10 of Jon Stewart’s Best Moments on ‘The Daily Show’

Since taking over the host chair in 1999, Jon Stewart has transformed The Daily Show into one of the most important and sociopolitically relevant news sources on television – and a damn funny one at that. Sadly, Stewart’s incredible 16-year reign is about to come to an end. After announcing his departure from the show earlier this year, Stewart officially hosted his last episode on August 6th.

While trying to narrow down Stewart’s best segments from his time on air is close to impossible, we decided to give it our best shot ahead of his final episode. Here are ten of the most unforgettable moments from Stewart’s time on The Daily Show:

1. Crossfire takedown

While this wasn’t a Daily Show segment, his appearance on CNN’s Crossfire was undoubtedly one of Stewart’s most extraordinary moments – perhaps even the most extraordinary. Stewart was invited on the show a month before the 2004 election. He had only been hosting The Daily Show for five years at that point, but that didn’t make him any less skill at delivering a powerful critique. While co-hosts Paul Begala and Tucker Carlson obviously expected a friendly chat, Stewart proceeded to eviscerate them, pointing out how their show trivialized healthy public discourse and hurt America in the process. Carlson tried to turn the tables, but it was clear who came out on top in the end. When a new CEO took over CNN in 2005, he canceled Crossfire and openly admitted that Stewart’s criticisms were part of the reason the program was axed.

2. Jim Cramer interview

Few of Stewart’s takedowns have been as spectacular and cringe-inducing as his 2009 interview with Cramer. Stewart unleashed the full extent of his scorn on the Mad Money host, using clips of Cramer’s own past assertions to make it clear that he and CNBC as a whole misled the public in lead-up to the 2008 financial crisis. “When I watch that, I can’t tell you how angry that makes me because what it says to me is you all know,” Stewart asserted as Cramer squirmed in his seat. “So now to pretend this was a crazy once-in-a-lifetime tsunami that nobody could have seen coming is disingenuous at best, and criminal at worst.”

3. Indecision 2000

Stewart helped The Daily Show conquer political satire and one of his earlier, most triumphant moments came during the race between presidential candidates George W. Bush and Al Gore. Stewart had a field day with the drawn-out recount of votes in Florida and the episodes covering the recalculation earned The Daily Show its first Emmy. The “Indecision” format became one of the show’s signature features and helped solidify the series as one of the most politically relevant programs on television. Needless to say, we’ll miss Stewart terribly this next election.

4. 9/11 monologue

Stewart has a way of covering heartbreaking tragedies that’s both honest and meaningful. Never has that been clearer than in his opening monologue, following his return to air after 9/11. Discussing the tragedy, a visibly emotional Stewart spoke eloquently and candidly. “I’m sorry to do this to you,” he said. “It’s another entertainment show beginning with an overwrought speech of a shaken host, and television is nothing if not redundant.”

5. Glenn Beck spoof

Stewart held absolutely nothing back when he took it upon himself to poke fun at Beck’s dramatic hosting style. In the 2011 episode, Stewart spent a full 15 minutes ruthlessly parodying Beck’s exaggerated theatrics – down to the glasses and chalkboard. “Finally, a guy who says what people who aren’t thinking are thinking,” Stewart quipped in the bit. The entire thing still is one of the best examples of the biting satire that Stewart is known for.

6. War on Christmas

Another favorite of Stewart’s many takedowns of Fox News is his hilarious tirade against the so-called War on Christmas. Stewart had it out with the channel’s ridiculous coverage of the holiday, especially Bill O’Reilly. In this particular clip, Stewart basically summed up Fox’s entire argument with four words: “Who gives a sh-t?”

7. Bush vs. Bush

One of The Daily Show‘s best uses of clip montages came in this segment, when tSewart essentially moderated a debate between George W. Bush when he was a Texas Governor and George W. Bush as a presidential candidate. The result? Let’s just say Bush and Bush were definitely not in agreement, with his responses to similar issues changing drastically in a relatively short period. While the entire Bush administration proved to be gold for Stewart, this 2003 piece remains remains a stand-out.

8. Gitmo

Every now and then, Stewart brought out an Elmo puppet with a beard named Gitmo to discuss his life as a detainee Guantanamo Bay detention camp. He used the puppet to highlight everything from the precarious balance between safety and free society to the conditions prisoners in the facility face. It’s a heavy topic, but a hilariously absurd way of covering it – especially since the cameras often caught Stewart voicing Gitmo.

9. Chaos on Bulls–t Mountain

Fox News is never safe from Stewart’s wrath, but Mitt Romney’s infamous “47 percent” video during the 2012 presidential campaign ignited a new level of contempt for the channel’s anchors. Stewart rips apart Fox’s coverage of the video, dissecting the anchors’ defense of it comment by comment. It was one of Stewart’s most brilliant and insightful analyses to date..

10. Wit Happens

Many members of the media were left surprised when Stewart criticized Obamacare, despite that the host has never been shy about airing his grievances towards either party. Still, when countless anchors made a point of expressing their shock that “even Jon Stewart” expressed disapproval towards Obama’s plan, he decided to mock them – by bringing on a full gospel choir singing “Go f— yourself,” of course. Seriously, how much will you miss this guy?

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