Six days after Election Day 2000, the American political climate was in chaos. That night on “The Daily Show” – as had become tradition – Jon Stewart astutely summed things up as the government scrambled to figure out whether George W. Bush or Al Gore would be the next president.

“We’re still in the middle of either a) a constitutional crisis,” Stewart said. “Or b) the funniest sitcom premise since ‘She’s the Sheriff.’”

Such gleeful, alarmed observations were common for Stewart, who in the previous six months transformed from the goofy new host of “The Daily Show” into a leading political pundit. Frustrated with the presidential sideshow and exhausted by “traditional” media coverage? Just tune into Comedy Central (if you could find it, deep into the cable channels) and Stewart would feel your pain.

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“The photo finish that is the 2000 presidential election will ultimately be decided by Florida judges, dimpled chads and accounting skills of part-time municipal employees,” he said that night. “It’s a stunning struggle for democracy centered on a small group of Florida voters; people who may get to determine the next presidential administration, but probably won’t have to live through it.”

Jon Stewart during the later days of "Indecision 2000" (Comedy Central)
Jon Stewart during “Indecision 2000”
(Comedy Central)

But the coverage, titled “Indecision 2000,” wasn’t just about making people laugh so they wouldn’t cry. The success of “Indecision 2000” would guide and inform Stewart’s next 15 years of “The Daily Show,” which in turn helped change political journalism. It was when many Americans concluded that it was not only acceptable but sometimes critical for entertainers to seriously delve into politics.

“For many, Jon Stewart’s perspective was probably the only way to look at the surreal landscape of ‘We can’t determine who won this election,” said Ron Simon, a TV curator for the Paley Center for Media. “But it was also important because it gave the show a voice.”

Un-conventional approach

In the months prior to the election, Stewart, an actor and comedian, was carefully testing the waters of “The Daily Show,” which he inherited from Craig Kilborn in January 1999. While Kilborn was all about the caustic, frat-guy humor, Stewart wanted to go in a different direction of the “fake” news show. For a while, it was a hodgepodge of pop culture and current events as Stewart (who officially steps down from “The Daily Show” on Thursday) attempted to figure out exactly what he wanted the show to be.

“He wasn’t really political – there was no politics in his stand-up routines, to any extent,” said Lisa Rogak, author of “The Angry Optimist: The Life and Times of Jon Stewart.” “I think his first year, he was really focused on the idea: ‘How do we convey this fake news program?’ Once the convention and presidential primary and campaign season took over, maybe that gave him a bit more permission to cover politics.”

[Can we go on without Jon Stewart? Of course we can. He’s shown us how.]

It was all the ammunition the show needed: Stewart and his team went full-steam ahead with the 2000 election season. He sent an all-star roster of correspondents (Stephen Colbert, Steve Carell, Mo Rocca, Nancy Walls, Vance DeGeneres, etc.) to both conventions.

At the Republican gathering in Philadelphia, Carell reported on Bush’s education initiatives: “When he became governor, Texas schools ranked in the bottom 15 percent nationally. Today, they are in the bottom 20 percent. Jon, that is a dramatic 5 percent decrease in sucking.”

Steve Carell at the 2000 Republican National Convention. (screengrab via Comedy Central)

Meanwhile, Rocca gave his dispatch from the Democratic convention in Los Angeles. “Last night’s theme was represented by the slogan ‘You ain’t seen nothing yet,’” Rocca said. “And Jon, the Democrats have really delivered on that promise. I’ve been here three days, and indeed, I ain’t seen nothing.”

The show continued to hit its stride and was a well-oiled machine by the time November rolled around: Stewart and his correspondents, along with co-creators Lizz Winstead and Madeleine Smithberg and executive producer Ben Karlin, had found the perfect voice for their coverage. The mainstream media took notice of the small basic cable show that was satirizing every aspect of the election (even those hanging chads).

As the news media exhaustively covered the story, Stewart joined in — but, to the relief of many, emphasized the absurdity. From the electoral rules (“After 19 days of endless court battles, the Florida vote has been certified . . . giving the state and the presidency to George W. Bush by a total of 537 votes. Wow, that’s a landslide if you’re running for student council treasurer.”); to CNN changing its mind four times about who actually won Florida; to theorizing that the people of Florida liked the “No more Gore” chant simply because it rhymed.

Through the jokes, Stewart proved he was also a sharp commentator who could cut through the noise; soon, programs like the “Today” show sought him out as a pundit. “His emergence at that period was just the perfect antidote to the insanity absorbing American politics,” Simon said.

In a move that Stewart found amusing, he was deemed “prophetic” because of the “Indecision” title – a name that had actually been in use on Comedy Central since Al Franken specials that aired in 1992. Now, the moniker was frighteningly literal.

“It’s been the craziest election any of us can remember. Calling this whole thing ‘Indecision 2000’ was at first a bit of a lighthearted jab, perhaps at an attempt at humor,” Stewart said on his show that November, smoking cigarettes and wild-eyed from lack of sleep. “We thought we were kidding, quite frankly.”

Stephen Colbert on “The Daily Show” in 2000. (screengrab via Comedy Central)

During one episode, Colbert was on the verge of tears because he just wanted to go home and see his family – but he was trapped at the election desk, waiting for the results.

Serious comedy

Eventually, about a month after Election Day, the court-approved results were in. “It is now official, we can call it – at 855 hours and two minutes of this election night, the state of Florida and its 25 electoral votes…will go to George W. Bush,” Stewart said as the audience half-cheered and booed. “And the crowd loves it!”

Soon after, the accolades started to roll in, as Stewart wound up on critics’ “best TV of the year” lists in December.

“No one in late-night TV comedy distinguished themselves more than Stewart and company, who brilliantly savaged not only the news but the news media nightly with uncanny accuracy and zeal,” wrote Phil Rosenthal of the Chicago Sun-Times. “The biggest disappointment in finally resolving the race for the White House is that it ends months of smart, on-target and laugh-out-loud satire of a campaign.”

[Many millennials are about to lose their most-trusted news source: Jon Stewart]

He was also credited for keeping younger viewers interested in politics. According to a Pew Research Center poll at the time, an impressive 47 percent of 18-to-29-year-olds turned to late-night TV for the majority of their election news. By the time “The Daily Show” launched “Indecision 2004,” a Rolling Stone cover story deemed Stewart “the most trusted name in news.”

The show’s legitimacy was cemented early on when it was awarded the prestigious Peabody Award in 2000 and 2004 for its “Indecision” coverage. Jeffrey P. Jones, director of the Peabody Awards at the University of Georgia, said that by giving the award to Stewart, it was validation that comedians could have an important role – even when journalists and pundits are uncomfortable when entertainers show up in the public information space.

However, he said, Stewart’s “Indecision” coverage was a valuable lesson. “It was the moment in which American culture realized that entertainment journalism can actually play a real, productive role in citizenship,” Jones said. “And not just frivolous, throwaway humor.”

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