Jon Stewart’s tenure on “The Daily Show” has been nothing short of remarkable. Together with a talented team of writers, corespondents, and various other contributors, the Comedy Central program became something more than just an incredibly funny program — it became a venue for inciting real social and political change.
Over 16 years, Stewart and his team have produced some of the most hilarious, heartfelt, and sobering moments on television. Here are a few of the best.
1. The show comes into its own with “Indecision 2000”
What’s remarkable about the moment that put “The Daily Show with Jon Stewart” on the map is how plain it is. When “The Daily Show” kicked off its now-famous, award-winning “Indecision 2000” election coverage, the show felt a bit different than it does today — while Stewart would grow in confidence to seamlessly weave from news to commentary to comedy, the late-1999 segment that kicked off a full year of “Indecision 2000” coverage still has a late-night talk show cadence of headline-setup-punchline. It’s fascinating to watch Stewart and the “Daily Show” team slowly build the show’s identity from the raw materials presented here.
From this point onward, the show went on to do its best work during election season, and that Stewart is leaving on the cusp of another one is a huge loss.
2. Stewart takes on “Crossfire” and it gets canceled
After making “Crossfire” a frequent target on his show, Stewart took his critique to the next level when he appeared on the show October 15, 2004 — following the release of his book “America: The Book” and one month shy of the 2004 Presidential Elections.
In a soft-spoken, almost meek manner, Stewart proceeded to level brutally frank criticism of the CNN “Left vs. Right” show and its mission:
“Here’s what I wanted to tell you guys: Stop,” Stewart said. “You’re not too rough on [the politicians], you’re part of their strategy. You’re partisan … how do you say it … hacks.”
A few months after Stewart’s appearance, “Crossfire” was canceled, with CNN President Jonathan Klein specifically citing Stewart’s criticisms as one reason. You can watch the “Crossfire” segment below.
3. His post-9/11 opening
Nine days after September 11, 2001, Jon Stewart and “The Daily Show” staff returned to work with a somber opening reflecting on the tragedy that had unfolded just over a week before. “The Daily Show” was just starting to find its footing under Stewart then, but his raw, honest monologue at the start of this episode would be a hallmark of his career.
4. Donald Trump takes Sarah Palin to the wrong pizzeria
While most will remember Stewart’s run on “The Daily Show” for its blend of smart political commentary and laugh-out-loud comedy, Stewart also had no problems with just being full-on hilarious without being too concerned with making any particular point.
Exhibit A: This masterpiece of a segment, where Stewart takes Donald Trump to task for taking then-vice presidential candidate (and Governor of Alaska) Sarah Palin out for “real New York pizza” at Famous Famiglia — a national chain that couldn’t be any further from that.
Stewart’s outrage over this is sublime (and something he revisited when New York Mayor Bill De Blasio was caught eating pizza with a fork and knife).
5. The Malala interview
One of Stewart’s most memorable interviews in recent memory, 16-year-old Palestinian activist and author Malala Yousafzai left the host almost speechless as she spoke about her efforts to fight for equal access to education for women despite the Taliban’s efforts to assassinate her. Yousafzai returned to the show in 2015, on the same day the show addressed the mass shooting at the Emanuel AME Church in Charleston, South Carolina.
6. The CNBC/Mad Money takedown
One of Stewart’s most dogged moments was his week-long targeting of financial news networks in general, and CNBC in particular following the financial collapse in 2008. This culminated in a lengthy, uncomfortable interview with “Mad Money” host Jim Cramer, whom Stewart took to task for being representative of his network’s failings.
It’s uncomfortable to watch — the host has Cramer essentially dead to rights — but it’s a prime example of Jon Stewart dropping his satirical smirk and becoming a full-on crusader, demanding accountability from those who are supposed to hold the powerful accountable.
7. Coverage of the 9/11 first responders’ bill
One of the best things about Jon Stewart’s long tenure on “The Daily Show” was the opportunity it afforded him to follow a story over time, which led to some of his most influential work. One of the biggest stories he took on involved the bill intended to provide a health treatment program for the first responders on September 11, 2001 — many of who were suffering from cancer and other illnesses nine years later.
When the bill was defeated in the House, Stewart heavily criticised politicians who opposed the bill with his trademark wit, but his coverage peaked when Republicans filibustered to prevent the passing of what had become the James L. Zadroga 9/11 Health and Compensation Act — that same day, he dropped the comedy almost entirely to interview a panel of actual 9/11 first responders suffering from various illnesses.
Stewart most recently followed up on the Zadroga Act last month, asking for the names of the Congressmen who opposed the extension of the temporary bill that was eventually passed.
8. The Charleston shooting
There weren’t many times Jon Stewart would cover news so appalling he would completely give up on making jokes. With his last episode about to air, the mass shooting at Emanuel AME church in Charleston, South Carolina, is likely the last time this happened, and Stewart, heartbroken, delivered a monologue on the vicious cycle of gun violence in America, and our national inability to do anything about it.
“Al-Qaeda, all those guys, ISIS … they’re not s— compared to the damage that we can apparently do to ourselves on a regular basis,” Stewart said.
In a way, it’s kind of a fitting note to end this list on, a somber encapsulation of what “The Daily Show” did day in and day out under Jon Stewart, with or without jokes — chronicle the absurdity and tragedy of a nation forever at war with itself.
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