You could probably tell Aubrey Plaza was going to be a pantheon weirdo talk-show guest by the way she got her Parks and Recreation role. Producer Michael Schur told AV Club that Aubrey came over to his office and “made me feel really uncomfortable for like an hour.” The same hilarious awkwardness that inspired Schur to create April Ludgate is what helps Plaza knock it out of the park every time she shows up on Fallon or Kimmel. Who else brings the quirk? Check out Aubrey and 24 more of the best weirdo guests in talk-show history. 

Crispin Glover

There was always an extremely thin line between the real (?) Crispin Glover and the eccentric oddballs he played in movies like Back to the Future and River’s Edge. He was notorious for a rambling interview with David Letterman, who Glover offered to arm-wrestle before launching a karate kick that nearly landed in Letterman’s face. “I think I’m going to go check in on the Top 10,” said Dave as he left his bizarro guest alone on the set. 

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Glover's inseam somehow survived the kick.

Ye

The artist formerly known as Kanye West has had a number of, shall we say, quirky talk show appearances in recent years. There was his eight-minute monologue on Ellen as the host sat there slackjawed, touching on subjects ranging from Picasso to Payless Shoes. He also had a classic on Jimmy Kimmel Live when Kimmel asked Ye why he believed Donald Trump cared about Black people. The response was several seconds of silence before Jimmy mercifully cut to commercial. 

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Pretty much Ye's response to the Trump question.

Sandra Bernhard

Bernhard’s appearances on the first iteration of Dave Letterman’s show were more like wrestling matches than interviews. Part seduction, part poke in the eye, Letterman/Bernhard exchanges always promised to devolve into anarchy. It’s a wonder she never devoured Paul Shaffer.

Joaquin Phoenix

A Hall of Fame weirdo talk show guest, Phoenix recently got into it with Jimmy Kimmel over a Joker clip that showed him berating the film’s crew. But that can't top his David Letterman appearance when the heavily bearded Phoenix announced that he was leaving acting to become a rapper. He goes from seemingly confused to actually angry in an is-this-real? appearance for the ages. 

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Are we sure that Andy Kaufman isn't underneath all that hair?

Andy Dick

Sure, he’s been obnoxious on talk shows plenty of times but it’s only when Andy insisted on fondling Ivanka Trump’s glittery calves that Kimmel security had to physically remove him from the set. A true Dick move.

Drew Barrymore

Back in the days when she was a Hollywood wild child, Drew helped Dave celebrate his birthday by jumping onto his desk and flashing her Barrymores. “Thank God, he threw his head back and laughed,” Barrymore wrote in her biography, Wildflower. “This was a true moment of freedom. And it got to be something fun rather than something wrong. Thank you for that, Dave.” 

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And some part of Steven Spielberg died that day.

Dakota Johnson

It’s not so much that Dakota does awkward interviews as she refuses to stand for hosts’ bullshit. When Ellen sort-of-jokingly complained that she wasn’t invited to Johnson’s birthday party, Dakota called her out. “I did invite you and you didn’t come.” Ellen insists Dakota is wrong before her own producer admits that she was invited. And watching a red-faced Ellen squirm is what all good children deserve for Christmas every year. 

Madonna

Sandra Bernhardt’s occasional talk-show tag-team partner took great pleasure in sticking it to Letterman in the 1980s. “Why are you so obsessed with my sex life?” was a typical opening, and then it generally devolved from there. How many guests have called Letterman a “sick f***” on the air? We can think of one.

Norm Macdonald

Norm was hilarious as a guest, but things could get extra-weird when it was someone else’s turn to talk. Poor Courtney Thorne-Smith could barely promote her new Carrot Top movie (yes, there was a Carrot Top movie) before Norm becomes an agent of chaos and turns the entire show topsy-turvy.

Courtney Love

 

Our final body-baring guest is Love, who fake-flashed Letterman in 2004 and liked it so much that she kept going with several actual flashes over the course of her interview. It was a “whoa!” moment when Drew bared all in 1995, but this one barely registered an angry phone call from the FCC. 

Borat

 

No sign of Sacha Baron Cohen when it came time to promote Borat! Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan. Instead, it was the titular character himself in a talk-show appearance that manages to flap the usually unflappable Dave. (Not many of Letterman’s guests enjoy taking photographs of ladies while they make toilet.) And who knew Paul Shaffer was the biggest music star in Kazakhstan?

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“My wife died. High five!”

Farrah Fawcett

 

Poor Farrah was either inebriated or having a minor stroke during her 1997 Letterman appearance. There are several nominees for the interview’s weirdest moment, but we’ll go with the point where she stops speaking for several seconds to gaze at the skyline mural behind Letterman’s desk. She gave a gobsmacked “wow,” mistaking it for a real window with a view of New York below. 

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Farrah discovers Manhattan

Lady Gaga

 

During the pandemic, Jimmy Fallon got his guest Gaga on Facetime to announce a global benefit for healthcare workers. Except, oops, it really wasn’t a convenient time for Gaga to chat. A confused Fallon, who clearly had prearranged the live interview, had to navigate his guest telling him, “it’s just like a really weird time. Am I on TV?”

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Pandemics are hard.

Tony Randall

 

Randall’s comic persona on shows like The Odd Couple was an overly uptight, highly educated prude, the Frasier Crane of the 1970s. But Letterman gave Tony a chance to embrace his weirdo side, showing up on random nights for stupid stunts or Viewer Mail cameos. Who knew Randall was actually kind of cool?

Cher

 

If there was anyone who genuinely disliked David Letterman more than Madonna, it was likely Cher. It took Letterman years to get her to agree to appear on the show, primarily because she thought he was an insufferable asshole. And when she finally showed up, she told him to his face. In fact, it became a tradition.

Aubrey Plaza

From getting personal with Robert DeNiro’s nipples to her summer of so many penises, Plaza has a singular gift for making talk show hosts hilariously uncomfortable. Many of the weirdo guests on this list have a signature clip -- Aubrey has compilation reels. All hail the Queen of Cringe.

Top image: Conaco

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