10. Rally to Restore Sanity
The Daily Show has consistently targeted politicians and journalists who promote polarizing, alarmist viewpoints to further their own agendas and ratings. Stewart’s frustration with the extremes of political debate was the impetus for the 2010 Rally to Restore Sanity, co-hosted by Stephen Colbert. The event drew more than 200,000 people to the National Mall in Washington, D.C., and included performances by Ozzy Osbourne, Kid Rock, Cat Stevens, The Roots, Tony Bennet, and others.
Stewart closed the event with a speech in praise of reasonableness, invoking the image of drivers waiting in line at a tunnel, merging together, one small compromise at a time.
“Because we know instinctively as a people that if we are to get through the darkness and back into the light, we have to work together. And the truth is, there will always be darkness. And sometimes, the light at the end of the tunnel isn’t the promised land. Sometimes, it’s just New Jersey,” Stewart said. “But we do it anyway, together.”
9. Cheney’s Got a Gun
If you are looking for a moment of pure glee, it’s hard to beat Stewart’s segment on Vice President Dick Cheney’s accidental shooting of a fellow quail hunter in 2006.
8. Anthony Weiner
Jon Stewart and ill-fated mayoral candidate Anthony Weiner are old friends and former roommates, but when Weiner’s dick-pic scandal broke, Stewart didn’t let their friendship get in the way of the comedy. One of the best moments was Stewart’s parody of Weiner’s resignation press conference, when Stewart apologized for not making enough Weiner jokes and accidentally gashed his hand while making a blender of frozen margaritas.
7. Koch Brothers
In 2014, Koch Industries bought some ad time on The Daily Show. Stewart took the opportunity to do a segment on the Koch brothers, and then parodied the ad by adding a new voiceover from Samantha Bee:
“With our heartfelt devotion to fossil fuels, we make your planet warmer, and your water more flammable, while lubricating your birds and re-arranging your polar bears.”
6. Bush vs. Bush
In the age of the 24-hour news cycle and Twitter-length attention spans, The Daily Show excels at exposing hypocrisy and insincerity by confronting politicians with their own words. One of the best examples is the debate over American adventurism the show staged between President Bush and Governor Bush.
5. Pervez Musharraf
Pakistan’s President Pervez Musharraf first stopped by The Daily Show in 2006, and Stewart served him tea, Twinkies, and a difficult question.
“Where is Osama bin Laden?” Stewart asked Musharraf, who narrowly avoided a spit-take.
4. Glenn Beck
Over the years, Glenn Beck has provided a lot of fodder for the Daily Show’s hay-making machine. The authoritative bit is Stewart’s exhaustive 2010 takedown, when he plumbed the depths of Beck’s paranoid style for almost 15 minutes. The glasses, the hand waving, the crazy chalkboard scribbling—Stewart used Beck’s own tools and absurd logic against him.
3. Pizza Etiquette
New York City pizza has many devotees, but none so unhinged in their obsession as Jon Stewart. His interpretation of pizza etiquette is strict and straightforward: above all else, knives and forks are verboten. If Emily Post had a mob enforcer, it would be Jon Stewart, whose angry public shaming of those who ignore the rules is as satisfying as a fresh slice. Donald Trump was the original violator. In 2012, Trump took Sara Palin to a Times Square chain, his first demerit—but then he picked up a fork.
Just last year, when de Blasio made the mistake of “trumping” his pizza, Stewart didn’t let is slide.
2. Trump for President
Donald Trump’s entry into the Republican presidential race was a parting gift for Stewart, who described Trump’s announcement speech as “the most beautiful jibber-jabber ever to pour forth from the mouth of a bat-shit billionaire.”
With Trump in and Stewart out, how will we survive?
1. O’Reilly vs. Stewart
Stewart’s verbal spars with O’Reilly are always fun to watch, partly because they both seem to enjoy each other. In this clip from 2014, Stewart tried to get O’Reilly to admit that white privilege exists.
If you want more, there’s the full 90-minute debate the two did at George Washington University in 2012.