Jonathan Stuart Liebowitz was born to Jewish parents on November 28, 1962 in New York City and grew up in Lawrenceville, New Jersey. In 1984 he earned a psychology degree from the College of William and Mary. “My college career,” he later told New York Magazine, “was waking up late, memorizing someone else's notes, doing bong hits, and going to soccer practice.”
After completing his education, Liebowitz worked variously as a cancer research laboratory staffer, a bartender, a contract administrator for CUNY, a puppeteer for disabled children, and a van driver for a catering company. In 1987 he performed his first public comedy routine during an “open-microphone night” at the Bitter End Club in New York. Regarding his use of the stage name “Jon Stewart,” Liebowitz later explained: “I'm not a self-hating Jew. Actually, to borrow a line from Lenny Bruce, I just thought Leibowitz was too Hollywood.”
Stewart soon found regular work as a comedian at Stand-Up NY and then at Caesar's Palace. By 1989 he began appearing on television as the host of Comedy Central's Short Attention Span Theater, and in 1992 he hosted MTV's You Wrote It, You Watch It. In 1993 Stewart was one of the finalists under consideration to replace David Letterman as the host of NBC's late-night show, but lost out to Conan O'Brien. Stewart then became host of MTV's The Jon Stewart Show, which was canceled after one season because of low ratings. In 1994 the Viacom-owned company Paramount gave Stewart his own syndicated program, but poor ratings likewise led to its cancellation the following year.
When Stewart replaced comic Craig Kilborn as anchorman (and co-executive producer) of Comedy Central's The Daily Show in January 1999, he reshaped this parody of network newscasts to suit his own unique style. Stewart's brand of humor tends to be relatively gentle when poking fun at Democrats, but more pointed with regard to Republicans. His chief criticism of Democrats is that they are not liberal enough, or that they oppose Republicans too timidly. “My comedy is informed by an ideological background, there's no question about that,” Stewart said in 2011. “There's no question I don't tell the full story....”
When broadcaster Larry King told Stewart “I think you’re a Democrat” during a December 2000 interview on CNN, Stewart replied: “I think that’s probably correct. I would say I’m more of a socialist or an independent.” Years later, in May 2012, Fox News chairman Roger Ailes said that Stewart, in a private conversation, “basically has admitted to me ... that he’s a socialist.” Soon thereafter, Stewart addressed the matter on his program, saying: “I don’t believe in state control of industry or collectivizing farms, but I do believe that there is value in some policies that derive from a more socialist ethos, like, uh, um …” At that point, he cut to film footage of Mitt Romney describing Social Security as “an essential program,” and Sarah Palin lauding Medicare. “Can’t we just admit a socialist is someone who wants to spend government money on things you don’t like?” Stewart concluded.
Stewart's Daily Show consistently ranked as one of television's most popular programs among the 18-34 age demographic. As Boston Globe reporter Don Aucoin once put it, “What Walter Cronkite was to an earlier generation—an utterly trusted voice—Stewart has been to millennials.” A National Review analysis observed that Stewart “provides intellectually lazy people with an excuse for forgoing the hard work of informing themselves at anything but the most superficial level about political events.”
Stewart took a break from The Daily Show for a few months in 2013 in order to direct the film Rosewater, and then returned to his program that September. He voluntarily resigned from the show on August 6, 2015, and three months later he announced that he had signed a four-year deal to create digital content for HBO platforms.
President Barack Obama valued Stewart as an adviser and confidante, twice inviting him to the White House (in October 2011 and February 2014) for secret consultations.
Stewart's tendency to criticize and/or mock Israel have been particularly controversial over the years. For example:
In a May 2016 interview with David Axelrod, Stewart said the following about conservatives: "As far as I can tell, the conservative side, or the right side, they feel an ownership over America. They are the stewards of America. They are its forbears — exactly. Republicans, conservatives love America. They just hate, like, 50 percent of the people living in it." Moreover, he claimed that their "nativism" had caused them to support presidential candidate Donald Trump, who, by Stewart's telling, was preaching that Muslims "[are] evil and shouldn’t be allowed in this country." Regarding Trump's pledge to "make America great again, Stewart said: "When was America great? What is this time that he speaks of? ‘81 to ‘82? Like, what are we talking about? And who took your country away from you?... Who’s country is it? Take up the argument with the Founders. Take it up with the Age of Reason. That's --- All men are created equal. That’s fucked the whole thing up."
Stewart today has a net worth of approximately $80 million. In 2014 he sold his 6,000-square-foot New York City penthouse for $17.5 million. The Daily Caller reports that Stewart, “using a trick mastered by countless one-percenters,” has generally purchased his homes through private trusts, in order to protect the houses from lawsuits and minimize his estate-tax liability.
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