Back in 1999, I'm pretty sure, no one could have predicted that replacing a smug, fratboy wiseass with a C-list stand-up comedian on a sparsely watched late-night basic cable comedy show would lead to a sea change in America's media landscape. It's kind of redundant now, as we bid adieu to Jon Stewart's 16-plus-year tenure on The Daily Show, even to bring it up. But for better or worse, Stewart has become our go-to news figure. The guy who endlessly (and increasingly ineffectively) referred to himself as "just a comedian" ended up my generation's Walter Cronkite.
Sure, he may lack the gravitas of old Walt (maybe a mustache would have helped), but as nightly news broadcasts continued their plummet into irrelevance, newspapers shuttered their local bureaus and cable news outlets shrugged off even the most laughable stabs at "objectivity" in favor of veering headlong toward their respective bases, Stewart and crew emerged as the only voice calling out all sides on their bullshit.
There's a bit of "who made who" going on as well. How much of Stewart's early skewering of "fair and balanced" or CNN's reliance on gimmicky scoopage is responsible for their current sad states? Perhaps the relationship was more symbiotic, with both TDS and (especially) Fox News feeding off each other and gaining strength through the galvanization of their respective factions. Which came first? Who killed the world?
And for all his rightful mocking of a certain cable news organization (rhymes with "Lox Booze"), would Stewart have risen to prominence without George W. Bush and that administration's subsequent missteps? I'm certain an Al Gore presidency would have offered its own targets, but would they have been as fat and slow-moving as Dick Cheney shooting a guy in the face, or the Iraq War debacle (a.k.a. "Mess-O-Potamia")?
Stewart signs off for the last time tonight, and I won't lie: Between his departure and that of Colbert and Letterman in the same year, I don't really feel the need to watch late-night again. Larry Wilmore has been adequate stepping into the Report's time slot, and we'll probably give Trevor Noah a shot. Maybe. And yeah, Colbert will be back later this year, but you and I know it won't be the same. For while he'll surely be better than Jimmy Fallon or James Corden (how can he not?), it really is the end of an era.
At least we'll have one more late-night host without the given name of "James."
Nothing that happened Saturday, no sign warning "God hates HMOs," no pithy rejoinder from Stewart, is going to stop the Republicans from taking back the House this week. And the GOP has not demonstrated, at any time in the last 18 years, any interest in compromise or reconciliation. Stewart's "merging traffic" analogy at the end of the day was flawed, because the opposition doesn't want to wave you in as the lanes narrow, they want to run you off the road and laugh as your car bursts into flames.Nailed it.
All good things, and all that. Stewart takes the chair one last time tonight, and though it won't be any consolation to those who can't BELIEVE he's bailing on the show just when shit's getting good, maybe these Daily Show moments (minus one we just saw this week) will help us go gently into that good [late] night.
Headlines - Indecision 2000 - Victory: Bush
Up to the 2000 election, Stewart largely contented himself with interviewing entertainers and authors, to often snooze-worthy results. The election of George W. Bush, however, would be the crucible that formed what The Daily Show would become (to coin a phrase). The show immediately following the Supreme Court's decision in Bush v. Gore gave some pretty strong hints as to what was to come.
First Show After 9/11 - September 20, 2001
Halting, awkward and painful to watch at many points. Ranging from ruminations on the assassination of Martin Luther King Jr. to an ultimately depressing assertion that "light" and democracy would somehow win. This was really the point where The Daily Show finally determined its direction. "Our show has changed. What it's become, I don't know."
"Cheney's Got A Gun" - February 13, 2006
There's a lot to unpack here, as they say: "getting out of a car" to walk the covey of quail (to say nothing of the ludicrousness of the Armstrong Ranch hunt to begin with), Cheney's perfunctory visit to the victim, Stewart's outright glee when talking about it. But while his monologue is fun enough, Ed Helms's "re-enactment" and Rob Corddry's commentary are excellent as well.
Crossfire Appearance - October 15, 2004
How many times can you say your appearance on a show led to that show's cancelation (let's leave Ted McGinley out of this)? Stewart appeared on the CNN "debate" show in October, 2004, and it was canceled three months later. This was also possibly the first instance of the "journalism versus comedian" discussion that would follow Stewart for the rest of his tenure.
Jim Cramer Interview - March 12, 2009
Was Stewart being too much of a bully when he broadsided Mad Money host Cramer in the wake of the 2008 financial crisis? Probably...? The interview, recall, was the culmination of a roughly week-long back and forth between Stewart and CNBC/Cramer about the financial networks' hilariously appalling inability to see the looming disaster. Cramer was obviously unprepared, and the entire segment can be viewed as a microcosm of the wider public's outrage at Wall Street's excesses.
"Conservative Libertarian" - March 18, 2010
"And in my America, nobody tells people when they can masturbate."
9/11 First Responders React to the Senate Filibuster - December 16, 2010
I think we can all agree Stewart is at his best when pissed off, and whatever your views about his politics, everyone can get behind his continued efforts to push for the passage of the 9/11 first responders' compensation bill. This was also the only time a Cecil Turtle impression was not appropriate for a Mitch McConnell appearance.
Chaos On Bullshit Mountain - September 19, 2012
Pointing out the inaccuracies and outright falsehoods excreted out by Fox News is old hat now, but Stewart perfected it, and it rarely gets better than here, where he takes down Fox's analysis of Mitt Romney's "entitlement society" comments.
The Eric Garner Grand Jury Decision - December 3, 2014
"I honestly don't know what to say. If comedy is tragedy plus time, I need more fucking time." Stewart announced his retirement from TDS on February 10 of this year, two months after the Garner decision, which — after watching this again — I'm still pretty confident had a lot to do with it.
War on Christmas - Shit's Getting Weird Edition - December 12, 2013
The imaginary assault on Jesus' birthday has been a favorite topic of The Daily Show for more than a decade, and any one of those segments is eminently watchable, but my favorite might be Gretchen Carlson's freaking out over a Festivus pole.
The Curious Case of Flight 370 - March 24, 2014
Fox News received the brunt of Stewart's vitriol because it's the barn door in the whole shooting gallery of cable news idiocy, but we tend to forget he was just as liable to go after CNN, the 24-hour news cycle itself (take special note of Don Lemon's "black hole" stupidity), and the awesome ouroboros resulting from CNN and Fox's respective coverages.