On January 11, 1999, Jon Stewart sat in the host chair of The Daily Show for the very first time, addressing a skeptical audience about the change in the building. “I know I can never be your real father,” he said. “But I don’t want to be. I just want to sleep with your mother. My god, the woman is insatiable!”
And with that quip, Stewart kicked off a staggering ongoing run: He's gone from being mom’s boyfriend to an American king. He’s universally beloved in the worlds of both comedy and politics, with 18 Emmys to show for it. When he gets back in the chair after a summer-long absence on September 3, he’ll return as a legend.
But even though so much has changed in the 14 years since his debut, it’s remarkable that even his first show was dynamic, shrewd, and damn funny. Through wisecracks about Monica Lewinsky and Strom Thurmond, Stewart eased into his hosting role and gave a brilliant teaser into what The Daily Show would become.
“Welcome to The Daily Show. Craig Kilborn is on assignment in Kuala Lumpur, I’m Jon Stewart,” were Stewart’s first words on Comedy Central cameras. The hosting switch was by no means a peaceful affair: The former ESPN anchor Kilborn had gotten himself into trouble by making inappropriate sexual jokes about the Daily Show's head writer in Esquire magazine, and soon bolted to The Late Late Show on CBS. And so a visibly nervous Stewart sat in Kilborn’s chair in early January of 1999, determined to make a name for himself after a stint at MTV’s miserably rated The Jon Stewart Show.
Stewart immediately displayed the wit and self-deprecation he’s become so famous for. “Since we were busy during the holidays lowering the desk, here’s some stuff we missed,” he says (he’s listed at 5’6”). His segment titles are just as punny as ever (“The Last Blow” for the Lewinsky trial, “Nothing But Net…Profits” for the NBA lockout), and he lampoons his targets, like Thurmond, with wicked deftness.
Perhaps most impressively, Stewart shows off his soon-to-be legendary interviewing chops with actor Michael J. Fox. The two establish an easy rapport right away: They challenge each other to a fight, banter about Heidi Klum and Titanic, and throw the word “hanky-panky” around a couple times. Just from this interview, it’s pretty clear why The Daily Show would become the hot spot for presidents, musicians, and astrophysicists alike.
Of course, it wouldn’t be The Daily Show without hard-hitting correspondents, and a young Stephen Colbert checks in to smear the commercialization of Clinton’s trial. However, it seems that he hasn’t quite yet developed the far-right persona he would on The Colbert Show: “The Republicans are being brought to you by lying vindictive hypocrites….and Old Navy Performance Fleece,” he jokes. It’s quite odd (and endearing) to see Colbert and Stewart on the same side of the aisle, for once.
Carrying on Kilborn’s legacy, Stewart also features non-political stories, such as Popeye’s marriage and an interview with the munchkins of The Wizard of Oz. He would soon transform the show into mostly political commentary, winning over millions of fans in the process. But even when he’s joking about more absurd things like Popeye’s wife Olive Oil — and her nephew, Lorenzo’s Oil — Jon Stewart is Jon Stewart, an American comedic icon through and through.