This may be remembered as the definitive moment of Stewart’s run on The Daily Show. In the first show back after the September 11 terrorist attacks, Stewart began the show with this truly special monologue, fighting through tears to deliver it. Americans were looking for someone to tell them it would be okay, and Stewart did just that. “The view from my apartment was the World Trade Center—and now it’s gone. This symbol of American ingenuity, and strength, and labor, and imagination and commerce, and it is gone,” he said. “But you know what the view is now? The Statue of Liberty. You can’t beat that.”

Interview with Jim Cramer

In 2009, Stewart interviewed CNBC financial pundit Jim Cramer about the 2008 financial crisis. Stewart, visibly angry, accused Cramer, his network CNBC, and other financial analysts of lulling the American public into a false sense of security even as they knew what was going on behind closed doors on Wall Street. “You knew what the banks were doing, and yet were touting it for months and months,” he said. “[That’s] disingenuous at best, and criminal at worst.”

Remarks on Charlie Hebdo

Following the Charlie Hebdo attacks in Paris, Stewart opened his show with a somber, pointed commentary on the role of comedy in our everyday lives. “This is a stark reminder that, for the most part, the legislators and journalists and institutions that we jab and ridicule are not in any way the enemy,” he said.

Advocating for the 9/11 first responders’ health bill

The James Zadroga Act was created to provide treatment and testing to 9/11 first responders, many of whom developed cancer and other serious diseases directly attributed to working in the rubble. The bill, however, was stuck in US Congress as Republicans in the Senate filibustered it. Stewart is credited with raising awareness for the bill and ultimately getting it passed. ”We had hit a brick wall in the Senate. Nothing was working. And then Jon Stewart really took it up. And I distinctly remember the impact that he had,” New York congresswomen Carolyn Maloney told the New York Times. “It was Jon Stewart who brought that bill to life.”

Reaction to the Eric Garner grand jury decision

In December 2014, a Staten Island grand jury decided not to indict the police officer who put Eric Garner in a chokehold, ultimately leading to Garner’s death. Stewart articulated the feelings of many: a sense of hopelessness, disillusionment, and anger. ”If comedy is tragedy plus time, I need more fucking time,” Stewart declared. “But I would really settle for less fucking tragedy, to be honest with you.”

Reaction to the Charleston massacre

Not that Stewart ever shied away from saying what he felt, but clearly sensing that his time as host of The Daily Show was ending, Stewart delivered one of his most earnest monologues ever following the massacre of nine black people by a white supremacist in a church in Charleston, South Carolina. Most of Stewart’s comments were obviously unscripted.

“I honestly have nothing, other than just sadness, once again, that we have to peer into the abyss of the depraved violence that we do to each other in the nexus of a gaping racial wound that will not heal, yet we pretend doesn’t exist.”

“We still won’t do jack shit,” he said. “Yeah, that’s us.”

Honorable mention—the infamous appearance on CNN’s Crossfire

While this technically isn’t from The Daily Show, it was one of Stewart’s best moments on TV. He appeared on the CNN debate show Crossfire—hosted by liberal Paul Begala and conservative Tucker Carlson—with the very specific intention, it seemed, to eviscerate it as a detrimental force to political discourse. “He was extraordinarily earnest after the show,” Begala told the New York Times recently. “Really decent. I don’t think it was a show.”

A few months later, Crossfire was canceled.

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