Jimmy Kimmel didn’t know what to make of comedian Chris Fleming as he shimmed onto the Jimmy Kimmel Live! set last week, looking like a deranged hybrid of Big Bird and a gender-fluid Howard Stern.
“They told me that this is your first talk show,” Kimmel said as Fleming stared him down with a maniacal grin. “I was concerned that you would even be able to sit in the chair.”
It was a legit concern. The frenetic comedian, promoting his new stand-up special Live at the Palace on HBO Max, did struggle to stay in his seat, whether he was kicking his white shoes up in Kimmel’s face, charging the camera to show off his chipped tooth, or looming over the host à la Jacob Elordi, for a smooch.
It wasn’t that Kimmel was rattled, exactly. He simply had no idea where Fleming might bounce next.
In an era of carefully produced segments, where pre-interviews set up guests for well-rehearsed anecdotes, Fleming’s appearance felt like a throwback to an earlier late-night era when oddball comics like Brother Theodore or Pee-wee Herman might steer David Letterman into uncharted territory.
Paul Reubens had heard that Johnny Carson was “uncomfortable with the Pee-wee character,” Jason Zinoman writes in his book “Letterman: The Last Giant of Late Night,” but Letterman was always willing to roll the dice on weirdos. “He was like the straight man, and I would just go berserk and be crazy around him,” Reubens remembered in the documentary, Pee-wee As Himself.
Berzerk was the point. “I think it’s important to have guests who annoy the public,” Letterman once said about his affection for fringe personalities. “It feels good to scream at the TV once in a while, to go to work and tell everyone how annoyed you are.”
Avant-garde performer Sandra Bernhard loved to flirt with Letterman, though her affections often felt like a threat. Bernhard’s particular love language was “making Dave squirm,” achieved by purposely veering off-script. Letterman’s discomfort was palpable.
“I always wanted to break the norms and really shake people up,” Bernhard recently said on The View about her approach to Letterman appearances. “I couldn’t imagine being any other way. Doing straight comedy was just too boring.”
Norm Macdonald and Sarah Silverman were expert at putting Conan O’Brien on his heels. And Carson didn’t know what to make of Andy Kaufman during the comic’s first appearance in 1977. Kaufman never dropped his Foreign Man persona, even during commercials.
“The character clearly perplexed Carson,” according to “Lost in the Funhouse, The Life and Mind of Andy Kaufman.” The host, who initially believed the Foreign Man character was real, resorted to treating the comedian like a six-year-old, getting laughs while trying to figure out how to handle the eccentric from the made-up island of Caspiar.
Carson caught on, but Kaufman dropped the foreigner act in subsequent visits to The Tonight Show. “This new dynamic throws Johnny,” wrote Kaufman’s partner in comedy crime, Bob Zmuda. “He doesn’t know how to play Andy, and the laughter becomes less and less each time.”
That approach may seem counterintuitive—why appear on Carson simply to bewilder the host? But not every comedian is in it to win the room. In that way, Fleming is a throwback. “We’re focusing too much on numbers, virality, whatever,” the comic recently told Rolling Stone. “If there’s something that I’ve done that you think about or feel later down the road, that’s the key.”
Does that attitude make Fleming a legit successor to those curveball comics of the past? It’s too soon to say. Fleming’s debut segment didn’t reach the uncomfortably surreal heights of a Kaufman or a Bernhard, but its manic energy at least felt delightfully unpredictable.
“I like to keep things surprising,” Fleming says about his approach to comedy. “That’s how I would view it: as a surprise party.”
That spirit of unpredictability is part of the reason comedy-centric podcasts have taken off in recent years—a less produced conversation is more likely to spiral in a funky direction than a carefully choreographed talk-show interview. Fleming’s appearance on Jimmy Kimmel Live! was a reminder that late night thrives when it introduces a little chaos to the mix.
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