On January 11 1999, when Jon Stewart took over as host of The Daily Show from Craig Kilborn, no one could have predicted that, 16 years later, Stewart would become an icon of satire. Under

Kilborn, the show was more of a parody of a weekly news magazine: the jokes were often slapstick and lacked any broader political point. That would all change the day Stewart stepped in.

While the first show certainly wasn’t as slick as its later iterations, it was clear that Stewart possessed a unique brand of political satire. The Kilborn version of The Daily Show was far

less politically oriented, and often included silly segments (like the recurring “This Day in Hasselhoff History”). The first episode with Stewart acts a segue between that sort of classic

year: the impeachment trial of President Bill Clinton. We learn right away that Stewart isn’t going to accept political rhetoric and blustering, and will be keen to identify faulty logic and

partisan spin. He satirically points out to viewers that the key question will be how the Republicans can take a “pointless, tawdry trial whose outcome had already been decided and make it

last.” Next, we get a glimpse of a refashioned Stephen Colbert. Under Kilborn, he’d assumed the character of a doltish correspondent. Now, reporting from the steps of the Capitol on

Clinton’s impeachment trial, Colbert dives directly into political satire. Stewart asks Colbert to report on whether the trial is being framed by bipartisan agreement or partisan bickering.

Colbert responds that the trial is actually being framed by “merchandising and product placement.” “The Democrats are being brought to you by Chili’s El Diablo baby back rib fajitas,”

Colbert says. “The Republicans are being brought to you by lying, vindictive hypocrites and Old Navy performance fleece.” Certainly – as we can see from that clip – Stewart wasn’t pulling

any punches: he was highlighting political buffoonery and the role of big money in politics, while going after both sides. But as Colbert would later point out in an interview with IGN, on

Stewart’s first day the show had the same writers, the same executive producer (Madeleine Smithberg) and the same correspondents that Kilborn had. It was – as Colbert put it – “a gradual

evolution.” He recalls Stewart saying, “Let’s see if we can’t maybe make the field pieces reflect something that’s happening in the headlines of the day, so there’s more of a natural

transition, the show doesn’t change tonally, completely.” Yet on that first day Stewart made a point of telling the audience directly that the show was going to be different. Stewart’s

hosting debut included an interview segment with guest Michael J Fox, and it would give us a glimpse of the exact sort of rapport that would characterize much of Stewart’s interaction with

guests – namely, Stewart’s refusal to follow a predictable script. Next came an example of what would become perhaps Stewart’s most defining quality: his sharp critique of the media. In the

segment This Just In, he covers the death of the “Native American” actor who wept on the 1970s-era Keep American Beautiful ads – pointing out to viewers that the actor was actually an

Italian-American. Meanwhile, the title of the bit – Sitting BULLS–T! – includes the sort of puns characteristic of Stewart’s writing team. And, like always, the show ended with a moment of

Zen. From day one, it was clear that Stewart was bringing something new and exciting to television. The only thing missing from this first episode was a Fox News zinger (though Stewart would

certainly make up for that over the next 16 years). Now with Stewart’s Tuesday announcement that he’ll be stepping down as host, the The Daily Show’s future is in flux. Who will be the next

host? Will there even be one? And will he or she attempt to replicate Stewart’s brand of humor, or try to reinvent it? Either way, let’s hope that we’ll still have our moment of Zen.