It wasn't long after Jon Stewart took over 'The Daily Show' from its first host, Craig Kilborn, that the apparent tie between George W. Bush and Al Gore (and the ensuing recount) resulted in months of comedy fodder that catapulted Stewart to the top of the political-satire heap and made stars out of correspondents Steve Carell and Stephen Colbert.
There wasn't much to laugh about in Jon Stewart's first 'Daily Show' following the 9/11 attacks, and he delivered an emotional monologue. "We’ve had an unendurable pain here. And I just wanted to tell you why I grieve, but why I don’t despair..." said Stewart as his eyes filled with tears.
In 2004, Jon Stewart was on the talk show circuit promoting 'America (The Book') when a stop on CNN's 'Crossfire' turned into a serious spanking as Stewart ripped into the show's hosts, who he called "partisan hacks" engaged in dishonest "theatre" — while appearing on their own show! His angry plea to the 'Crossfire' hosts: "Stop hurting America."
Jim Cramer Smackdown
MSNBC host Jim Cramer probably thought he could handle himself against a comedian, but wasn't prepared when Jon Stewart unleashed his fury to slam Cramer for essentially encouraging viewers to gamble away their life savings on volatile stocks. “I understand you want to make finance entertaining, but it’s not a ****ing game," said Stewart with scorn in Cramer's 2004 appearance. "And when I watch that, I get, I can’t tell you how angry that makes me.”
In 2009, Stewart goofed on the controversy over detainees in Guantanamo Bay by introducing a Muppet-like detainee named Gitmo in a bitingly hilarious 'Sesame Street' spoof.
Colbert To Replace Letterman On 'Late Night'
In 2010, Stewart joined forces with former 'Daily Show' correspondent Stephen Colbert for the "Rally to Restore Sanity and/or Fear," with more than 200,000 people showing up at the National Mall in Washington, D.C., for a blending of Stewart's "Rally to Restore Sanity" and Colbert's competing event, the "March to Keep Fear Alive."
Schooling Glenn Beck
One of the show's most classic bits found Stewart putting his own spin on Glenn Beck's wacky, conspiracy theory-laden Fox News show, devoting more than half the 2010 episode to his hilariously unhinged impersonation Beck that stands among his finest 'Daily Show' moments.
The War on The War on Christmas
Every holiday season, Fox News erupts with angry indignation over the perceived liberal "war on Christmas — and every year, Jon Stewart responds hilariously by goofing on said coverage, a Yuletide tradition that's become as much a part of the season as 'How the Grinch Stole Christmas' and Festivus poles.
One of Stewart's most frequent targets has been Fox News personality Bill O'Reilly, gleefully ripping his more outrageous comments to comedic shreds. The gloves came off when Stewart and O'Reilly went podium to podium in their 2012 debate — The Rumble in the Air-Conditioned Auditorium. As 'USA Today' pointed out, "it may not have been the most important debate of the 2012 presidential election season but it was certainly, so far, the most entertaining."
Malaysian Flight 370
The mysterious disappearance of Malaysian Flight led cable news networks — particularly CNN — down a wild rabbit hole of crazy speculation as they trotted out all manner of useless information and crackpot theories to fill air time while trying to hide the fact there was absolutely nothing to report, other than that the plane was still missing. Stewart mercilessly mocked CNN's coverage, joking that the network did offer up about a minute of good coverage "until they realized, 'Oh s***, we've got 23 hours and 59 minutes left to fill. F*** it, let's go nuts!'"