Top 10 Times Jon Stewart Best Explained Something

“The Problem with Jon Stewart” (2021-23)
In the season 2 premiere of “The Problem with Jon Stewart,” Jon takes on the public debate over gender identity. The entire episode is dedicated to examining the right-wing moral panic over trans people and the gender binary. He engages a panel of experts to break down - in granular detail - how gender affirming care does and does not work. The evangelical right spreads a great deal of misinformation about trans people, so Stewart uses the episode to lay those bad-faith arguments bare. As part of that effort, he interviews the Arkansas Attorney General Leslie Rutledge, who has supported a raft of anti-trans actions and laws. His probing questions belie the factless arguments justifying those laws.

“The Daily Show” (1996-)
Americans have garnered an infamous reputation for being ignorant of world events. In June 2009, Jon Stewart and his faux news team decided to remedy that. Much of their coverage that month was dedicated to the presidential election in Iran. One of America’s geopolitical foes, Jon - and his on-the-ground correspondent Jason Jones - set out to disabuse Americans of their prejudices. They investigated, in depth, both the election and everyday lives of Iranians. They covered the politics leading up to the election as well as the Green Revolution protests afterwards. Knowing that large swathes of the public received their news from "The Daily Show," Jon used his platform to educate America on an important world event they would otherwise have not learned about at all.

“The Daily Show” (1996-)
In the wake of the 2008 Recession, the American people demanded both help and answers. Jon Stewart met the moment, devoting multiple segments to an under-examined aspect of the crash: CNBC. Jon spent multiple episodes examining the financial network’s coverage and advice. Their financial analysts were often flat out wrong on the facts even as they promoted risky trading behavior. They treated the markets like a sport, encouraging everyday people to invest. When the economy crashed, these same analysts were bullish on bailouts for wall street while slamming bailouts for main street as handouts to the undeserving. Stewart flashed a bright light on the absolute hypocrisy of this position, bashing whiny traders. It culminated with a brutal takedown interview with CNBC star Jim Cramer.

“The Daily Show” (1996-)
Throughout his first run as the host of “The Daily Show,” Jon often brought up the extrajudicial prison, Guantanamo Bay. He covered its initial use under George W. Bush, as well as Obama’s failed promise to close the prison. Stewart didn’t pull any punches, spending multiple segments over many years examining the institutional hurdles to closing the base. In his view, America sacrificed too many civil liberties in the War on Terror. We built an American gulag, replete with 'enhanced interrogation' and permanent detention. He was honest, also acknowledging that some of these prisoners were, in fact, terrorists: freeing them would be incredibly dangerous. Ultimately, Stewart sticks to his guns. In his estimation, making America less free doesn't necessarily make us more safe.

“The Daily Show” (1996-)
Jon’s first viral foray into the Israel/Palestine conflict came in 2014 during an Israeli incursion into Gaza. As a player in the leftist political space - and a Jewish American - Stewart attempted to navigate the incredibly uncomfortable conversations on the subject. For Jon, knee-jerk American reactions tend to be too oversimplified. For decades, politicians of both parties were essentially 'not allowed' to question Israel's policies vis a vis Palestine. Conversely, the voices on the left tend to be monomaniacal, refusing to engage in anything other than personal attacks on people who disagree. A decade later, during another Israeli invasion, Jon tackled the topic amidst the cacophony of hot takes. He did a deep dive into all the involved parties and potential solutions.

“The Problem with Jon Stewart” (2021-23)
Donald Trump and the GOP have sounded the alarm bells about ‘election integrity’ for years. They have claimed, without evidence, that the 2020 presidential election was fraudulent. In Republican-controlled states, ‘election integrity’ has been a casus belli for draconian voting restrictions. Worse, it’s led to intimidation and threats of violence against election workers. One lie - The Big Lie - has had real-world negative impact on people across America. Jon caps his examination with a viral interview with Arizona Attorney General Mark Brnovich. The entire episode and interview highlight the circular logic at work: politicians pushing this line mislead about voter fraud, which in turn gins up their base who now think that it's a massive problem.

“The Problem with Jon Stewart” (2021-23)
Jon Stewart has never shied away from the gun debate. During his first run on “The Daily Show,” he covered one mass shooting after another, slamming lawmakers for their inaction. He tackled the issue again in “The Problem with Jon Stewart.” In yet another viral interview, Jon debated gun-supporting state Senator Nathan Dahm from Oklahoma. He proved once again his uncanny ability to strip someone’s beliefs to the bone, putting all of the flaws and hypocrisy on full display. Stewart argued that an unregulated market for guns causes mass death. He listened to Senator Dahm’s talking points - arguments used by lobbyists to prevent gun laws for decades. He replied with facts and figures to explain to his viewers just how solvable this problem could be.

“The Daily Show” (1996-)
In 2009, opponents of the Affordable Care Act were adamant in their opposition. For months leading up to its passage and for years afterwards, they used exaggerations and outright lies to stoke public fear. One frequent false claim was that government death panels would be established to decide people's fates. One such critic, former New York Lieutenant Governor Betsy McCaughey, went to “The Daily Show” to voice her concerns. The pair clashed on the bill's fine-tooth details, details that were too often lost in the noise of politics. He poked holes in many of her arguments, highlighting the truth. After the bill’s passage, he would keep lawmakers honest by bringing on the HHS Secretary and even President Obama to illustrate problems with the ACA’s implementation.

“Crossfire” (1982-2005; 2013-14)
Jon Stewart's appearance on "Crossfire" in 2004 was a pivotal moment in both media criticism and American political discourse. As a guest, Stewart slammed the show's hosts for their partisan bickering. He argued that the political media, by turning politics into gladiatorial combat, had done a disservice to the world. His critiques resonated with many viewers who were exhausted by sensationalized news coverage. His powerful words ultimately led to the show's cancellation. Stewart advocated for responsible journalism, and cemented his role as a sort of watchdog for the media. It’s a hobby horse he has ridden again and again in the last two decades. Stewart's appearance on "Crossfire" became a teaching moment about media ethics, bias, and the role of journalists in holding politicians accountable.

“The Daily Show” (1996-)
Jon Stewart fans know that he's long been a steadfast advocate for 9/11 first responders. It began with a 2010 episode of “The Daily Show,” where Stewart pushed for passage of The James Zadroga 9/11 Health and Compensation Act. The law was designed to provide funds for health monitoring and aid to all of those who suffered health complications from their response to the September 11th attacks. At the end of 2010, Republican senators were filibustering the bill. To combat their spin, Stewart brought on a panel of first responders to explain both why the bill was necessary, and to shame lawmakers into passage. Since then Stewart has led the charge to guarantee its reauthorization, as well as those of similar laws.

Did Jon Stewart ever help you learn a lot while he made you laugh? Were any of his best lessons left off of our list? Let us know in the comments below!