Background

Jonathan Stuart Liebowitz was born to Jewish parents on November 28, 1962 in New York City and grew up in Lawrenceville, New Jersey. His father, Donald, was a physicist for RCA; his mother, Marion, was a teacher of gifted students. The parents divorced when Jon was eleven, and the boy was raised thereafter by his mother. In 1984 he earned a bachelor’s degree in psychology from the College of William and Mary. “My college career,” Stewart 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 formal education, Liebowitz worked at a number of different jobs including, among others, stints 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 nightclub 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 the Stand-Up NY comedy club 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 rumored to be one of the finalists under consideration to replace David Letterman as the host of NBC’s late-night show, but he lost out to Conan O’Brien. Stewart then became the 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.

Stewart played a minor character in the 1994 film Mixed Nuts, and shortly after his TV show’s demise in the mid-’90s he signed a contract with Miramax to perform in movies. He thereafter appeared in a variety of films, including Wishful Thinking (1997), Half Baked (1998), Since You’ve Been Gone (1998), The Faculty (1998), Playing by Heart (1998), Big Daddy (1999), Committed (2000), Death to Smoochy (2002), and others.

“My Comedy Is Informed by an Ideological Background”

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….”

Stewart the Socialist

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 after Ailes had made his statement, 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 Books

In 2004 Stewart and his team of Daily Show comedian-reporters published their own book, America (The Book): A Citizen’s Guide to Democracy Inaction. This book made best-seller lists despite being banned from some stores because it included a fake photograph that purported to show the members of the U.S. Supreme Court naked. This same gimmick had been used in Jon Stewart’s first book, Naked Pictures of Famous People (1998). In 2010, Stewart again collaborated with other Daily Show writers to publish Earth (The Book): A Visitor’s Guide to the Human Race.

Popularity of The Daily Show

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.”

Ending The Daily Show and Signing a Deal with HBO

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.

Stewart then 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.

Secret Consultations with President Obama

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. As Politico reported on July 28, 2015:

“Jon Stewart slipped unnoticed into the White House in the midst of the October 2011 budget fight, summoned to an Oval Office coffee with President Barack Obama that he jokingly told his escort felt like being called into the principal’s office.

“In February 2014, Obama again requested Stewart make the trip from Manhattan to the White House, this time for a midmorning visit hours before the president would go before television cameras to warn Russia that ‘there will be costs’ if it made any further military intervention in Ukraine.

“To engage privately with the president in his inner sanctum at two sensitive moments — previously unreported meetings that are listed in the White House visitor logs and confirmed to POLITICO by three former Obama aides — speaks volumes about Stewart and his reach, which goes well beyond the million or so viewers who tune in to The Daily Show on most weeknights.”

Criticisms of Israel

Stewart’s tendency to criticize and/or mock Israel have been particularly controversial over the years. For example:

• During a three-week battle between Hamas and the Israeli military in January 2009, Stewart referred to the civilian casualties suffered by the Palestinians of Gaza as a “civilian carnage Toyotathon.”
• In September 2011, Stewart said that Palestinian efforts to gain membership in the United Nations might be more successful if they were to change the spelling of their homeland to “Palestein,” mimicking a common Ashkenazi Jewish spelling. Or better yet, he suggested: “Dr. Murray Palestein.”
• In November 2013, Stewart opined that Israel’s policies vis-a-vis the Palestinians were freighted with overreaction to the legacy of Jewish oppression: “The danger of oppression is not just being oppressed, it’s becoming an oppressor.”
• In July 2014, when the Israeli military was trying to dismantle Hamas’s vast terrorist infrastructure in the Gaza Strip, Stewart lamented that “the humanitarian crisis in Gaza is overwhelming,” emphasized that “the world must do more for the people who are trapped by this conflict,” and explained that the Palestinian people understandably viewed Hamas militants as “freedom fighters.” Stewart also noted that “most Hamas rockets are neutralized by Israel’s Iron Dome technology, and Israeli citizens can even now download a warning app” to their cell phones, to alert them to incoming missiles. He joked that, by contrast, “the Israeli military warns Gaza residents of imminent bombing, with a smaller warning bombing! An amuse-boom, if you will.” Reacting to a film clip of a Gazan family recounting how the Israeli military had instructed them to evacuate their home prior to an imminent air raid, Stewart displayed a map of the region and exclaimed: “Evacuate to where?! Have you fucking seen Gaza?! It’s this big [i.e., tiny]. Israel blocked this border. Egypt blocked this border. What, are they supposed to swim for it?”
• In August 2015, the Palestinian-American comedian and law professor Amer Zahr lauded Stewart, saying: “[F]or the past 15 years or so, amid a sea of bias and distortion, one voice in the American media has given some modicum of balance to discussion on the Palestinian question. One individual has humanized Palestinian lives and leveled the debate. One personality has dared to criticize Israeli policies that have for so long denied the most basic of rights to Palestinians, through occupation and ethnic supremacy. One man. One American…. Jon Stewart. Whether Jon Stewart knows it or not, and whether he likes it or not, he has become a bit of a hero to us Palestinians over the years. We incessantly share and pass along clips of his bits.”
• At daybreak on October 7, 2023 — which was the major Jewish holiday of Simchat Torah — the Islamic terror group Hamas carried out a massive, multi-front, surprise attack against Israel, firing thousands of rockets from Gaza into the Jewish state, while dozens of Hamas fighters infiltrated the Israeli border in a number of locations by air, land and sea. The attack had been planned in conjunction with officers from Iran’s Islamic Revolutionary Guard Corps, along with agents of three other Iran-sponsored terrorist groups. By October 8, at least 600 Israelis had been killed and 1,800 wounded, making it the bloodiest day Jews had experienced since the Holocaust. Moreover, Hamas took more than 240 Israelis hostage, including dozens who were American citizens, and moved them to the Gaza Strip. By October 19, the official casualty toll in Israel had reached more than 1,400 dead (including at least 32 Americans) and 4,500 injured. On October 27, 2023, the Israeli Defense Forces (IDF) launched an invasion of the Gaza Strip with the stated aim of destroying Hamas and its leadership once and for all. On February 26, 2024, Stewart devoted his monologue on The Daily Show to criticizing Israel’s military response to the Hamas terror attack, and mocking the respective administrations of President Biden and Israeli Prime Minister Benjamin Netanyahu:
  

  “Well, folks, this is an awful situation. We’re coming off on five months of a brutal bombing campaign brought on by a horrific massacre and hostage taking…. Well, this weekend, Israeli Prime Minister, Benjamin Netanyahu, finally laid out his plan for peace. Benjamin Netanyahu is calling for complete demilitarization of Gaza, as well as Israel taking over security and controlling entry and exit points to Gaza. So your peace plan is a siege, a military siege. You really think a military solution ends this cycle?

  “Well, victory is within reach, and you can’t have victory until you eliminate Hamas. But, okay. But your plan to eliminate Hamas by destroying all of Gaza, doesn’t that just make more Hamases? Is that the plural of Hamas? Hamasai? I mean, it’s an idea. Palestinian liberation is an idea. Unless you have a bomb that kills ideas, do you have a bomb that kills ideas? I mean, how long would it even take to bomb this shit out of an idea?…

  “Oh, dear God. If you insist on this plan, if you think that ends Hamas, I believe we in the United States have a banner you can use [a reference to former President Bush’s much-maligned ‘Mission Accomplished‘ banner from 2003]. It’s a little wind-damaged, but equally delusional….

  “This is shameful. There has to be accountability for these war crimes. No targeting civilians in war. Stop the war crimes and the atrocities and end the war today…. Israel must do more to protect innocent civilians. We want to see the government of Israel take steps to minimize civilian harm. Be more surgical and more precise…. Doesn’t anyone care about the suffering of all these civilians? … The Palestinian cause is the Arab world’s most important cause.

  “I want to see really a good life for the Palestinians…. Israel, the United States, the United Nations, the Arab Nations, no one seems to be incentivized to stop the suffering of the innocent people in this region.”

Portraying America as a Racist Nation

On June 19, 2015, Stewart spoke about a mass killing recently perpetrated by a 21-year-old gunman named Dylann Roof, white supremacist who had shot and killed nine black people and wounded a tenth at a Bible study meeting in the Emanuel African Methodist Episcopal Church in Charleston, South Carolina. He used the story to characterize America as a nation infested with white racism. Some key quotes:

• “I have nothing other than just sadness that once again we have to peer into the abyss of the depraved violence that we do to each other, and the nexus of a just gaping racial wound that will not heal but we pretend doesn’t exist. I’m confident, though, that by acknowledging it, by staring into that and seeing it for what it is, we still won’t do jackshit. Yeah. That’s us.”

• “I heard someone on the news say, a tragedy has visited this church. This wasn’t a tornado. This was racist. This was a guy with a Rhodesia badge on his sweater. This one is black and white. There’s no nuance here. And we’re going to keep pretending: I don’t get it, what happened, there’s one guy lost his mind. We are steeped in that culture in this country and we refuse to recognize it, and I cannot believe how hard people are working to discount it.”

• Referencing what he called the “racial wallpaper” of South Carolina, where a confederate flag was situated within the grounds of the state’s capitol building, Stewart said: “The confederate flag flies over South Carolina. And the roads are named for Confederate generals. And the white guy’s the one who feels like his country’s being taken away from him.”

In June 2020 — about three weeks after the infamous death of George Floyd during an encounter with police officers in Minneapolis — Stewart said in an interview with The New York Times:

• “The police are a reflection of a society. They’re not a rogue alien organization that came to torment the black community. They’re enforcing segregation. The police are, in some respects, a border patrol, they patrol the border between the two Americas.”
• “There’s not a white person out there who would want to be treated [by police] like even a successful black person in this country. And if we don’t address the why of that treatment, the how is just window dressing. The policing is an issue, but it’s the least of it. We use the police as surrogates to quarantine these racial and economic inequalities so that we don’t have to deal with them.”

Later that month, during the June 24, 2020 episode of The Late Show, Stewart speculated as to why the George Floyd protests had erupted in cities across the United States during that particular time period. “In some respects,” he said, “I wonder if the [coronavirus] pandemic, because we all went into kind of a stasis, and so much of our — the distractions of your daily life were removed, that it allowed the country a moment of clarity…. It’s almost like in this moment of more quiet reflection, America suddenly stopped and smelled the racism. Do you know what I mean? There was that feeling that we were in a moment’s pause, and in that one breath, maybe it suddenly became clear.”

During a March 26, 2023 appearance on CNN, Stewart told host Fareed Zakaria that efforts to promote Critical Race Theory and “Diversity, Equity & Inclusion” initiatives were noble but insufficient. “The diversity and equity initiatives are a salve,” he said. “They are to pacify and mollify because we won’t actually do the real thing. We won’t actually dismantle the vestiges of all the systemic racism and all this systemic classism and all the systemic gender issues. We won’t actually dismantle that. But what we will do is you can have an office in the building. And every few months we’re going to have to sit and listen to you talk for like an hour. And so we’re good, right?”

Low Journalistic Standards

In a November 2015 article, National Review Online criticized Stewart for his “dubious journalistic standards.” In the following excerpts from that article, are some examples of people who claim to have been victimized by those low standards:

• Peter Schiff: “The financial analyst and libertarian radio host told Mediaite that a four-hour interview about his opposition to raising the minimum wage with Daily Show correspondent Samantha Bee was misleadingly spliced together to make him appear uncaring for those in poverty and the mentally disabled. To make matters worse, the commentator brought in to the segment to argue for raising the minimum wage, equities analyst Barry Ritholtz, said that he was allowed multiple takes on certain questions, an opportunity Schiff suggests he was not afforded.”
• Nolan Finley: “In November of [2014], the Detroit News columnist wrote about his experience on the late-night show. In the midst of controversy over the city’s decision to shut off water to residents who failed to pay their bills, Finley explained that he went in to great detail with correspondent Jessica Williams about the various economic and social problems facing the Motor City, and how they led to the shutoffs. When Williams pointed out that the city’s stadiums and arenas still have water despite not paying their bills, Finley agreed that their water should be shut off too. But when the segment aired, it buried the complexities of Finley’s argument, instead casting him as a foil to those fighting against the shutoffs, and a staunch defender of denying water to residents.”
• Washington Redskins Football Fans: “Amid controversy over the name of the Washington Redskins, correspondent Jason Jones sat down with four fans of the team to discuss why they opposed changing the name. But according to the Washington Post, the conversation quickly turned from playful and lighthearted to the point where one fan ‘felt in danger’ and was driven to tears, after Jones ambushed the four interviewees with a group of American Indians who confronted them about the name. Another fan said the show’s producers misled them about the premise of the segment, saying they would hold separate interviews with those favoring the name and those opposing it, and offering assurances that there would be no cross-panel discussion.”
• San Bernardino District Attorney Mike Ramos: “In making the case that the killing of Michael Brown in Ferguson, Mo. was not an isolated incident, Stewart included Dante Parker on a list of unarmed black men killed by law enforcement. But Parker’s death was not as simple as Stewart claimed, and Ramos took to YouTube to criticize the show for failing to do its homework: Parker died of a PCP overdose, according to a coroner, and he was tased — not shot. Stewart ultimately went on to issue a retraction, and apologize to Ramos and the county’s officers​.”

Contempt for Conservatives

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.”

Contempt for Donald Trump & His Allies

During the 2016 presidential campaign between Donald Trump and Hillary Clinton, Stewart pledged to move out of the United States if Trump were to win the election.

In early June 2018, Stewart came to the defense of comedienne and TBS late-night host Samantha Bee, after the latter was widely criticized for having called White House advisor Ivanka Trump a “feckless cunt.” “They don’t give a shit about the word ‘cunt,’” Stewart said of President Trump and his administration during a June 3rd Q&A session at the Clusterfest comedy festival. “That is probably—he says that instead of ‘please,’ I’m guessing,” Stewart continued, adding that there was nothing anyone could do to “make them give up this ‘We’re the real victims’ game,” because “it’s a game, it’s a strategy, and it’s working.”

During the June 28, 2018 edition of The Late Show, Stewart addressed President Trump with some pointed remarks deriding the latter for his allegedly bad character. Among Stewart’s remarks were the following:

• “Hello, Donald. It’s me, the guy you made sure everyone knew was Jewish on Twitter [a reference to an old Twitter feud between Stewart and Trump]. I know you’re upset about all the criticism you’ve been taking in the ‘fake news’ and the ‘fake late-night shows.’ It’s just that we’re still having a little trouble adjusting to your presidency as it goes into its 500th year.”
• “Everything’s off its axis, it’s a little unusual. Apparently, Putin and Kim Jong Un are noble, intelligent role models, and Canada’s a bunch of giant assholes. If there’s one hallmark to your presidency that I think we’re finding most difficult, it’s that, no matter what you do, it always comes with an extra layer of gleeful cruelty and dickishness.”
• “For an end to this gratuitous dickishness, what can we give you? You dig the dictator thing. How about a giant building with gold toilets and your name on it? Clearly, we’re not going to be able to negotiate or shame you into decency, but there is one place where I draw the line: I won’t allow you and your sycophants to turn your cruelty into virtue.”

While Stewart made a June 29, 2020 appearance on ABC’s The View, co-host Whoopi Goldberg referenced a recent incident where Trump had retweeted a video in which some people claiming to be his supporters shouted the words “white power.” “Just out of curiosity,” Goldberg asked Stewart, “[do] you think he couldn’t hear or didn’t hear what was being said? Maybe he had, you know, wax in his ear or something?” Stewart replied: “No. I think, just, white power is playing in his head all the time. So he hears it from somewhere else, he just thinks —I think it’s just like Muzak, just kind of playing in his head all the time, so he doesn’t really listen to it.”

Advocating in Favor of Transgender Medical Procedures for Minors

On October 7, 2022, the Twitter account of Stewart’s show The Problem With Jon Stewart — which aired from October 2022 to October 2023 — released a six-minute video of Stewart conducting a combative interview with Arkansas’ Republican Attorney General Leslie Rutledge. In that interview, Stewart claimed that Rutledge and others who were opposed to permitting minors to undergo gender-transition procedures such as cross-sex hormone injections, mastectomies, hysterectomies, and orchiectomies, were irresponsibly ignoring vital guidelines that prominent “medical organizations” had established for the purpose of saving the lives and psyches of children with gender dysphoria. “Why would the state of Arkansas step in to override the parents, physicians, psychiatrists, endocrinologists who have developed guidelines?” Stewart asked Rutledge. “Why would you override those guidelines?” Stating also that “the American Medical Association, the American Academy of Pediatrics, and the Endocrine Society” had all endorsed such procedures for children with gender dysphoria, he challenged Rutledge by asking: “What are your qualifications to step in and say, ‘No. Keeping you from [transgender treatment] is protecting you’?”

When Rutledge countered by noting that  “98%” of children who express gender dysphoria eventually grow out of the condition after they undergo counseling and other non-medicinal, non-surgical interventions, Stewart retorted: “Wow. That is an incredibly made-up figure.”

At one point Stewart went so far as to liken transgender treatments for minors to “chemotherapy” treatments for cancer patients: “So, if your child is suffering from pediatric cancer, and the state comes in and says to you, ‘They recommend chemotherapy, but we’re not going to let you do that. You can’t. We think you should get a different opinion, and here’s the organization we think you should get the opinion from…. Does that sound like something you would accept?” “Parents with children who have gender dysphoria have lost children to suicide and depression,” added Stewart. “Because it’s acute.”

Returning to Host The Daily Show Once Per Week

In January 2024, it was announced that Stewart, starting February 12, would return to host and produce Comedy Central’s The Daily Show on Monday nights throughout the 2024 U.S. elections cycle. On the other nights of the week, the program would be hosted by a rotating line-up of regulars.

Mocking the Notion That Illegal-Alien Crime Rates Should Concern Americans

During the March 4, 2024 episode of The Daily Show, Stewart dismissed Republicans’ professed concerns about violent crimes committed by illegal aliens, as nothing more than election-year fear-mongering over a non-issue. “Yes, every two to four years we are reminded that we have a southern border, and it is porous,” he said sarcastically while looking into the camera and feigning terror. At one point, Stewart suggested that the practice of allowing massive numbers of migrants to enter the U.S. illegally was simply one of the nation’s “unshakeable, bedrock American values.” “When it comes to immigration, the Democrats hold to our country’s cherished ideals, the eternal promise etched at the feet of Lady Liberty that speak to our better angels,” Stewart added, making no distinction between legal and illegal newcomers.

Stewart’s Hypocrisy Regarding the Valuation of Homes & Properties

During the March 25, 2024 episode of The Daily Show, Stewart derisively accused former President Trump of “lying” about the valuation of some of his properties — “shenanigans” that, by Stewart’s telling “cost the city of New York.” Specifically, Stewart was referring to the fact that NY Attorney General Letitia James had filed a civil lawsuit accusing Trump of exaggerating the value of his assets by at least $3.6 billion per year in order to secure favorable loan-interest rates from banks. Conversely, noted Stewart, “The attorney general … knew that Trump’s property values were inflated because when it came time to pay taxes, Trump undervalued the very same properties. It was all part of a very specific real estate practice known as lying.”

But documents obtained by the New York Post showed that Stewart himelf in 2014 had overvalued his own New York City home by more than $16 million when he sold his 6,280-square-foot Tribeca duplex for $17.5 million, though 2013-14 assessor records placed the estimated market value of the home at only $1.882 million, and the actual assessor valuation for property-tax purposes was a mere $847,174. As Breitbart.com put it: “Stewart paid property taxes based on that assessor valuation price — in other words, what he accused Trump of doing.”

When critics pointed out Stewart’s hypocrisy regarding this matter, he posted the following sarcastic response on his X social-media account: “OMG!! I’ve been caught doing something not remotely similar to Trump! I guess all I need to do now is start a fraud college, steal classified docs, bankrupt casinos, pay hush money, grab pussies, discriminate in housing, cheat at golf and foment insurrection and you’ll revere me!”

Stewart’s Massive Wealth

As of April 2024, Stewart had a net worth of approximately $120 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.