This Is the Moment Jon Stewart Became ‘Daily Show’ Jon Stewart

We’re just days away from the White House Correspondents’ Dinner, the annual celebration in which Washington elites get to pretend that they have a sense of humor for one night a year. As we’ve mentioned before, the 2024 gig belongs to Colin Jost, who was either picked because of his work on Saturday Night Live’s Weekend Update, or perhaps the White House Correspondents’ Association just assumes that Biden is a big fan of Tom & Jerry.

The event’s intersection of comedy and politics has naturally led to a number of Daily Show regulars being asked to host — from Roy Wood, Jr., to Trevor Noah, to Stephen Colbert, who famously torched George W. Bush while standing like five feet away from him. Perhaps not coincidentally, the following year, the dinner opted for the non-confrontational humor of impressionist Rich Little.

But what about the original – not counting Craig Kilborn, obviously – Daily Show host? Well, Jon Stewart hosted the event way back in 1997. But, at the time, he was far from the obvious choice. Stewart only got the job because Rosie O’Donnell pulled out at the last minute for unspecified “personal” reasons. Organizers were “miffed” and “nervous,” following news of her departure, so they approached everybody’s favorite topical comedian and fake newscaster… Dennis Miller. When he said “no,” they went with Stewart instead.

Incredibly, the man who would go on to become one of the most politically-influential comedians of his generation was described by the Washington Post as “not primarily a political jokester,” although they noted that he “promised to work in a few White House and congressional gags” at the dinner. To be fair, this was back when Stewart was still mostly known for his MTV talk show, and for popping up in random acting roles, like the time he guest starred on The Nanny. 

Looking back at his performance today, it’s impressive how the young Stewart effortlessly mocked major political figures to their faces without a trace of unease. The jokes were well-informed and cutting; he poked fun at current scandals of the day, lambasted the Clinton administration’s inefficacy and referenced 1995’s Million Man March, “or, as many of you probably remember it, ‘that day we called in sick,’” Stewart deadpanned. 

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In retrospect, it’s hard not to see this as the moment that Jon Stewart became the Jon Stewart of The Daily Show. In just one night, he went from an apolitical dude in a leather jacket to a cutting, observant, politically literate voice. He took over The Daily Show just two years later, but in between, he still found time to play an alien educator who gets stabbed in the eye with a ballpoint pen by teen heartthrob Josh Hartnett while leaking several gallons of 2 percent milk from the wound. 

Ah, the ‘90s. 

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