There Was No Better Letterman Guest Than Amy Sedaris

Amy Sedaris and David Letterman Photo: CBS Photo Archive/CBS via Getty Images

Last month, David Letterman celebrated the 40th anniversary of the premiere of NBC’s Late Night — and thus the start of his late-night television career — by launching a new YouTube channel featuring classic clips from throughout his 33-year run. It’s a one-stop shop for the dry absurdity of vintage Letterman, whether you want the Olympic spectacle of “Elevator Races” or more scientific segments like the host dropping stuff off a five-story tower. But no Letterman retrospective is complete without the woman whose appearances are late-night legend: Amy Sedaris.

The actress may best be known for projects like Strangers With Candy, BoJack Horseman, and At Home With Amy Sedaris, but her most underappreciated work is her frequent appearances on Late Show With David Letterman, beginning in 2001. At that point in Letterman’s run — post-heart attack and after the wilder days of Late Night — he was a dignitary of the medium. By then, Letterman’s persona was jaded as ever, and he wasn’t one to feign excitement. His guests wanted to impress him, which was no easy feat. But Sedaris did so, and soon enough she became a regular, often filling in at the last minute. By the end of the show’s run in 2015, she was just as much of a fixture as Hello Deli and “Stupid Pet Tricks,” racking up a total of 34 appearances.

Those interviews are some of the best showcases of Sedaris’s chaotically brilliant comedy because it was where her unwieldy, improvisational style could run wild without structural limitations. It wasn’t just thanks to the show but Letterman himself, whose juxtaposing calmness complemented Sedaris perfectly. The chemistry the two shared was one of those rare authentic connections that cut through the overly polished fakeness of late-night TV.

Often without a specific project to plug, the two were able to have genuine conversations that meandered freely in every direction. There weren’t canned answers or rehearsed stories that needed to be prompted, and oftentimes Sedaris would have more control of the interview than Letterman. She’d dive into bits out of left field, ask the host questions of her own, and talk about whatever it was she wanted to talk about while not relying on a question from Letterman for permission. Here, we look back at nine moments from that nearly 14-year run that show what set this duo apart and made Sedaris more than just another guest on Letterman.

Name-Dropping Her Friends in High Places (2001)

Sedaris’s first appearance on the show was to promote a play she was starring in with her friend Sarah Jessica Parker. During these early interviews, this friendship was regular conversation material for Sedaris, who would toss deprecating jokes in the Sex and the City star’s direction, like saying she’d give Parker hand-me-down clothes that were too big, or talking about the chemistry she had with Parker’s husband, Matthew Broderick. When talking about the play the two were in, she said, “She’s already gotten me four tickets to The Producers, which is one reason I’m doing the show. And then I’m gonna try and drive a wedge between her and her husband, Matthew.”

Sedaris would discuss celebrities bluntly and without faux reverence, whether she was talking about raiding Natasha Richardson’s underwear drawer or claiming to have been Jennifer Lopez’s ass-double in Maid in Manhattan: “It’s her face and she does all the acting, but it’s my ass because her ass was so flat and kind of discolored.” Letterman, having spent decades listening to celebrities spew niceties at each other, reveled in these bits.

Giving Dave a Taste of His Own Medicine (2002)

On just her third appearance, Sedaris told a story about how her taxidermied duck named Bill Downs kept getting eaten by the mice in her apartment. Letterman, wrapping up the conversation, said, “I hope you get that straightened out,” and she replied, “Do you?”, deflating the transitional, empty nicety to laughs from the audience and host. It was the same kind of dryness that Letterman himself was known for, often playing the foil to his guests rather than facilitating them. This role reversal of that classic shtick was refreshing and felt like an inside joke to the audience that knew Letterman so well, similar to when Cher famously called him “an asshole.”

The 4 a.m. Neighborhood Tour (2004)

Late Show soon leaned into Sedaris’s personality and asked her to interview artists on the 2003 Grammys red carpet, perform a John Denver song accompanied by Paul Shaffer on piano, and give a tour of her neighborhood during a 2004 sweeps-stunt 4 a.m. taping: “This is one of eleven video porno shops I have in my neighborhood … They just got Internal Sunshine of a Spotless Behind.” It harkened back to the fast-and-loose days of Late Night — back when Dave would go to a store called Just Bulbs to see if they sold shades — and these segments helped establish Sedaris as more than just a guest.

Amy’s Imaginary Boyfriend (2005)

Two of Sedaris’s most common recurring topics on Late Show were her pet rabbits and imaginary boyfriend Ricky. In the case of the latter, there were new developments in the relationship revealed each time, including his untimely death in early 2005. I found a cyst on one of his obliques and I rushed him to St. Vincent’s Hospital … and it was benign. And then we got in the cab and he was murdered on the way home.Just over a year and a half later, she talked about how she now lived with the ghost of Ricky and they were trying to have a baby.

She’d talk about these things — whether true like the rabbits, or a bit like Ricky — with the exact same earnestness as if they both were the most normal thing in the world, sometimes even shooting annoyed glances at the audience if they dared to laugh (like when she said she was a Rockette, or in the case of Ricky, when she brought up his cysts: “Yeah, cysts are hilarious”). 

Bringing a Clip of Paris Hilton Littering (2005)

On one rare occasion, Sedaris did something that was actually typical of a guest on a talk show: She brought a clip. But not from one of her projects — it was a clip of Letterman’s own show from two and a half months prior, when Paris Hilton was a guest. It was at the peak of Hilton’s fame in 2005, and as Sedaris explained to the audience, she spotted Hilton discreetly dropping something behind her chair during her interview with Dave and wanted to share the footage. “She littered. She tossed something on the floor. It’s a rich person’s disease.” It’s the kind of unconventional move that Letterman tried to brace the audience for by introducing Sedaris with the disclaimer of: “She’s peculiar. You have to keep that in mind because she’s — joyfully, gladfully — different than everybody else walking around on the planet.”

Not Giving a Rat’s Ass About King Kong (2006)

In a 2006 interview, Sedaris asked Letterman if he was ever tired of people using his show to promote things. “Yes,” he said, explaining candidly that he didn’t give a “rat’s ass” about the new King Kong remake, which Jack Black was on the show just weeks earlier to promote: “I like Jack Black, but they didn’t invite me to be in their movie to promote my television show — but yet they come on the show to promote their movie.” Letterman told Sedaris that he often feels like a “pimp for motion-picture-distributing companies,” and he’d prefer to interview people who “actually do something with their lives.” Though Letterman was never known for faking enthusiasm, it was still a blunt peek behind the curtain that only someone like Sedaris could elicit.

“I Have Lots of Things to Talk to You About” (2007)

During this 2007 appearance, Sedaris was off to the races the second she sat down, bringing up construction outside her apartment before Letterman could even get a question out. Instead, she plowed ahead to the hypothetical of her staying with him until the work was done, leaning back with her arms crossed, grilling him as if he were the one asking her to move in: “Where do you live? Roosevelt Island?” After a thorough conversation about logistics (“What if I wanted to watch Leno one night?”) and her request to toss a pencil with the show’s signature shattering-glass sound effect, Letterman got a chance to regain control of the ship, remarking, “You’re such a mentally energetic person.”

Interviewing the Interviewer (2008)

Part of what made Letterman and Sedaris’s relationship so unique was that Sedaris was a genuine fan of the show, and she’d light up whenever she could squeeze any personal information out of the usually elusive host. As a result, she was just as likely to be the one asking the questions, if not more so. Once in a while, Letterman would humor her with an answer, and Sedaris would delight in the most mundane of glimpses into his life, like in 2008 when she found out he was building a treehouse: “Okay, don’t say that to me and expect me to leave.”

Amy’s Farewell (2015)

Sedaris’s final appearance on the show, just one month before the last episode in 2015, managed to squeeze in nearly everything that made their pairing so dynamic. “I have like seven minutes and I didn’t leave any wiggle room for you to say anything,” she told Letterman at the top, plowing ahead to a combination of both the expected tangents (like her Spanx flattening out her back because she put them on backwards) and the sentimental appreciations of the host: “You’re a New York staple. You’re like scaffolding!” During that last appearance together at the Ed Sullivan Theater, amid a farewell medley and zodiac readings, she told Dave, “I think about you every single day, since 2001. You’re very important to me.”

There Was No Better Letterman Guest Than Amy Sedaris