24 Iconic Moments From the Daily Show’s ‘Jon Stewart’ Era

Jon Stewart’s brand of unflinching comic satire made The Daily Show one of the network’s most popular series. His evening slot alongside The Colbert Report was a daily favorite among many politically aware viewers who enjoyed their news with a side of irreverent satire. Stewart has given us plenty of memories over his tenure — has it really been nine years?

1. Indecision 2000: The Florida Recount (2000)

Early on Stewart’s Daily Show tenure, he covered George W. Bush as his comic material. First, Bush had to win the election, which centered on the recount between Bush and Al Gore, ending in a controversial win for the Texan. When the count was over, Stewart broke the news to his nonplussed audience, softening the blow when he said, “And the crowd loves it!”

2. The Post-911 Show (2001)

Only two years into Stewart’s reign on Comedy Central’s dinnertime spot, he covered a tumultuous geopolitical moment when the World Trade Center towers fell. “It’s another entertainment show beginning with an overwrought speech by a shaken host,” began Stewart that fateful day. His poignant monologue captured a black day for all Americans, especially New Yorkers who felt the pain of an attack on their town.

3. His John Oliver Collaborations

John Oliver’s funniest moments were on the street, speaking to the unsuspecting public, but occasionally, he would drop into the Daily Show studio. In a 2008 segment named “Britain’s Fallen Soldiers,” Oliver reports on President Bush’s attempts to draft NATO member states’ soldiers into Southern Afghanistan.

However, each “top brass” title in his segment has an outrageous name. Oliver had changed the names without telling Jon Stewart, who is struggling to keep it together as “Vice Marshall Jock Stirrup” speaks to a CNN reporter. If that wasn’t enough, he renders Stewart inoperable with a list of fallen British World War Two soldiers with hilarious-though-unrepeatable names. 

4. “Cheney’s Got a Gun” (2006)

The Bush administration provided what seemed like ready-made comic material for The Daily Show over eight years. One such humorous nugget was when Vice President Cheney shot a friend in the face while hunting. “Thank you, Jesus,” quips Stewart before unloading a few rounds on Cheney, who incidentally became the first veep to shoot a man “since Alexander Hamilton.”

5. Jon Stewart vs. Jim Cramer (2009)

The MSNBC Mad Money host Jim Cramer is renowned for his abrasive, over-the-top, confrontational presentation of financial markets analysis. Referring to what he considered an audience grift on the network’s part, Stewart tore strips off him in a 2009 interview. “It’s a game that you know…is going on,” blasts Stewart to an uncharacteristically quiet Cramer, “but that [sic] you go on television as a financial network and pretend isn’t happening.” 

6. The 9/11 First Responders Senate Filibuster (2010)

Jon Stewart has long been a champion for America’s emergency services. When US Senate Republicans, led by Senate minority leader Mitch McConnell, filibustered the 9/11 Health and Compensation Reauthorization Act, which would help the 9/11 first responders suffering the after-effects of being in the World Trade Center’s toxic rubble. Stewart gave several of these American heroes suffering considerable illnesses a platform to discuss their plight. 

7. The “Rally To Restore Sanity And/or Fear” (2010)

During President Obama’s first term, Jon Stewart teamed up with his contemporary, Stephen Colbert, to bring a rare Daily Show outdoor event to Capitol Hill: “The Rally for Sanity and/or Fear” event. The comic friends aimed to show that America wasn’t divided like the news media tried to portray (and still do). The concert featured a performance from The Roots, Stephen Colbert dressed as Evel Knievel, and an award ceremony for Velma Hart, a Washington D.C. non-profit worker and Obama supporter who lost her job after criticizing the former president in a town hall meeting. Stewart presented Hart with a “medal of reasonable-ness” for staying true to her beliefs. 

8. The Iran Coverage (2010)

Stewart made his feature film directorial debut in 2014 with the movie Rosewater, chronicling the story of journalist Maziar Bahari’s arrest by Iranian authorities following a 2010 Daily Show interview on Iranian state persecution. While some might say it was Stewart’s fault, he gave a face to the Iranians’ oppression while shining a light on their struggles for the world to see. 

9. The Bill O’Reilly Relationship

Stewart has few enemies during his Daily Show stretch, though one many fans anticipated was Fox News’ Bill O’Reilly. In one exchange, Stewart responds to Bill O’Reilly’s observation that the New Yorker was “going to Hell.” As we know, Stewart loved sparring with his Fox News arch-nemesis. “You’re Hell doesn’t scare me; I make a living watching Fox News eight hours a day,” he says. “I’m already in Hell.” 

10. The Mayor Bloomberg Drinks Ban (2012)

In a  “Drink Different” segment, Stewart destroys New York City Mayor Michael Bloomberg’s proposed 16 oz cap on sugary drinks. Characteristically, Stewart enjoys the segment news B-roll footage with a “Big Gulp” in his hands, taking gleeful sips between clips before ridiculing Bloomberg’s civic overreach. Funnier still, when Bloomberg appeared in a later interview, Stewart made a point of having a giant drinking cup during the interview. 

11. “Democalypse 2012” (2012)

Stewart loved election cycles, and unlike many other pundits, he tried to keep things balanced and his liberal beliefs aside. During the 2012 Obama vs. Romney election season, Stewart was in his element, roasting both Romney and Obama. His response to Romney’s “Binders full of women” gaffe was typically cheeky. “Binder of women; book of broads…whatever!” joked the comic. 

12. The Bassem Youssef Interview (2013)

In 2013, Stewart interviewed Bassem Youssef, an Egyptian TV presenter much like Stewart, who hosted the Egyptian satirical comedy show Al Bernameg. The Egyptian secret police had just arrested Youssef for daring to satirize Muslim Brotherhood leader and newly elected president Mohamed Morsi. The Daily Show host discovered a kindred soul in Youssef’s irreverent, sarcastic comedy style. 

13. The Roast of Rob Ford (2013)

“I want to ask you a question at home: do you have children?” asks an earnest Jon Stewart before revealing a bait-and-switch. “Because if you do, you might want to go and wake them up and bring them downstairs…this is more important than school.” He then launches into a hilarious roast of former Toronto mayor Rob Ford’s response to reporters on improper conduct allegations from a staffer, with the mayor deflecting rumors, saying he “had enough to eat at home.” 

14. Interviewing Malala Yousafzai (2013)

I Am Malala became a global sensation in 2013, and author Malala Yousafzai joined the Daily Show‘s interview desk upon the release of her book. Stewart’s easy manner and generous interviewing style allowed Malala to expose the terrorists’ evil acts — not least against women — to the world.

15. The Deep-Dish Pizza Episode (2014)

Throughout his career, Stewart has defended his hometown on several fronts, including his New York pizza vs. Chicago deep-dish pizza speech. “Deep-dish pizza is not only not better than New York pizza,” says the New Yorker. “It’s not pizza.” What follows is a rant on the construction of deep-dish pizza that only Jon Stewart can do. “This is tomato soup in a bread bowl,” screams an impassioned Stewart in a rant that riled Chicago natives everywhere. 

16. The Israel Question (2014)

The Middle has always been a hotbed of contention, and the topic’s polarizing effect reverberates today stronger than ever. In 2014, Stewart presented a well-crafted segment attempting to address the nuance in the Israel-Palestine situation. To mimic the abuse speakers on either side of the debate receive, his Daily Show subordinates rise from behind the desk to hurl abuse each time he attempts to discuss any point. The clip is The Daily Show at the peak of its powers. 

17. The Barack Obama Interview (2015)

Former president Barack Obama made many TV appearances, though few resembled a proper interview. However, when he joined Stewart for a midweek interview in front of a studio audience, he faced stern questioning on the poor Veterans Association performance, among other points. The fact that Obama agreed to an interview was a testament to the trust people used to have in a Daily Show appearance. 

18. The CNN Takedowns

When the mysterious case of missing Malaysia Airlines flight MH370 was top of news reports worldwide, Stewart couldn’t resist throwing shade at the news channel’s 24-7 blanket coverage of “everything in their bag of tricks.” He ridicules CNN’s giant floor maps, big fake airplanes, little fake airplanes, and airplane holograms. “You’re telling them what a plane looks like?” jokes Stewart when Wolf Blitzer reveals the vessel’s dimensions. 

19. The Charleston Church Shooting Response (2015)

Amid the irreverent comedy set pieces that made the show so good, Stewart would pause to reflect on America’s bigger problems, including mass shootings. “What blows my mind is the disparity of response between when we think people that are foreign are going to kill us,” says a solemn Stewart,” and us killing ourselves.” He was speaking in the wake of the awful massacre at the Emanuel African Methodist Episcopal Church in Charleston, South Carolina, where 10 African Americans lost their lives. 

20. The “Deflategate” Scandal (2015)

In 2015, it emerged that elite-level quarterback Tom Brady knew about footballs being deflated before an important play-off match, better known in the media as “Deflategate.” Of course, New York Giants fan Jon Stewart couldn’t resist roasting the now-retired seven-time Super Bowl winner. “Did Michael Jordan cheat to get his six championships?” he asks in a monologue. “No: in fact, Michael Jordan decided to play a sport he sucked at just to give other people a chance.” 

21. “Majority Retort” (2015) 

Stewart always enjoyed large political events, and none gave him more gag fodder than the post-State of the Union Address speeches from Capitol Hill. Citing past contenders such as “Dry Lips McGee” (in reference to Marco Rubio‘s famous “glass of water” incident), he reveals the “Impody” award nominees for 2015. “Here’s a tip: if you’re looking to run for president,” he says to award-winner Ted Cruz, “maybe you shouldn’t make your response to the State of the Union look like a ransom video.”

22. The Charlie Hebdo Address (2015)

2015 began with shocking news footage from Paris when Islamic terrorists stormed the offices of the satirical magazine Charlie Hebdo, murdering twelve journalists, cartoonists, and contract workers. “I think we’ll all agree that 2014 was not a great year,” begins his monologue, “for people.” The gravity of the attack on free speech reverberated through the secular journalism world, and Stewart treated the news with 

23. “Democalypse 2016” (2016)

“He owns a V.H.S. copy of Tootsie!” says Stewart in his mock newsroom impersonation voice. ​​”He wears socks on his hands and gloves on his feet!” His jokes follow a montage of talking heads slamming Bernie Sanders before his presidential candidacy announcement. Bernie Sanders had an ally in Stewart, who defended the Vermonters’ stance on banking, social security, and campaign finance reform in a fine episode during the 2016 presidential election run-in. 

24. The Fox News Takedowns

When Stewart announced his (first) retirement from Daily Show life, CNN’s Brian Stelter aired a montage of Stewart destroying his “favorite” network, Fox News. Some of his takedowns have been legendary. “We read the chain emails your grandma gets in her inbox out loud like they were true,” says the host in trademark fashion during one take.