The Gilded Age added two glittering new stars to its season 4 premiere: Oscar winner Matt Damon and Emmy winner David Letterman.
The Odyssey star and the former Late Show host made a surprise cameo appearance together — even if just for a few seconds — in the Sunday, November 1, episode of the HBO drama. They can be seen walking across the famous New York City road where the show’s powerhouse centerpiece families, the Russells and the Van Rhijns, live.
As for the how and why, apparently, it’s all down to Letterman, 79, and his dream of being a background actor.
My Next Guest Needs No Introduction With David Letterman showrunner Isabel Richardson told Vulture in an interview published Sunday that the comedian has long wanted to make a cameo in a film or TV show. Letterman was inspired by seeing comedian Gary Mule Deer in a blink-and-you’ll-miss-it scene in Annie Hall.
Richardson said that Letterman angled for cameos in Wes Anderson‘s movie The Phoenician Scheme, Michael B. Jordan’s upcoming The Thomas Crown Affair and Netflix’s Black Rabbit starring Jason Bateman, but none of them materialized.
The Gilded Age cameo came about after Richardson and the team for Letterman’s talk show began researching Damon, 56, for an upcoming episode, discovering he began his career doing background work.
“We thought, ‘Okay, this could be the perfect opportunity. 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,” said Richardson, adding that Damon “unequivocally chose this idea as his favorite” from a list of segments for his episode.
A line producer on My Next Guest reached out to a friend who worked on the HBO drama with the idea, which eventually found its way to executive producer Kate Churchill. The cameo was approved by Gilded Age creator Julian Fellowes and HBO, and the actors filmed their scene on a closed set “where we control everything, and the public doesn’t have access,” said Churchill.
“When you watch the show, you’ll see both Matt and Dave came alive in a way. Dave said, ‘I hate trying on clothes; I’m really dreading this,’” Richardson said. “And the second he got there, he was elated.”
“Dave was like a kid in a candy shop on the set. He was so excited and curious about everything,” Churchill recalled.
According to 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.”
The Gilded Age season 4 airs Sundays at 9 p.m. on HBO and HBO Max.
