy Center Mark Twain Prize for American Humor

It’s only fitting that Stewart was awarded a prize named for one of the most renowned satirists ever known. The Mark Twain Prize for American Humor is an honor bestowed upon comedians who have made an undeniable impact on society. And many, including members of Stewart's "Daily Show' staff, paid touching - and humorous - tribute to their former boss. When it was his turn to speak, Stewart was honored and humbled. Speaking from the heart about his journey and the people who’ve inspired him, Stewart shows his wonderfully relatable side. Best of all, he leaves us feeling inspired about the hope of a better world.

#5: Interview With Malala Yousafzai

“The Daily Show” (1996-)

For a guy who meets with everyone, from movie stars to world leaders, you wouldn’t expect Jon Stewart to be humbled by much. However, he was reduced to childlike wonder and amazement when he met with Pakistani activist and Nobel Prize laureate Malala Yousafzai. As Malala relayed her inspirational story to Jon, he couldn’t help but listen with his hands up to his face, reduced to speechlessness at the amazing things she said. Malala remained a source of inspiration for Jon and “The Daily Show,” as her one-of-a-kind activism brought light after some of the darkest times in recent history.

#4: “Daily Show” Farewell (2015)

“The Daily Show” (1996-)

When Jon Stewart first announced he would be leaving “The Daily Show,” it didn’t feel real. After more than 16 years behind the desk, Stewart had gone from “late-night host” to cultural icon. His final episode was everything you’d hope for, with past correspondents and plenty of other exciting cameos. But as it often goes with Stewart, the best part was just hearing him speaking with self-deprecating sincerity. In the closing moments of the show, he talked about his immense gratitude for the job and those who helped make it possible. Now, that’s how you do a proper goodbye.

#3: Crushing “Crossfire” (2004)

“Crossfire” (1982-2005; 2013-14)

The political debate show “Crossfire” had been a staple of CNN’s lineup since 1982. Then Jon Stewart came to visit. While hosts Paul Begala and Tucker Carlson thought Stewart was coming on to promote “America (The Book),” he was really there to ask them to “stop hurting America.” He spent the whole segment taking the show and the hosts to task, calling it partisan hackery and saying that instead of nuanced debate, they just showcased both extremes of the political spectrum. The confrontation even resulted in Stewart referring to Carlson by a rather unflattering term. The segment immediately went viral and CNN cancelled the program in 2005, with the network noting that they agreed with Stewart’s criticisms.

#2: September 11th Response (2001)

“The Daily Show” (1996-)

9/11 affected nearly all TV shows produced in New York and “The Daily Show” was no exception. The show returned on September 20th, 2001 for the first time since the attacks, opening with a monologue from Stewart. After offering condolences to the victims, he began to break down. To Jon, this was not a time for despair, because he saw the purpose of America realized. He closed the emotional monologue with a message of hope, saying what the view from his home now is. Stewart’s response to the tragedy set the tone of the show for years to come, and served as a reminder of how powerful he can be, even when he’s not telling jokes.

#1: Advocating for First Responders

One of the causes that seems closest to Jon Stewart’s heart is healthcare coverage for 9/11 First Responders. Because of their work at Ground Zero after the September 11th attacks, these members of the NYPD and Fire Department of New York face health risks, including respiratory illnesses and cancer. On “The Daily Show,” Stewart campaigned tirelessly for the Zadroga Act – a bill that would provide financial aid to those affected – while also criticizing Congress for dragging their heels and other media members for not covering the subject more. Ultimately, the bill was passed in 2011; however, Stewart was back in front of lawmakers in 2019 to oppose cuts to the 9/11 Victim Fund and to ensure compensation past the 2020 expiry date. Stewart choked up as he chastised the half-empty room, earning himself a standing ovation.

Did we forget another entertaining clip from Stewart’s career? Let us know in the comments below.