Four nights a week, we tuned in to The Daily Show to process the previous day’s events, watch Jon Stewart banter with authors and actors, and — if we were really lucky — see him rip into Fox News like a rabid terrier. (We’ll miss you most of all, clip-montages-of-contradictions-while-Stewart-offered-scolding-commentary.) But there were a handful of times over his 16 years behind the desk when the host did more than just crack us up or remind us that “Santorum” has slowly transformed into a slang term for something unspeakable. (Google it, but don’t say we didn’t warn you.)

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These were the moments when he’d press a guest to explain why something had fallen short of expectations, or called folks out when he felt that citizens were being purposefully misled by misinformation, or dug into a story with a depth and sense of outraged humanity that the usual news sources hadn’t been able to tap. Stewart constantly told people that he was not a journalist, he was a comedian — yet there were times when he not only displayed impressive reporting/interviewing chops or got to the heart of a tragedy like 9/11 or Charleston that you felt he’d beaten the Fourth Estate at its own game. Here are 10 examples of when Stewart outdid journalism — those incredible instances when he turned The Daily Show into something much more than a late-night comedy staple.

10. Indecision 2000

Remember the WTF shitstorm of the 2000 Presidential election? The Nader scapegoating, the hanging chads, that damned recount? Daily Show correspondent Stephen Colbert compared it to the JFK vs. Nixon election of 1960; when Stewart asked if that meant one of the candidates would lead us back to Camelot, the reporter corrected him. “I’m getting more of a ‘Nam vibe…you know, unwinnable wars, inescable downward spiral, chaos in the streets. That sort of thing.” While the rest of the media spun itself out of control, Stewart and the TDS crew proved they could cut through the white-noise chatter and channel the did-we-just-get-screwed-here vibe that a lot of people felt. It was the first time the show proved it was capable being a satirical juggernaut and could beat the mainstream pundits at their own game. Not for nothing did this months-long coverage net them a Peabody. DF

9. The War Against the Poor

The chasm between the have and have-nots in 2011 was continuing to widen when Warren Buffett, of all folks, suggested that billionaires were not being taxed enough — and some acted as if it was the equivalent to suggesting a hostile socialist takeover. Besides, why go after the “productive class” when the lazy, shiftless poor were the ones really responsible for our income inequality? Enter Stewart, who in his “World of Class Warfare” segment, went after those who kept gunning for the financially strapped. The host started by comparing the blasé response to Obama’s “drop-in-the-bucket” proposed tax revenue to the conservative outrage over the lower price tags on keeping the NEA and NPR going. He then went after those who suggested that a family of four who made slightly over $22,000 a year would be fine, because according to Fox News, they live extravagant lives, i.e. many own a refrigerator. Few in the media were calling out those who’d divide society into “the makers and the takers” with such bite and bile. DF

8. Addressing 9/11

Stewart goal when he addressed his audience nine days after the attacks on 9/11/01, after most anchors and analysts have had their say, wasn’t to best his peers in the media: “It’s another entertainment show beginning with an overwrought speech of a shaken host. And television is nothing if not redundant.” Rather, he was just trying to get through the eight minutes of his opening monologue without breaking into tears, which he barely managed to do. Stewart lauds the humanity he already sees in the rebuilding effort while damning the “chaos” of those that perpetrated the violence. It’s mournful and hopeful, not at all funny, and stood as a example to follow at a time New Yorkers and Americans in general felt understandably lost. After noting that he could see the World Trade Center from his house, he concluded, “You know what the view is now? The Statue of Liberty. The view from the south of Manhattan is now the Statue of Liberty. You can’t beat that.” ML

7. First-Responder Care

Having covered politicians exploiting the events of September 11th for years, Stewart was rightfully enraged by Congress’ slow adoption of the James L. Zadroga 9/11 Health & Compensation Act, which would provide healthcare to first responders who developed cancer and other diseases as a result of their heroism. His anger reached its peak on December 16, 2010, when he brought on seriously ill members of the NYPD and fire departments who had served on 9/11, showing his audience that the bill, which had been stalled by a Senate Republican filibuster, had real-world consequences for those who were suffering. Six days later, the bill finally passed, signed into law shortly thereafter by Obama, who credited The Daily Show for applying the necessary political pressure. “I don’t even know if there was a deal, to be honest with you, before his show,” Kenny Specht, whom Stewart had on the broadcast, later told the New York Times. “I’ll forever be indebted to Jon because of what he did.” TG

6. Indecision 2004

American presidential elections prove the juiciest and most rewarding stretches of time for TDS, and in 2004, Stewart and his team matched their pitch perfectly with Howard Dean’s yelps and Zell Miller’s rants. The foibles and the fuck-ups were highlights, sure, but after 9/11 and George W. Bush’s Iraq War, Stewart was keen to peer at the appeals candidates used to push voters’ buttons that cable networks glossed over. Beginning with the Republican and Democratic National Conventions, Stewart zoomed in on the Bush team’s fearmongering, Kerry’s wooden appeals to the disenchanted, and the ultimately painful similarities between the two. With correspondents Stephen Colbert and Steve Carell still on board and the rest of the Best F#@king News Team Ever in rare form, there’s a reason the show won another Peabody for its Indecision coverage. ML

5. CNN’s Boston Bomber Coverage

As Stewart dedicated more and more time excoriating the media itself, he usually focused his ire at the folks on “Bullshit Mountain”; his second favorite cable target, however, was CNN. He roundly, rightfully spanked the network for its alternately empty reportage and irresponsible speculation of the aftermath of the Boston Marathon bombing in 2013. CNN first announces on-air that a suspect has been taken into custody before retracting this claim an hour later; as the network “debat[es] the merits of its own fiction,” the Daily Show host dubs the network “The Human Centipede of News.” Later, as the dragnet closes in on Dzhokar Tsarnaev, Stewart mocks the channel’s inability to fill the gaping maw created by the 24-hour news cycle — e.g. empty-handed reporters take to describing barking canines that “might be smelling what we smelled.” When a segment in September 2013 finds that CNN’s unsavory tactics in Boston earned them a record number of viewers, Stewart offers this sound advice: “We’re in an abusive relationship with CNN. It’s time we kicked those bastards to the curb because we have to remember, this network was created by Ted Turner — not Ike Turner.”

4. Grilling Nancy Pelosi

It’s a mistake to say that The Daily Show only went after the right. Exhibit A: Democratic congresswoman Nancy Pelosi’s grilling on January 30, 2014, when the host pressed her on why those on the left sanctimoniously decried the corrupting influence of money in politics while still taking loads of lobbyist money. (A flustered but clueless Pelosi responded at one point, “I never could understand — and I should — why the public paints us with the same brush as the Republicans when it comes to special-interest money in Washington, D.C.”) The extended interview is a terrific moment of Stewart giving some much-needed tough love to the Democrats, hammering the politician on the Administration’s failure both to implement the Affordable Care Act smoothly and to position the party as the sane, intelligent alternative to their partisan counterparts. “The things that you’re in control of? Make them work,” Steward instructed her sternly. “[The GOP has] so embarrassed themselves with their knuckleheads that the Democrats have an opportunity to establish themselves with much more authority than ever before.” Pelosi agreed, but Stewart’s reaction suggested he wasn’t sure she really heard him. TG

3. Kathleen Sebelius on Obamacare

When U.S. Health and Human Services Secretary Kathleen Sebelius appeared on The Daily Show October 7, 2013, her job was to do damage control: The recent roll-out of the Obamacare website had been a glitch-y disaster, and it was critical that she assure Stewart’s young audience that the Administration knew what it was doing. Instead, she bombed, awkwardly oscillating between patronizing laughter and vague, unhelpful answers in the face of Jon’s objections to the Democratic leadership’s organizational incompetence and deeply flawed healthcare reform. “It’s better today than it was yesterday, and it will keep getting better,” Sebelius spouted near the end, her cheery words sounding like such an unconvincingly hollow sound bite. Stewart couldn’t even mask his smirking doubt: “I hope things work out,” he told her. It didn’t for Sebelius: Six months later, she resigned. TG

2. The Judith Miller Interview

When Stewart brought on former New York Times journalist Judith Miller earlier this year, he clearly knew what he felt about her role in the Iraq War, which he calls, “the most devastating mistake in foreign policy that we’ve made in 100 years.” For an extended 22 minutes, he attacked the influential stories Miller produced in the days and months leading to the preemptive military action — her inaccurate sources, her lazy reporting and most importantly her interest in pushing a narrative about Saddam Hussein acquiring nuclear weapons. One particularly telling moment finds the former journalist justifying her actions with a fear she insists everyone should have felt; Stewart replies, “A reporter’s job is not to be frightened.” Though Miller budges not an inch, and Stewart confesses to feeling “incredibly sad” about the “institutional failure” the fiasco indicates, this segment once again drew attention to how a member of the Fourth Estate became a cog in the war machine. ML

1. Charleston

“I have one pretty simple job,” Stewart said at the top of his program on June 18th, 2015. “I look at the news and I write jokes about it…I didn’t do my job today.” The reason, he claimed, was that the mass shooting that had happened in Charleston, South Carolina, the evening before hadn’t really left him in a go-make-the-funny mood. So instead, the host spoke about our society’s inability to neither heal nor even acknowledge “the gaping racial wound” that still plagues out country. He spoke of the disparity between dealing with threats from outside and threats in our own backyard. “We invaded two countries,” he said, visibly exasperated, to keep Americans safe, but we can’t seem to protect nine people in a church. There were a number of what-does-it-all-mean op-ed pieces that ran in the days after the tragedy; Stewart’s direct address to his viewers instead asked why a country seems so “steeped in this culture” of hate refuses to recognize it. As with his 9/11 address, he seemed to be working something out in public — but still managed to get at the heart of the matter in a way that precious few had. DF

originally posted on rollingstone.com

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