The 15 Best Jon Stewart Moments

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.”
15. Indecision 2000

14. On Brian Williams

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.
14. On Brian Williams

13. The Oscars

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.
13. The Oscars

12. Calling Out FOX on Ferguson, Missouri Coverage

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.
12. Calling Out FOX on Ferguson, Missouri Coverage

11. Mike Huckabee and Gay Marriage

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.
11. Mike Huckabee and Gay Marriage

10. Ricky Gervais Interviews

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.
10. Ricky Gervais Interviews

9. Jim Cramer Interview

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.
9. Jim Cramer Interview