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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 1

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

Via peabodyawards.com

14 On Brian Williams

13 The Oscars

Via oscars.org

12 Calling Out FOX on Ferguson, Missouri Coverage

11 Mike Huckabee and Gay Marriage

Via rollingstone.com

10 Ricky Gervais Interviews

9 Jim Cramer Interview

Via jpjam.wordpress.com

8 Nancy Pelosi and Corruption

Via thedailyshow.cc.com

7 Eric Garner Grand Jury Decision

6 Glenn Beck Parody

5 The 9/11 Health and Compensation Act Show

Via thedailyshow.cc.com

4 The War on Christmas

Via thedailyshow.cc.com

3 Any Bill O’Reilly Interview

2 9/11 Monologue

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.

Sources: time.com, boston.com, mashable.com, deadline.com, cnn.com, ibtimes.com, harikari.com, cbsnews.com, huffingtonpost.com

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The 15 Best Jon Stewart Moments