Amy Sedaris: The Last Great Late Night Guest

Amy Sedaris perfected the craft of the late night guest spot long before it turned into a banal excursion of parlour games.

On September 6, 2001, Amy Sedaris wandered onto the Late Show with David Letterman set for her first appearance.

She was there to plug a play she was starring in alongside Sarah Jessica Parker. It was one of the few times she was actually on the show to plug a project.

"It’s so nice to meet you," she said to Letterman, "I brought you some chocolates."

From there, Sedaris didn’t miss a beat. As Letterman complimented her outfit she stood up, giving the audience a better look after telling the host with a wink, "Looks better on the floor Dave, looks better on the floor".

Letterman was a unique giant in the late night world. He wasn’t the type to be overwhelmed or impressed by fame when it came to his guests.

New York Times columnist Jason Zinoman described him as "almost resentful that he had to talk to these people".

Sedaris would often leave him speechless.

Amy Sedaris Is The Last Great Late Night Guest
Sedaris showing off some of her facial impressions. Left: Jennifer Aniston. Right: "Ask me 'why the long face?'" Image: CBS via YouTube.

Letterman forged a path many have refused to go down and didn't worry about clashing his guests, despite the invisible handshake between late-night hosts and guests as a publicity machine.

These were guests in Letterman’s house, and he would push the buttons he saw fit. It resulted in handfuls of memorable interviews where the gruff host refused to pander. There are lists of the most disastrous, uncomfortable, contentious and tensest interviews Letterman conducted. 

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Letterman was no angel, to be fair, he goaded his guests and got great joy out of mocking some of Hollywood's biggest names to their faces. For that, Cher called him an asshole, Madonna smoked a cigar in his face and swore a record amount of times to punish him. 

While he found his glee in his detached, provocation of his guests, there were also the days where you could see him at his most uninterested. This often occurred during the late night staple: the anecdote.

It's something that was perfectly dissected by comedian Nathan Fielder when he stopped by Jimmy Kimmel Live, going so far as to spend $350,000 to orchestrate the perfect late-night story.

The performative relatability of celebrities sharing their humorous stories was never something Sedaris struggled with. She wasn't trying to be relatable, she was trying to market.

Since Letterman’s departure from the late-night space in 2015, the genre has changed dramatically. Now no longer interview-based, the late night staples of Fallon, Kimmel, Conan, Corden et al are geared more toward generating viral moments to be clipped and posted across the internet.

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There are exceptions to the overwhelming standard, with Girl’s Trip breakout star Tiffany Haddish’s story about a Groupon swamp tour on Kimmel became such a favourite with audiences Groupon decided to make her the star of their Superbowl commercial.

All that brings us back to Amy Sedaris. The off-kilter comedian appeared on Letterman 34 times in 14 years. Her appearances are like electric shocks to the system as she locks eyes with Letterman, and tells the most absurd stories with incredible sincerity.

"I got a new rabbit," she said eagerly in a segment from 2003. "You know, my other one was murdered, so I finally got a new rabbit and her name’s Dusty. I got her from a shelter... so she’s a bit iffy."

In Letterman's now infamous 4 am special, Sedaris gave a tour of her neighbourhood, Greenwich Village.

"This is one of 11 video porn shops I have in my neighbourhood," she told Letterman as she roved around the street in the middle of the night," they have all the latest videos -- they just got 'Eternal Sunshine of the Spotless Behind'."

Like her brother David, storytelling is in Sedaris' blood. The most ordinary question ("Do you go to sporting events?") results in a tale of a stiltwalker slipping on an olive.

Casually she mentions to Letterman, "You know Ricky -- my imaginary boyfriend -- we've been trying for years to have a baby...".

Sedaris would buck the framework of the anecdote and the guest visit, telling Letterman about her long-term relationship with Ricky, her rabbits or the reason she could never have an imaginary dog. She’d tell him how she decorated her hallways with candy wrappers, put a screen door on her bedroom, each time delighting Letterman with her peculiarities.

Often she wasn't even there to promote anything, she always had a dress hanging on the back of the door in case they called.

In one appearance she wore an enormous tulle-lined gown and brought with her a prepared clip, totally normal behaviour until she revealed it was a clip of Letterman's own show.

"I'm the person who watches your show," she joked, "that girl Paris Hilton was on your show not too long ago and she littered... it's a rich person's disease but I brought a clip to show you because no one else noticed but me."

Sedaris described her appearances on the show as just being "in the moment" and "like a live date". "I like it when you do something like that and you forget there's an audience in front of you," she said.

There have been efforts to recreate Sedaris' incredible interviews, she has appeared on other late night shows and her long friendship with Stephen Colbert makes for gorgeous viewing, but nothing stands up to the dynamic duo of Letterman and Sedaris.

Now late night has shifted drastically with the new school of hosts, as Corden and Fallon push their guests away from conventional interviews and toward parlour games to be chopped up and shared online.

The requirements of celebrities to be actually interesting people becomes less of a challenge when they're gifted the opportunity to simply sing in a car or play a game.

While it saves us from the otherwise exhausting rigour of boring celebrity interviews, it truly does feel like we'll never have a dynamic like Sedaris and Letterman on late night.

But it's more than that. Sedaris brought out the best in Letterman. Despite their friendship only existing in these 15-minute intervals, it's a friendship that was so perfectly realised even if it was only for a few minutes at a time.

Late night seems to have wandered from insights into the lives of stars to viral content machines. While Sedaris has continued to pop up on other shows, no other appearance has managed to reignite that perfect chemistry she had, the unmatched ability to chip away at Letterman's tired exterior.

"If it were up to me you'd be here every night," he said in 2006, before quickly adding, "Well, every other night."

Feature image: CBS via Getty Images.