Matt Damon and David Letterman, What Are You Doing in The Gilded Age?

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Wedged between Jack’s gentleman lessons, a dalliance that could ruin Marian, and a surprise hysterectomy, The Gilded Age season-four premiere’s most shocking moment is a blink-and-you-miss-it cameo. Two, actually: Matt Damon and David Letterman.

No, really! Eight minutes and 33 seconds into the episode, Damon and Letterman play gentlemen silently crossing the street as the camera pans to the home of George Russell, who’s recovering inside after getting shot at the end of season three. The six-second star turn is all you’ll glimpse of the late-night host and Academy Award–winning actor. Even though The Gilded Age is packed with stars, they usually have speaking roles. How did Damon and Letterman end up in the episode?

Through a lot of behind-the-scenes scrambling, according to Gilded Age EP Kate Churchill and Netflix’s My Next Guest Needs No Introduction With David Letterman showrunner Isabel Richardson. It all started with Letterman’s nearly 50-year-long quest to become a background actor.

Back in 1977, Richardson explains, Letterman spotted his friend, comedian Gary Mule Deer, in a scene in Annie Hall. Letterman was “tickled by the fact that this guy was recognizable to him in the shot, but that most people probably didn’t recognize him,” she says. In recent years, there have been several close calls with Letterman getting cast for background work, starting with Wes Anderson’s The Phoenician Scheme. Letterman was friends with Richard Ayoade and Bill Murray, who starred in the film, and he thought he could “go hang out on set, it’d be a fun story, and he could be in the background of a Wes Anderson movie,” Richardson says. But the dates didn’t work out.

Next up? While shooting an episode of My Next Guest with Michael B. Jordan, Letterman tried to cameo in the upcoming remake of The Thomas Crown Affair. Though “Michael tried very valiantly to make it work,” Richardson continues, the dates once again didn’t line up. Then there was Jason Bateman. “Dave was walking home in New York City, and he happened to come across the set of Black Rabbit, Jason’s show,” Richardson says. “We have pictures of him — he sat down on set, he watched it all unfolding. He asked a PA to put him in the shot, to no avail.”

When Richardson and the My Next Guest team started researching Matt Damon (whose episode premieres later this year), they discovered that Damon started his career as a background actor alongside Ben Affleck. “We thought, Okay, this could be the perfect opportunity,” Richardson says. “It’d be really fun for Dave to do this with Academy Award–winner Matt Damon, and it tied into his origin story really well.” The actor was equally game. Presented with a list of possible field segments for the episode, Damon “unequivocally chose this idea as his favorite. And this was by far the silliest, most ridiculous idea.”

The next hurdle: Finding a show for Damon and Letterman to cameo on. While looking at a list of every movie and TV show filming in New York during My Next Guest production, Richardson immediately clocked a personal favorite, The Gilded Age. Adam Donnelly, a line producer on My Next Guest, had a friend working on the show and soft-pitched the idea, Richardson explains. The request ended up with Churchill, who became responsible for making it happen. “It was a kind of hysterical moment when our production supervisor Leah Baker came up to me on set and was like, ‘Well, I have a kind of funny, interesting question: Would you like Dave Letterman and Matt Damon to be background on our set one day?’” Churchill remembers. “I just started laughing.”

Churchill took the idea to Gilded Age showrunner and creator Julian Fellowes as well as HBO head of drama Francesca Orsi and CEO Casey Bloys. Everyone thought it was “hysterical,” but Churchill recognized that having David Letterman and Matt Damon in the scene ran the risk of distracting the audience. “The only way I could think of was if we did it in a very controlled manner and it was a shot that we needed, so there was a high chance of it making the cut,” she says. She wanted to make sure the scene would film on Gilded Age’s “hero street,” the set showing the main road where the Russells live across from the Van Rhijns. The back lot located in Old Bethpage on Long Island is “where we control everything, and the public doesn’t have access,” she says. That made scheduling tricky: “There’s a very specific number of days that that could happen, and our schedule is set. I went back to Isabel like, ‘These are your choices of days, and it has to work for both these guys.’

“I have to really give credit to our studios because a simple idea was actually quite complicated,” Churchill continues. “Things like, Matt had to be paid as a background person, but of course he works under his own company. There were a lot of emails going around, but people really locked arms, and both studios saw that it was a fun collaboration where we could help each other.” Richardson agrees: “It would have been really, really easy for them to say, ‘This is way too complicated, this creates too many headaches for us. Fun idea, but no thanks.’ And they did the opposite.” 

While Richardson and Churchill kept an eye on their respective email threads, Churchill worked with The Gilded Age’s hair and makeup team to ensure Letterman and Damon looked period-appropriate. “Now Dave’s easy, he has this fabulous beard,” Churchill says, “I called Isabel and said, ‘Tell Dave not to shave,’ and she was like, ‘Not a problem.’” Damon, on the other hand? That was a problem. The actor was coming right off The Odyssey with Odysseus’s “fabulous beard,” as Churchill puts it, but he had already shaved it for Saturday Night Live the weekend before his Gilded Age scene would shoot. The HBO show’s hair-and-makeup team went to work, crafting period-appropriate facial hair.

The process wouldn’t be as simple as Letterman and Damon dropping by on the day of the shoot. They needed to come in for a fitting just like every other background actor on The Gilded Age, Churchill explains — the show’s costume designer, Kasia Walicka-Maimone, insists on it. That potential problem turned into an opportunity for My Next Guest, which filmed the behind-the-scenes moments for its own episode. “When you watch the show, you’ll see both Matt and Dave came alive in a way,” Richardson says. “Dave said, ‘I hate trying on clothes; I’m really dreading this.’ And the second he got there, he was elated.”

Plus, there was one aspect of the costume Letterman got to take care of himself: a bowler hat he had custom-fitted at “the oldest hat shop in London” while shooting his episode with Michael B. Jordan. The Gilded Age costumers deemed it period appropriate, so the bowler hat seen onscreen is Letterman’s own.

The day of production finally arrived in May. Churchill remembers, “Dave was like a kid in a candy shop on the set. He was so excited and curious about everything.” Adds Richardson, “Matt Damon was laughing so hard throughout the day, and he had this mustache on, so anytime he laughed, he would have to hold on to his mustache to make sure it didn’t come loose.” 

Calling it “a huge act of generosity” for Damon to “schlep outside of the city on a day off,” Richardson remembers him pointing out to Letterman that “this is not a normal background experience. Background actors don’t normally get their own trailers.’” Adds Churchill, “It really was one of those rare moments in our business where everyone’s having a lot of fun doing something special, and there was this great authenticity to it that felt very specific to these two shows.” 

So would Letterman be credited as David Letterman or as “Earl Hofert,” the pseudonym he used for his more extensive appearances in Cabin Boy and Beavis and Butt-Head Do America? Richardson laughs. “I don’t want to speak for Dave, but my guess would be that he’s incredibly proud of the work he did on The Gilded Age, and he would want to be credited as David Letterman because he wants that in the style of Gary Mule Deer. He wants that ‘Is that that guy moment?,’ and then afterward you can confirm that it is in fact that guy.”

Churchill jumps in: “I hate to break it to you guys: They’re background actors. I don’t know that we gave them a credit.” HBO confirms they didn’t. 

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