With a reputation for being a funnyman even in school, Jon Stewart moved to New York City in 1986 to try his hand at the comedy club circuit. In 1989, he began hosting Comedy Central's Short Attention Span Theater, and in 1993, due in large part to the support of his friend David Letterman, Stewart started hosting The Jon Stewart Show on MTV, the first talk show on that network. Also in 1993, he was a finalist to replace David Letterman on Late Night, but the position ultimately went to Conan O'Brien. In 1994, Paramount pulled the plug on The Arsenio Hall Show and, with MTV, launched an hour-long syndicated late-night version of The Jon Stewart Show. The show, broadcast in 2:00 or 3:00 AM timeslots by some local stations, was a ratings flop, and it was cancelled in June 1995. Stewart had also previously hosted the unsuccessful You Wrote It, You Watch It on MTV, which invited viewers to send in their stories to be acted out.
In 1999, Jon Stewart began hosting The Daily Show on Comedy Central when
Craig Kilborn left the show. Since that time, he has hosted all airings
of the program, save for a scant handful where correspondents such as
Stephen Colbert have filled in at the anchor desk. In 2005, The Daily
Show and Jon Stewart received two Emmy Awards and a Best Comedy Album
Grammy Award for the audio book edition of America (The Book).
Jon Stewart also hosted the Grammies twice, in 2001 and 2002. In the middle of the 2001 broadcast, after laying a number of comedic duds, Stewart did what he encourages most public officials to do, and owned up to his bad hosting: he said, "Ladies and gentlemen, I just want to say I feel your scorn and accept it". When Stewart returned to host the next year, his comedy was more successful. Joking about the performance of the song "Lady Marmalade," he said, "Our next performance is from the movie Moulin Rouge!, a film about a time when the whorehouses were about the music!" When the O Brother, Where Art Thou? soundtrack won Album of the Year and an immense number of people walked up on stage, Stewart quipped, "I don't know what you may have heard, but you were only supposed to go on stage if you worked on the O Brother, Where Art Thou? soundtrack, not if you heard it."
In the middle of 2002, amid rumors that David Letterman was going to make a jump from CBS to ABC when his contract ran out with CBS, Stewart was rumored to be the person who would take over Letterman's show on CBS. Ultimately, Letterman renewed his contract with CBS, and ABC gave another Comedy Central figure, Jimmy Kimmel, his own show following Nightline. In a 2002 episode of Saturday Night Live that Stewart was hosting, a "Weekend Update" sketch poked fun at the situation. In the middle of the sketch, "Weekend Update" host Jimmy Fallon said that he couldn't continue doing the broadcast, and he brought Stewart in to replace him. Stewart glowed with excitement and chattered to himself about his chance to prove himself on network television. His pep talk went on too long, however, and before Stewart could deliver any headlines, Fallon returned and said he would be able to finish out the broadcast himself.
Still, many people believe that when Letterman does retire, Stewart (a fellow Viacom employee) will replace him to continue the Late Show franchise and compete with Conan O'Brien. At a London appearance on December 11, 2005, when asked if he would replace Letterman, Stewart said it would be unlikely, because on Comedy Central he has creative independence that CBS would probably not give him. In reference to Letterman's wealth, he stated, "Really, who needs all that money?"
Although best known for his work on The Daily Show, Stewart has also had roles in several television series and movies. He often makes fun of his film appearances, as they have largely been in movies considered to be flops. He usually singles out the high-profile bomb Death to Smoochy, in which he played a treacherous television executive. He also appeared in the cult favorite Half Baked, and he played a romantic lead in the film Playing by Heart. Other movie appearances include Big Daddy as Adam Sandler's best friend and The Faculty, and small part as a news correspondent in Jay and Silent Bob Strike Back. He has guest-starred on such television shows as The Nanny, Spin City, and NewsRadio, in addition to the Saturday Night Live episode he hosted in March 2002.
Jon Stewart attracted much attention as a result of an unusual, awkward, and heated television exchange with CNN's Tucker Carlson on Crossfire in October 2004. Stewart decried the state of television journalism and pleaded with the show's hosts to "stop hurting America", and referred to both Carlson and co-host Paul Begala as "partisan hacks". He also asserted that Crossfire had failed in its responsibility to inform and educate viewers about politics as a serious topic. When Carlson told Stewart he wasn't as funny in person as he was on his show, Stewart retorted, "You're as big a dick on your show as you are on any show" (transcript). This exchange became one of the most widely viewed Internet videos to date (both publicly on iFilm and from other sources) and a topic of much media discussion. In January 2005, CNN announced that it was cancelling Crossfire. When asked about the cancellations, CNN's incoming CEO, Jonathan Klein, stated that although he made the decision six months before Stewart's appearance on the show, he "wholeheartedly agrees" with Stewart's "overall premise."
Jon Stewart has received the prestigious Peabody Award twice for the coverage of the 2000 and 2004 U.S. presidential elections on The Daily Show. He was also named one of the 2005 Time 100, an annual list of 100 of the most influential people of the year by Time Magazine. In the magazine article, Tom Brokaw described Stewart as one of the few people who represent true Athenian democratic values.
The Daily Show recently premiered on UK television at the end of 2005 on new digital channel More4. The mix of satire and comedy has had a good response from the British public and a growing fanbase across the Atlantic is now starting to build up.
On January 5, 2006, Jon Stewart was officially announced as the host of the 78th Academy Awards (Oscars), which will be held at the Kodak Theatre in Hollywood on March 5, 2006.
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