9 Outrageous, Funny and Intense Jon Stewart ‘Daily Show’ Moments (Videos)

After 16 years, the host’s final episode of the Comedy Central satirical news show will air on Aug. 6

Last Updated: August 6, 2015 @ 7:56 AM

Jon Stewart’s long run as host of Comedy Central’s “The Daily Show” comes to an end this week, leaving viewers to reflect on some of his best moments before Trevor Noah takes the helm.

In 16 seasons on the show, Stewart has displayed every side he has, from delivering scathing criticism of cable news, to indignant outrage at the federal government’s handling of Hurricane Katrina, to mournful hope in the days following September 11.

Stewart’s final, extra-long episode of “The Daily Show” is set to air Thursday, Aug. 6 at 11 p.m.

As the comedian prepares to sign off, TheWrap looks back at some of his unforgettable moments as host of “The Daily Show” below:

Indecision 2000
The 2000 presidential election was the first covered by Stewart on “The Daily Show” and it offered no shortage of punchline-worthy moments right up the very end when the Supreme Court ruled George W. Bush the victor. The “Indecision” segment would go on to recur with every subsequent election.

An Emotional Post-9/11 Monologue
As the host of “The Daily Show,” Stewart typically puts a humorous spin on the day’s news, but in his first appearance back on the program after the terrorist attacks of September 11, 2001, he delivered an emotional monologue in place of jokes. “The reason I don’t despair is that this attack happened. It’s not a dream. But the aftermath of it, the recovery, is a dream realized,” he said.

Comparing Hurricane Katrina to Monica Lewinsky
“This is in arguably a failure of leadership from the top of the federal government … Hurricane Katrina is George Bush’s Monica Lewinsky. The only difference is this: hundreds of thousands of people weren’t stranded in Monica Lewinsky’s vagina.”

A Confrontational Jim Cramer Interview
Though Stewart later expressed regret over the interview, admitting that he probably put too much of the blame for the 2008 financial crisis on Cramer, his interview with the host of CNBC’s “Mad Money” stands as one of the most memorable in “Daily Show” history.

Barack Obama becomes first sitting president on “The Daily Show”
When Stewart hosted President Barack Obama on his show for the fourth time in October 2010, it marked the first time a sitting U.S. President appeared on the program. Ahead of the midterm elections, Stewart pressed the president on the progress made in his first two years in office — particularly on healthcare reform, which he characterized as too “timid.”

Backing the James Zadroga 9/11 Health and Compensation Act
When the bill to provide health care to 9/11 first responders was being blocked by Republicans in the Senate, Stewart — in his closest act to actual lobbying — shamed the individual senators and brought on four first responders suffering from health problems. “There are a lot of us who worked on this bill and fought for it daily … But it was Jon Stewart who brought that bill to life,” Representative Carolyn B. Maloney later told the New York Times.

A Long-Running Rivalry With Bill O’Reilly
Each time Fox News host Bill O’Reilly appeared on “The Daily Show,” the audience was in for a fun interview. Though the duo could not be further apart politically, their close friendship always results in a playfully contentious exchange.

Grilling Judith Miller
Stewart has occasionally received criticism for going too easy on the show’s guests, but that wasn’t the case when he grilled the disgraced New York Times reporter Judith Miller, whose false reporting helped take the country into the Iraq War.

Monologue After Charleston church massacre
Jon Stewart’s weariness was evident by the time he announced his imminent departure from the show, and that was perhaps best encapsulated in his monologue after the massacre at Emanuel African Methodist Episcopal Church in Charleston, South Carolina.