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The 15 Best Jon Stewart Moments

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The 15 Best Jon Stewart Moments


In February, comedian, political satirist and television host Jon Stewart announced he was retiring from the popular Comedy Central show The Daily Show. Stewart had taken over at the show in January 1999, replacing the outgoing Craig Kilborn and transforming the show from being focussed on pop culture to one about politics and the media. Over the following 16 years, Stewart added his brand of humor and satire to the daily assessment of the biggest headlines. More often than not, the 52-year-old found himself poking fun at the political leadership in Washington – usually the more conservative leaders but no one was really safe. When not getting a laugh at the politicians’ expense, Stewart often took on the news networks, like MSNBC, FOX and CNN, highlighting the multitude of ridiculous and sometimes bizarre programs and statements that make their way onto the airwaves.

In November 2010, TIME had a poll asking who the most trusted newscaster was in the United States. A total of 44% of those who answered said Jon Stewart. While that may be a troubling commentary on the state of American news, Stewart often repeated that The Daily Show was a comedy show first and foremost. Nonetheless, over the years the show and especially its host have grown in popularity with over two million viewers tuning in every night to watch. He’s enjoyed some funny interviews with celebrities and politicians – and some not so funny and rather awkward ones as well. He’s been involved in ‘feuds’ with other television personalities and made more than one of them appear foolish. On top of all of this Stewart has even hosted the Oscars and led a rally in Washington DC.

The following looks at 15 of the most memorable Jon Stewart moments. The majority of them, unsurprisingly, come from his time on The Daily Show. Most, but not all, involve moments when he went after the Republican Party, its various members or the right-leaning media. Indeed, whether satirizing an actual event or political development or just being plain immature at times, Jon Stewart provided some memorable moments and some pretty big shoes for the next Daily Show host to fill.

15. Indecision 2000



Indecision 2000 was a series of specials which spoofed the US presidential elections. It set the precedent for much of the show’s future in that correspondents went out ‘into the field’ to interview political figures and provide Stewart with more political-comedy fodder. Stewart provided a symbol for those who felt disenfranchised by the lengthy vote recount and controversial Supreme Court ruling. Indicating what direction Stewart and the show were heading, President Bush was quoted as saying that he wasn’t elected to serve one party. To which Stewart replied “you were not elected.”

14. On Brian Williams

It isn’t always the politicians that come under fire from Jon Stewart. Just a day before he announced his impending retirement, the comedian took on the issue of Brian Williams and the news anchor’s ‘exaggerations’ of what happened during the Invasion of Iraq. Stewart attributed Williams’ scandal and subsequent suspension to what he called Infotainment Confusion Syndrome – a condition which he attributed to the newsman’s duel role as celebrity and journalist. The main barb in Stewart’s story was not aimed at Williams but the journalists criticizing him. In classic Jon Stewart fashion, the comedian joked that at least the media was finally criticizing someone for misleading them during the Iraq War.

13. The Oscars



Perhaps surprisingly, Jon Stewart was picked as the host for the 78th and 80th Academy Awards in 2006 and 2008. Traditionally, the hosts have been ‘safe’ acts that worked in Hollywood for their careers and knew the politics and people. Stewart had relatively little experience in Hollywood at this point and many wondered how his sense of humor would mesh with the show. Naturally, those expecting some sort of earth shattering Daily Show-style bonanza were let down. Those expecting Jon Stewart to be Jon Stewart were not. Overall, reviews were mixed over the course of both shows but some of the bigger names in the game, like Roger Ebert, wrote that Stewart worked well and made up for an awards show which lacked any surprises or excitement.

12. Calling Out FOX on Ferguson, Missouri Coverage

In FOX News, Stewart found an unending source of fodder for his opening monologues. The August 9th 2014 shooting of African-American Michael Brown in Ferguson, Missouri by a white police officer captured the attention of the nation and its news outlets for much of the second half of 2014. The protests, looting and violence which followed a grand jury decision not to indict the police officer had everyone analyzing and commenting on the state of law and race relations in the United States. FOX News’ coverage played heavily on the notion that the ‘race card’ was being played unfairly and that the whole situation in Ferguson was not about white vs black in the United States. Blending FOX News clips with his traditional sense of humor, Stewart dedicated half of his show to this issue, in the process producing a rather profound statement on race relations in the country.

11. Mike Huckabee and Gay Marriage



It seems like every few years since 2009, conservative Mike Huckabee and Jon Stewart got involved in an argument over gay marriage, yet the former Arkansas Governor keeps coming back for more. First, Huckabee stated that people should live the way they want except in marriage which is for men and women only. Then, in 2012, the two went at it again over Huckabee’s definition of marriage. A third attempt in 2015 had the ex-governor equating gay marriage to asking a Jew to serve bacon-wrapped shrimp. Naturally, it all provided more than enough fodder for Stewart use creating some funny and memorable interview moments.

10. Ricky Gervais Interviews

Every now and then, Jon Stewart had a guest appearance by someone who really clicked, producing a memorable interview. This was generally the case with Ricky Gervais. Any time the British comedian came onto the set the audience was usually left in stitches and any planned questions were thrown right out the window. In the short span of a few minutes, the discussion could go from Gervais’ new television show to a discussion about dying from getting hit by a truck while mooning traffic. In a 2012 interview, Stewart brought out the best (or worst) in Gervais and the discussion ultimately ended with the two comedians discussing pandas on Viagra and having sex with raccoons.

9. Jim Cramer Interview



If you’ve ever seen CNBC’s Mad Money then you’ve seen Jim Cramer. You know, he’s the guy wearing the shirt and tie, jumping around and yelling market advice as if he’s just snorted a line of cocaine. In March 2009, in the midst of the financial crisis, Jon Stewart had Jim Cramer come on The Daily Show. Stewart criticized Cramer and CNBC and basically shamed them all for playing a role in the financial mess. After Cramer had stated that he never undertook any dodgy decisions and strategies in the market, Stewart unleashed a clip which suggested otherwise. For the rest of the interview, every attempt Cramer made to get ahead of Stewart in the roasting was foiled. In this case, instead of leaving the audience laughing, viewers were left wondering what sort of clown college was looking after their money.

8. Nancy Pelosi and Corruption



For those who might say Jon Stewart was only after Republicans and Conservatives, they clearly haven’t seen the Nancy Pelosi interview. The January 2014 interview with the House minority leader asked some hard questions which many thought wouldn’t be asked of a ‘fellow’ liberal. If the former speaker had any ideas about trying to pin all the problems in the government on the Republicans, Stewart clearly didn’t think she was all innocent either. Throughout, Pelosi was left looking visibly uncomfortable as Stewart hammered home questions about special interest money and corruption in the government. It wasn’t a liberal love-in as some might have expected and the whole thing made Pelosi look rather incompetent.

7. Eric Garner Grand Jury Decision

In July 2014, Eric Garner was confronted by NYPD officers who suspected him of selling loose cigarettes. The incident ended with Garner in a chokehold on the ground where he eventually died from compression of the neck and chest. A grand jury opted not to indict the police involved in the death which resulted in further protests because an unarmed African-American had been killed by white police officers. Stewart’s assessment highlighted that, unlike the shooting in Ferguson Missouri, video footage left no ambiguity about the death of Eric Garner. The comedian also called out Rudy Giuliani, Sean Hannity and Rand Paul for attempting to deflect the real reason of the death away from the extreme actions of the officers.

6. Glenn Beck Parody

Anyone who has watched Stewart over the years knows that there have been a few key political and media personalities who he loves to go after. For a few years, at least, FOX contributor Glenn Beck was a Jon Stewart favorite. It wasn’t just that Beck worked for FOX but that he had some rather extreme or sometimes bizarre views and opinions of America, its people and political system – usually involving Nazis or Marxists taking over the government. Enter Jon Stewart. In 2010, the comedian launched into an all-out impression of Beck, complete with chalk board and conspiracy theories. Stewart’s several minute long rant followed the Glenn Beck formula and showed how Jesus could transform into the Ayatollah and that Sesame Street’s Bert (of Bert and Ernie fame) was actually Adolf Hitler. Interestingly enough, Beck left FOX just a year later with some saying it was because his views were damaging the image of FOX News.

5. The 9/11 Health and Compensation Act Show



In the years following the 9/11 attacks, news outlets gave limited air time to the debate concerning the funding for the care and medical services of first-responders who were sick and dying as a result of material they were exposed to at ground zero. Known as the James Zadroga 9/11 Health and Compensation Act, if passed the legislation was meant to give first responders who were sick the funding to pursue medical care. In early December 2010, the Senate was unable to pass the act because of a Republican filibuster. Just days later, Jon Stewart dedicated a show to the Act, one which was especially damning of the Republicans who blocked it. In addition to the opening monologue which shamed the government, Stewart interviewed four 9/11 first responders who were sick or dying and followed that up with an interview with Republican Mike Huckabee. Coincidentally, in the two weeks following the show, the act was passed and signed into legislation with some citing Stewart as a motivating force.

4. The War on Christmas



Come December, you can bet that Jon Stewart and the people at FOX News open up their now annual debate concerning whether there is a movement against Christmas and the way it is displayed and/or advertised in the United States. Those at FOX, like Bill O’Reilly, argue that Christmas is being assaulted from all directions and the proof is that, among many things, one must now say ‘Happy Holidays’ instead of ‘Merry Christmas.’ Stewart’s response is to create a collage of FOX clips in which various personalities have their say, often exaggerated or full of hyperbole. Then adding in his own witty analysis he makes everyone look more than a little foolish. The back and forth can be very funny, especially when it involves FOX’s Megyn Kelly arguing that it’s a historic fact that Santa Claus and Jesus Christ are the same race.

3. Any Bill O’Reilly Interview

If there’s anything Jon Stewart has shown us over the years it is that you shouldn’t try and have a serious argument with a comedian – especially one who seems to know something about what they are saying. Nonetheless, over the years FOX personality Bill O’Reilly has often entered into back-and-forth debate and face-to-face interviews with Jon Stewart usually in an attempt to get the comedian to admit something. On more than one occasion, Stewart has left O’Reilly backtracking or looking caught out after an exchange. A perfect example was when O’Reilly tried to get Stewart to admit that President Obama’s invitation of Common to the White House was inappropriate because the rapper had supported convicted murders. The FOX host was left trying to dance his way out of his own trap when Stewart asked if that applied to the other presidents who had invited Bono or Bob Dylan to the White House – both of whom had songs supportive of people who had been convicted for murder.

2. 9/11 Monologue

The attacks of September 11th 2001 devastated parts of the United States and shook the nation collectively. In the hours and days that followed, every pundit, journalist and news anchor appeared at one time or another and attempted to convey their feelings on the matter as everyone tried to digest what had happened. Following David Letterman’s return to tv on September 17th, Jon Stewart began his September 20th show with an emotional opening where he had to stop to compose himself on more than one occasion. It was an honest and unscripted speech by an American and New Yorker attempting to make sense of a horrible day.

1. Crossfire

Crossfire was a CNN show which started airing in 1982 and was meant to address the political issues of the day with two hosts who each addressed the political right and left. In 2004, the show was hosted by Tucker Carlson and Paul Begala. Everything seemed fine until Jon Stewart came on the show as a guest in October 2004. The comedian went after the show for failing to address real issues and watering down everything into talking points with only a left or right political meaning. Anyone who has watched the show could only feel uncomfortable for the hosts as Stewart ultimately called the whole production a failure. Attempts to counter the criticism with their own only made things worse as Stewart responded by stating that he, unlike the hosts of Crossfire, didn’t have an obligation to report and deal with real and important issues because he was ultimately a comedian on a comedy show. Within three months, Crossfire was cancelled.

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