1998–2015: The Daily Show
In 1998, Stewart hosted the television special Elmopalooza, celebrating 30 years of Sesame Street. He has guest-starred on other sitcoms, including The Nanny, Dr. Katz, Professional Therapist, Spin City and NewsRadio. The same year, Stewart released his first book, Naked Pictures of Famous People (1998), a collection of humorous short stories and essays. The book reached The New York Times Best Seller List. In the mid-1990s, Stewart launched his own production company, Busboy Productions, naming the company in reference to his previous job as a busboy. Stewart signed a deal with Miramax to develop projects through his company, but none of his ideas have been produced. After Stewart's success as host and producer of The Daily Show, he revived Busboy Productions with Daily Show producers Ben Karlin and Rich Korson. In 2002, Busboy planned to produce a sitcom for NBC starring Stephen Colbert, but the show did not come to fruition.
In 1999, when Craig Kilborn left the show to replace Tom Snyder on The Late Late Show, Stewart began hosting The Daily Show on Comedy Central. The Daily Show blends humor with the day's top news stories, usually in politics, while simultaneously poking fun at politicians, newsmakers, and the news media. In an interview on The O'Reilly Factor, Stewart denied the show has any intentional political agenda, saying the goal was "schnicks and giggles" and that "[t]he same weakness that drove me into comedy also informs my show", meaning that he was uncomfortable talking without hearing the audience laugh. In his first Daily Show on-air appearance on January 11, 1999, Stewart told his guest that evening, Michael J. Fox, that he felt as if "this is my bar mitzvah". His style was described by one critic as, "Stewart does not offer us cynicism for its own sake, but as a playful way to offer the kinds of insights that are not permitted in more serious news formats that slavishly cling to official account of events."
He appeared in Half Baked as an "enhancement smoker" and in Big Daddy as Adam Sandler's roommate; he has joked on the Daily Show and in the documentary The Aristocrats that to get the role, he slept with Sandler. Stewart often makes fun of his appearances in the high-profile flop, Death to Smoochy, in which he played a treacherous television executive; and the animated film Doogal, where he voiced the villain Zeebad. In 2007, Stewart made a cameo appearance as himself in Evan Almighty, which starred former Daily Show correspondent Steve Carell. In the movie, Stewart was seen on a television screen in a fictional Daily Show episode poking fun at Carell's character for building an ark.
Until Trevor Noah permanently took over the show in 2015, Stewart hosted almost all airings of the program, except for a few occasions when correspondents such as Stephen Colbert, Rob Corddry, Jason Jones, and Steve Carell subbed for him, and during John Oliver's stint as host during the summer of 2013. Stewart won twenty Primetime Emmy Awards for The Daily Show as either a writer or producer, and two for producing The Colbert Report (2013–14), earning a total of twenty-two Primetime Emmy Awards, the most wins for a male individual. In 2005, Stewart and The Daily Show received the Grammy Award for Best Comedy Album for the audiobook edition of America (The Book): A Citizen's Guide to Democracy Inaction. In 2000 and 2004, the show won two Peabody Awards for its coverage of the US presidential elections in those years, called "Indecision 2000" and "Indecision 2004", respectively.
The show of September 20, 2001, the first show after the attacks of September 11, 2001, began with no introduction. Before this, the introduction included footage of a fly-in toward the World Trade Center and New York City. The first nine minutes of the show included a tearful Stewart discussing his personal view on the event. His remarks ended as follows:The view ... from my apartment ... was the World Trade Center ... and now it's gone, and they attacked it. This symbol of American ingenuity, and strength, and labor, and imagination and commerce, and it is gone. But you know what the view is now? The Statue of Liberty. The view from the South of Manhattan is now the Statue of Liberty. You can't beat that.
In mid-2002, amid rumors that David Letterman was going to switch from CBS to ABC when his contract ran out, Stewart was rumored as Letterman's replacement on CBS. Ultimately, Letterman renewed his contract with CBS.
In late 2002, ABC offered Stewart his own talk show to air right after Nightline. Stewart's contract with The Daily Show was near expiring, and he expressed a strong interest. ABC, however, decided to give another Comedy Central figure, Jimmy Kimmel, the post-Nightline slot. In 2004, Stewart and The Daily Show writing staff released America (The Book): A Citizen's Guide to Democracy Inaction, a mock high-school civics textbook offering insights into the unique American system of government, dissecting its institutions, explaining its history and processes, and satirizing such popular American political precepts as "one man, one vote", "government by the people", and "every vote counts". The book sold millions of copies upon its 2004 release and ended the year as a top-fifteen best seller. He also delivered the commencement address for the class of 2004 at his alma mater, the College of William & Mary. In 2005, Stewart provided the voice of President James A. Garfield for the audiobook version of Sarah Vowell's Assassination Vacation.
In 2005, Comedy Central reached an agreement with Busboy in which Comedy Central would provide financial backing for the production company. Comedy Central has a first-look agreement on all projects, after which Busboy is free to shop them to other networks. The deal spawned the Daily Show spin-off The Colbert Report and its replacement, The Nightly Show with Larry Wilmore. Other projects include the sitcom pilot Three Strikes, the documentary Sportsfan, the series Important Things with Demetri Martin, and the film The Donor. In 2007, Stewart voiced Mort Sinclaire, former TV comedy writer and communist, on Stephen Colbert's audiobook version of I Am America (And So Can You!).
On April 4, 2006, Stewart confronted US Senator John McCain (R-AZ) on The Daily Show about his decision to appear at Liberty University, an institution founded by Jerry Falwell whom McCain previously had denounced as one of the "agents of intolerance". In the interchange, Stewart asked McCain, "You're not freaking out on us? Are you freaking out on us, because if you're freaking out ... and you're going into the crazy base world—are you going into crazy base world?" McCain replied, "Just– just– just a little" and "I'm afraid so." The clip was played on CNN, was noted and discussed in more detail in the blogosphere and was followed up on in the mainstream media.
In 2007, The Daily Show was involved in former correspondent Stephen Colbert's announcement that he would run for president in 2008. In 2008, Stewart appeared on the news program Democracy Now!. A 2008 New York Times story questioned whether he was, in a phrase originally used to describe longtime network news anchor Walter Cronkite, "the most trusted man in America".
On April 28, 2009, during a discussion on torture with Clifford May, Stewart stated that former President Harry S. Truman was a war criminal for his use of the atomic bomb on Japan during World War II. He defended his view moments later: "Here's what I think of the atom bombs. I think if you dropped an atom bomb fifteen miles offshore and you said, 'The next one's coming and hitting you', then I would think it's okay. To drop it on a city, and kill a hundred thousand people? Yeah. I think that's criminal." On April 30, Stewart apologized on his program, and stated he did not believe Truman was a war criminal: "I shouldn't have said that, and I did. So I say right now, no, I don't believe that to be the case. The atomic bomb, a very complicated decision in the context of a horrific war, and I walk that back because it was in my estimation a stupid thing to say."
On September 16, 2010, Stewart and Stephen Colbert announced a rally for October 30, known as the Rally to Restore Sanity and/or Fear. It took place on the National Mall in Washington, D.C., and attracted an estimated 215,000 participants. In December 2010, Stewart was credited by the White House, other media, and political news outlets for bringing awareness of the Republican filibuster on the James Zadroga 9/11 Health and Compensation Act to the public, leading to the ultimate passing of the bill that provides health benefits to first responders whose health has been adversely affected by their work at Ground Zero.
In March 2010, Stewart announced that he had optioned rights to the story of journalist Maziar Bahari, who was imprisoned in Iran for 118 days. On the June 6, 2011, episode of The Daily Show, Stewart again hosted Bahari, and in March 2013, he announced that he was leaving the show for 12 weeks to direct the film version of Bahari's 2011 book, Then They Came For Me. Stewart's screenplay adaptation is Rosewater. It premiered at the September 2014 Toronto International Film Festival, receiving "generally favorable" reviews, and was released to general audiences on November 14, 2014.
In 2010, Stewart and The Daily Show writing staff released a sequel to their first book entitled, Earth (The Book): A Visitor's Guide to the Human Race. The book is meant to serve as a Baedeker travel guide for an alien civilization that discovers Earth after humanity has died out, most likely by its own hands. In April 2010, Comedy Central renewed Stewart's contract to host The Daily Show into 2013. According to a Forbes list of celebrities in 2008, he was earning $14 million a year. The New York Times opined that Stewart is "the modern-day equivalent of Edward R. Murrow" and the UK national newspaper The Independent called him the "satirist-in-chief". In an interview, Senator John McCain described Stewart as "a modern-day Will Rogers and Mark Twain".
On the show of January 10, 2011, Stewart began with a monologue about the shootings in Tucson, Arizona. He said he wished the "ramblings of crazy people didn't in any way resemble how we actually talk to each other on television". Before a commercial break, Stewart told viewers that the show would continue as usual the next night. After the commercial break, the show featured a rerun of a field piece done by Jason Jones two years earlier.
In March 2012, Stewart interviewed Bruce Springsteen for Rolling Stone. Writer Wyatt Cenac said that Stewart cursed him out after Cenac acknowledged he was uncomfortable about a June 2011 Daily Show bit about Republican presidential candidate Herman Cain (reported in July 2015).
In March 2013, it was announced that Stewart would be taking a 12-week hiatus from The Daily Show to direct Rosewater, which is based on the book Then They Came for Me by Maziar Bahari. Beginning June 10, 2013, The Daily Show correspondent John Oliver assumed primary hosting duties during Stewart's break. The TV Guide annual survey for 2013 star salaries showed that Stewart was the highest-paid late night host, making an estimated $25–30 million per year. On July 14, 2014, Stewart interviewed Hillary Clinton about the Middle East. Clinton's condemnations of Hamas led Stewart to ask her: "But don't you think they would look at that though as, they've given a lot of different things a chance and these are the only guys to them that are giving any resistance to what their condition is?" For Gazans living in that situation, he said Hamas could be viewed as "freedom fighters".
During a taping of the show on February 10, 2015, Stewart announced he was leaving The Daily Show. Comedy Central president Michele Ganeless confirmed Stewart's retirement with a statement. Later, it was announced that South African comedian Trevor Noah would succeed Stewart as the host of the show. On April 20, 2015, Stewart indicated that his final show would be on August 6, 2015.
On July 28, 2015, Darren Samuelsohn of Politico reported that, twice, Stewart had been at the White House for previously unreported meetings with President Obama: once in October 2011 and once in February 2014. Michael D. Shear of The New York Times also picked up on the story. Stewart responded on his show by pointing out that the meetings were listed in the president's publicly available visitor log and that he has been asked to meet privately by many prominent individuals, including Roger Ailes of Fox News. He said Obama encouraged him not to make young Americans cynical about their government and Stewart said that he replied that he was "skeptically idealistic".
On June 19, 2015, in the wake of the Charleston Church Shooting, Stewart decided not to write jokes for the opening monologue. Elaborating on his decision, Stewart stated, "I honestly have nothing other than just sadness". Stewart spoke about the racial disparity and injustices in America, saying "The Confederate flag flies over South Carolina ... and the roads are named for Confederate generals" describing it as "racial wallpaper". Instead he designated a large portion of the show to his guest that night Malala Yousafzai, calling her "an incredible inspiration," and that "to be quite honest with you, I don't think there's anyone else in the world I would rather talk to tonight than Malala: So that's what we're going to do. And sorry about no jokes."
On August 5, 2015, Stewart's friend of 30 years, comedian Louis C.K., was selected to be the last guest before the final Daily Show episode with Stewart helming the show. C.K. joked that he was there "representing comedy to say good job".
The hour-long-plus final Daily Show on August 6 featured reunions with former correspondents Stephen Colbert, Steve Carell, John Oliver, Samantha Bee, Hasan Minhaj, Ed Helms, Kristen Schaal, Larry Wilmore, Jessica Williams, Aasif Mandvi, Lewis Black, John Hodgman, Rob Corddry, Olivia Munn, Josh Gad, Michael Che, and Mo Rocca and cameo video clips from people Stewart had targeted over the years, including Hillary Clinton, John McCain, Lindsey Graham, Chris Christie, John Kerry, Chuck Schumer, Bill O'Reilly, Wolf Blitzer, Joe Scarborough, and Mika Brzezinski. During the final episode, there was a pre-taped behind-the-scenes look at the show spoofing the long-take Copacabana scene from Goodfellas, featuring a brief appearance by Martin Scorsese. It concluded with a performance by Bruce Springsteen and the E Street Band.
