‘The Daily Show’: Jon Stewart’s 10 Best & Most Unforgettable Moments 

When Jon Stewart took over the “Daily Show” desk in 1999, no one predicted Comedy Central’s late-night satire would become a pop culture cornerstone to help shape and define politics in a post-millennial America.

Now, after 16 seasons, the iconic host is saying goodbye.

The legacy Stewart leaves behind as a voice of a generation is considered irreplaceable by many, and fans will continue mourning his loss long after the comedian’s final show on Thursday night.

Through laughter, tears, confusion and anger, Stewart’s unabashed criticism and analysis of current events often bridged the gap between silly and searing. Viewers appreciated his unforgiving honesty during the country’s most harrowing ordeals, and were even more thankful for someone to pinpoint the humor within our most embarrassing ones.

Although Stewart was welcomed into millions of households over the years, he told audiences there’s just one he intends to focus on from this point forward.

“I’m gonna have dinner. On a school night. With my family,” the host said on air, after news of his retirement broke. “Who I’ve heard, from multiple sources, are lovely people.”

Now, in honor of Stewart’s sign-off, Access Hollywood counts down 10 of the most memorable moments from “The Daily Show with Jon Stewart”:

Indecision 2000

The mangled presidential election between Al Gore and George W. Bush was the perfect setup for newly-minted “news” anchor Stewart, as he began to find his “Daily Show” groove. He narrated the now-historical drama with the same sarcastic incredulity many viewers were feeling, and it helped set a trademark tone and style adopted — and eventually beloved — for many years to come.

Post-9/11 Monologue

Less than a year after President Bush took office, the most devastating terrorist attack in American history left our nation reeling. A proud New Yorker, Stewart’s most emotional “Daily Show” appearance to date cemented his status as a TV icon. Nearly 14 years later, Stewart’s grief still lingers – as does ours.

Unforgettable Correspondents

Stewart isn’t the only comedy icon whose career “The Daily Show” launched. Stephen Colbert, Steve Carell, Ed Helms and John Oliver went on to become bona fide stars in their own right, and fan favorites Samantha Bee, Jason Jones, Jessica Williams and Kristen Schaal, among others, have all been catapulted to the next level thanks to their indelible contributions to the “Daily Show” brand. Longtime correspondents received deserving accolades upon their own farewells, and none were so appropriately wacky and lovable as the one for 10-year “Daily Show” veteran Bee. Let’s see Stewart top this.

Bill O’Reilly: Friend Or Foe?

Is the longtime Fox News pundit and bestselling author the brash, stubborn yin to Stewart’s whimsical, acerbic yang? Or is Bill O’Reilly simply the “Daily Show” antithesis? Regardless of their different political views, the two hosts engaged in on-air banter a number of times throughout Stewart’s tenure. Some back-and-forths got more heated than others, but each man’s willingness to at least acknowledge the other’s point of view made for some of the liveliest and even most respectful discussions in “Daily Show” history.

“War On Christmas”

Bill O’Reilly is but one aspect of Fox News that “The Daily Show” loved to skewer. One of Stewart’s most memorably eviscerating segments targeted the cable network’s purported “war” on Christmas. Updated annually, this is one of many “Daily Show” packages viewers unwrapped with glee year after year. Kind of like a kid on…well, you know.

READ: Debut Of ‘The Daily Show With Trevor Noah’ Set For Late September

Jim Cramer Interview

Stewart’s skill as an interviewer was obvious from the start, and his technique only continued to develop alongside the show. While many guests made for affable onscreen counterparts, Stewart was often brutally combative with those whom he felt represented society’s most egregious calamities. When CNBC host and financial analyst Jim Cramer appeared on the show in the wake of 2008’s economic collapse, Stewart let it rip. Some perceived the takedown as a cheap shot, but many others hailed Stewart’s journalistic sensibility. For someone who never wanted to be considered a traditional “newsman,” Stewart often did the business proud.

“Gitmo’s World”

Despite his generally left-leaning ideology, Stewart had no problem pointing out flaws in the government’s most prominent Democrats – including President Obama. One of the president’s oft-quoted campaign promises was to close the prison at Cuba’s Guantanamo Bay within his first year in office, a vision that’s been left unrealized as he nears the end of his second term. “The Daily Show” chronicled the horrors of Gitmo life in a series of goofy riffs, including “Guantanamo Baywatch,” but it was the Sesame Street satire “Gitmo’s World – Death to America” that illustrated the program at its most bitingly absurd. When a message is this disturbing, perhaps only Elmo should deliver it.

Malala Yousafzai Interview

Stewart welcomed the teenage activist to “The Daily Show” in 2013 to promote her bestselling memoir. What many viewers didn’t know was that Malala wasn’t just any advocate. The year prior, she was hunted down and shot in the head by Taliban terrorists who had overrun her Pakistani community and banned girls from attending school. Malala was targeted because of her public support for women’s education. She survived her injuries and went on to become the youngest recipient of the Nobel Prize, and continues to inspire a global audience. Stewart isn’t often star-struck, but we’ll give him a pass on this one.

Missing Malaysian Airliner

When a Malaysian commercial airliner went missing mid-flight in 2014, it ignited one of the most mysterious tragedies in aviation history. What nearly baffled Stewart more was the news coverage of the incident, particularly CNN’s. “The Daily Show” takes pride in its “fake news” reputation, and is never better than when poking fun at real news that has to be seen to be believed.

Donald Trump Runs For President

The Donald’s trainwreck of public appearances since announcing his presidential bid is matched only by his leading poll numbers. “Daily Show” fans are already bemoaning Stewart’s absence in anticipation of what the real estate mogul will do next on the campaign trail. Stewart said upon his retirement announcement that he couldn’t fathom covering another election, but we swear we can see a twinkle of regret in his eye at the downright rotten timing his departure turned out to be. 

–– Erin Biglow