It was the cameo nobody saw coming. Viewers were left shocked and bewildered when Matt Damon and David Letterman popped up around eight minutes into the Season 4 premiere of “The Gilded Age” as a pair of suited-and-boot background actors. The duo’s silent appearance in the HBO series (which was created by “Downtown Abbey” mastermind Julian Fellowes) came about thanks to Isabel Richardson, the showrunner of Letterman’s “My Next Guest Needs No Introduction,” who decided to try and make a long-time dream of his come true.
Richardson told Vulture that Letterman has been trying to get hired as a background actor ever since he watched “Annie Hall” and saw his friend, comedian Gary Mule Deer, in the background of a scene. He was “tickled by the fact that this guy was recognizable to him in the shot, but that most people probably didn’t recognize him,” Richardson explained. She revealed that Letterman almost appeared as a background actor in Wes Anderson’s “The Phoenician Scheme” thanks to his friendships with Richard Ayoade and Bill Murray, but the dates didn’t work.
Richardson and her team focused on Letterman’s background acting dream again when researching an upcoming episode of “My Next Guest” with Damon. They learned that the Oscar-winning A-lister began his career in the background of scenes and floated the idea of him accompanying Letterman in a scene for a full-circle journey filmed for the talk show. Damon “unequivocally chose this idea as his favorite,” Richardson said. “And this was by far the silliest, most ridiculous idea.”
The location of the cameo was carefully chosen
When the background cameo idea was confirmed, Isabel Richardson’s team had to find a production filming at the same time as they were shooting Matt Damon’s “My Next Guest Needs No Introduction” episode, and then get that production’s team on board. Speaking to Vulture, “The Gilded Age” executive producer Kate Churchill recalled the moment she was approached about the idea of the famous duo appearing in the background of her show. “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?’ I just started laughing.”
Churchill got the green light from the higher-ups at HBO and it was all set. She decided to film on the “hero street” set (the main road where the Russell family lives across from the Van Rhijns) as it’s located on a back lot in Long Island with no public access. “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 explained. Scheduling was tight and there was a lot of red tape, but it all worked out. Letterman even got to wear his own custom-fit bowler hat, with the show’s wardrobe department deeming it period appropriate. The “My Next Guest” cameras filmed the costume fitting, which turned into a joyous occasion. “When you watch the show, you’ll see both Matt and Dave came alive in a way,” Richardson said.
