My 10 favorite Jon Stewart moments from his Daily Show tenure

In 1999, Craig Kilborn left The Daily Show, taking my beloved ‘5 questions’ with him, and Jon Stewart’s Daily Show experiment began.

Tonight Jon Stewart concludes that experiment — a sixteen year sketch in which he plays the sane man in the insane asylum that is American politics. Somewhere along the way his work became essential viewing.

Stewart filled the void left by ‘5 questions’ with a Murderer’s Row of hyper-talented correspondents — Colbert, Carell, Helms, Corddry, Bee, Jones, Wilmore, Mandvi, Black, Cenac, Schall, Riggle -whom would all go on to alter the comedic landscape in their own ways. But it was his own moral grounding and insightful invective that helped steer myself and many others through the turbulent aughts and beyond.

I have watched every episode of Stewart’s tenure. It may sound absurd but it happened quite casually. I can’t imagine not having watched every episode. 11pm was a necessary escape for me while bemoaning the state of affairs in March of ’03 or September of ’05 and it continued to be a respite, albeit an earlier in the day-one, when I entered the workforce and made viewing the previous night’s installment a staple of my lunchtime regimen. In 2010 I was in DC for the Rally. You get it.

That being said these are ten of my favorite moments. None include correspondents because this week is all about “Jonny Beef Stew.”

10. 9/20/01

In his first show after 9/11, Stewart grabbed a baton from Edward R. Murrow and ascended to the difficult role of moral arbiter in a scary and confusing time. As with airport security, there is the pre- and post-Daily Show 9/11 world. He was always more Carlin than Kronkite but the attacks changed Stewart and his moral compass became many of ours in the aftermath.

9. Debating O’Reilly — Part 3

Part of a multi-game, home and away series that witnessed O’Reilly and Stewart spar on each other’s shows multiple times in the span of weeks. You could effectively argue for many other Stewart v. O’Reilly matches including recent discussions about Common and/or white privilege, but this one features Stewart doing his finest breakdown of the Fox faux-outrage machine, and he does it on their field. It was always a pleasure to watch these guys go at it because they are both exceptional at their craft but Stewart bests O’Reilly time and again. It’s worth watching their full unedited discussion but jump to part 3 for the good stuff. That whole Fox News v. Daily Show discussion? Forget it. You can watch the 12th round above.

8. Bush v. Bush

April 28, 2003

This clip may view like a simple lesson about hypocrisy or why you shouldn’t trust politicians but I wish I could emphasize how revolutionary this segment felt when it aired. To truly appreciate it you need to appreciate the passions ignited during ’03, the fact that war critics were shamed as traitors and weaklings, and the fact that the Daily Show’s rapid fire brand of cutting footage to expose hypocrisy was still so fresh — YouTube and Facebook wouldn’t arrive for another two years.

When even the slightest war dissent was getting steamrolled Stewart used Bush’s own words to damn his argument. This is next level rhetorical maneuvering.

7. “If you don’t stick to your values when they’re being tested, they’re not values, they’re hobbies.”

January 22, 2009

This segment contains one of Stewart’s oft-quoted (and best) lines. But it’s even more prescient because it documented the what would become historic Republican obstructionism at its genesis. Consider that in the wake of the largest financial crisis in a generation Republicans claimed their only legislative goal was to make Obama a one term president. Also consider that in the face of that obstructionism the economy still recovered under Obama’s leadership, he passed health care reform, never came to take anyone’s guns, got Bin Laden, and was reelected and this clip is even wilder in retrospect. Watch how talking points for a generation unfold during the 2nd day of the Obama presidency and learn that they were divorced from reality from the start.

6. The final speech from the Rally to Restore Sanity

October 30, 2010 on the Washington Mall

Because “sometimes the light at the end of the tunnel isn’t the promised land. Sometimes it’s just New Jersey.” Using the analogy of the “you go, I go” approach that cars take when entering the Holland Tunnel, Stewart notes that Americans work together everyday and that our differences are never as extreme as cable news would have you believe. In his own words:

Every one of the cars that you see is filled with individuals of strong belief and principles they hold dear — often principles and beliefs in direct opposition to their fellow travelers.

And yet these millions of cars must somehow find a way to squeeze one by one into a mile long 30 foot wide tunnel carved underneath a mighty river. Carved, by the way, by people who I’m sure had their differences. And they do it. Concession by concession. You go. Then I’ll go. You go. Then I’ll go. You go then I’ll go. Oh my God, is that an NRA sticker on your car? Is that an Obama sticker on your car? Well, that’s okay — you go and then I’ll go.”

5. The Saga of Jim Cramer

March 4, 2009

It’s no secret that Stewart pummeled Cramer but it’s important to remember how the saga began. After a rant by CNBC’s Rick Santelli blaming homeowners for the subprime mortgage meltdown went viral, Stewart ripped Santelli’s “cheap populism” noting that Santelli, a former derivatives trader on Wall Street, was using his outburst to distract from the fact that Wall Street had devastated the global economy through the creation and insurance of collateralized debt obligations and then went on to accept $2 trillion in taypayer money: “Wall Street is mad as hell and they’re not gonna take it anymore — unless “it” is $2 trillion in bailout money,” Stewart quipped.

After maligning Santelli, Stewart then ran a package of clips featuring CNBC hosts recommending the purchase of a bevy of stocks that would ultimately collapse — Bear Stearns and Lehman Brothers included. He follows this up with a package featuring CNBC hosts lobbing softballs at Wall Street CEOs, ending with a clip of a CNBC host guffawing along with with a billionaire who would later go to prison for running a Ponzi scheme.

Jim Cramer took umbrage with this portrayal and responded to Stewart on CNBC. This was a mistake. In the clip below, about three minutes in, Stewart takes Cramer to task, and as with Bush, uses Cramer’s own words to damn him. A few days later Cramer would appear on Stewart’s show attempting to schmooze his way out of it. The result is a lesson in how journalists should be interviewing those who make excuses for their damage: through preparation, understanding of the subject matter, and deflection of schmoozing. Stewart’s dismantling of Cramer and the institutions he represents was the closest thing to catharsis many of us had in the wake of the financial crisis. Though John Oliver’s foreclosure piece helped too.

March 9, 2009
March 14, 2009 — Cramer Interview part 1
Cramer Interview part 2
Cramer Interview part 3

4. 365 days later

May 3, 2004

Stewart didn’t let the country forget the war and didn’t let us forget the consequences. Arguably his funniest over-the-top Woody Allen impression comes via him doing Woody Allen doing Paul Wolfowitz. And after a nerve-rattling recap of the year that followed Bush’s “Mission Accomplished” spectacle Stewart refocuses the consequences once again after a return from commercial break:

He rips the conservative leaning Sinclair Broadcasting Group for banning its ABC affiliates from broadcasting a reading of the names of the then 700 dead American servicemen and women in Iraq. “Sinclair prefers their politics disguised as money,” Stewart opined. More than 4,000 servicemen and women lost their lives in the Iraq War in the years following the Mission Accomplished event.

3. Cold opening into a satire of Glenn Beck’s sophism

March 18, 2010

Because sophism is easy. Because if you’re preconditioned to look for connections, and they aren’t there- you’ll still find them. Long before Glenn Beck expressed regret for ‘helping tear the country apart’, Stewart answered the Beck insanity with a cold open that featured his greatest piece of acting and which elevated the bar for political satire to new levels.

2. Crossfire

October 15, 2004

You knew this one was going to be here. It’s become trite to reference this clip but again, you have to appreciate the impact of it when it actually happened. Stewart’s dress-down of Carlson et. al. did little to change the hyperbolic cable news landscape but it did get Crossfire cancelled, which is still something. It was also the moment when his detractors learned he wasn’t “their monkey.” Bill O’Reilly has fairly pointed out that it’s disingenuous for Stewart to downplay his impact and stress that he’s just a comedian. But before this appearance a lot of those same detractors were using that same argument — “he’s just a comedian” — to downplay his most effective arguments. Watch above to see how that approach worked out for Tucker Carlson.

  1. The Zadroga Act and 9/11 first responders
December 13, 2010
With 9/11 first responders on December 16, 2010.

This was Stewart’s finest hour. After Republicans blocked passage of a bill to provide health care to 9/11 first responders, Stewart launched into the most powerful tirade in the show’s history (roughly 2 minutes into that first clip). He juxtaposes Republican exploitation of 9/11 for political gain with those same Republicans voting against health care for 9/11 first responders whilst “I’m Proud to Be an American” plays in the background. The result is devastating.

Some background: Up until that moment, Congressional Republicans had been proudly proclaiming they would block any legislation put forth until the reauthorization of the Bush tax cuts — tax cuts whose expiration date they’d set. Enter the James L. Zadroga Health & Compensation Act, a bill without any controversial riders that sought to provide healthcare to first responders who were made ill by their work at Ground Zero. Sickeningly, the bill got caught up in the Bush tax cut extortion and failed to make it through Congress (that’s the Zadroga Act that the (R)’s are voting against at the end of the first clip).

That first clip could have been the end of Stewart’s Zadroga coverage but he instead taught us all a lesson in what it means to “never forget,” by bringing ailing first responders on to his next episode to discuss their plight and their feeling of abandonment (the second clip).

It wasn’t until after Stewart gathered those first responders for a roundtable discussion that acted as a “have you no decency?” moment for Congressional Republicans, that the likes of Guiliani and Co. shamed their party into doing the right thing and passing the bill. Both the first responders involved and politicians from both sides of the aisle credited Stewart with getting the bill passed.

Never forget that no matter what excuses were later peddled — concerns about the cost of the bill or how it would be distributed — that (R)’s blocked that bill simply to extort tax breaks for those who have benefited the most from this country already. Never forget that without Stewart they might’ve gotten away with it. But more importantly, never forget those first responders. Thanks Jon.

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