In ‘My First Time,’ LateNighter invites veteran entertainers to remember the night they broke into the big leagues of late-night TV comedy.
“Torture.” That’s how Patton Oswalt describes getting bumped at the last minute from his network television debut on Late Night with Conan O’Brien.
Oswalt, still shy of 30 when he booked the gig, had worked out material in a number of New York clubs to prepare for his shot at the big time. He remembers one prep appearance in particular, a show at the Comedy Cellar where a table of women in the front chatted loudly through his entire set.
“I was too nervous to say anything about it,” Oswalt tells LateNighter. “I just wanted to run my material in front of the producers so that they could see I was okay in terms of content and time.”
The comedian tried to ignore the rude women, barreling through punchlines about a hungover Nick Nolte almost appearing in Star Wars, “until one of them screamed at me, ‘You’re not even LISTENING to us!’ Weirdest heckle I ever got.”
After all that work to prepare, getting bumped from Conan at the last minute “was a weird adrenaline dump,” Oswalt says. “I think I was in bed for a day after that.”
Why was Oswalt so nervous? By then, he’d already performed stand-up on several cable comedy shows, including his own half-hour special on HBO. But he says landing a Conan spot was a different animal.
“Late Night with Conan O’Brien felt like a massive step up from the MTV 1/2 Hour Comedy Hour or Comedy on the Road,” he says. “It felt more real, and less of a cattle call. You’re unique, you’re special.”
“With a half hour, you have more time to build your presence, to get the audience to like you,” Oswalt says. “An audience at a taping for an HBO half-hour feels like, ‘Okay, this guy must be legit if he’s filming a whole half-hour special.’ A five- to seven-minute TV spot, you’ve got to prove yourself.”
Oswalt’s chance to prove himself finally arrived—for real, this time—on January 27, 1998.
He spent the anxious hours leading up to the taping running his material over and over in his head. He tried to burn off nervous energy on a hotel treadmill, still practicing punchlines. “It was the only thing I was focused on,” he said. “I was a big fan of Late Night with Conan O’Brien, and that was the kind of place where I really wanted to do well.”
It worked. Watching that first appearance today, you’d never know it was Oswalt’s first time: He confidently delivers a set full of the niche pop-culture references and self-deprecating humor that remain hallmarks of his comedy nearly three decades later. (“My favorite show on television is Xena: Warrior Princess — or as I like to call it, ‘The Patton Oswalt Masturbation Hour.’”)
“If I came off relaxed and self-assured,” he confesses, “then that just attests to my powers of bull-shittery.”
Other than the nerves leading up to showtime, Oswalt remembers little about the actual performance. “I absolutely cannot remember a single thing I said during that set,” he says. “I was swimming in terror and excitement. Just completely outside my head, with adrenaline buzzing in my ears.”
The night’s best moment of unintentional comedy occurred when the 6-foot-4 O’Brien joined the considerably shorter Oswalt to congratulate him on his funny performance. The pair look like a vaudeville act of opposites, with the young comedian barely measuring up to Conan’s chin.
Looking back, Oswalt describes the visual as resembling “an Elven elder who has just signed a treaty with a goblin prince.”
As Late Night with Conan O’Brien rolls credits as O’Brien says his goodnights, Oswalt giggles and points at the cameras like a kid seeing himself on a television screen for the first time.
“That’s right, you’re on TV!” O’Brien assures his gleeful guest. Was that a real moment or was Oswalt just goofing for the cameras?
“Half and half?” Oswalt says. “I was making fun of my actual, goofy-ass excitement that I was trying to sit on in order to look cool.”
He would go on to appear with O’Brien dozens more times, logging a total of 22 visits to Late Night, 3 appearances on The Tonight Show with Conan O’Brien, 19 appearances on Conan, and 3 appearances on Conan O’Brien Needs a Friend.
Watch the Late Night set that started it all below:
