Conceived as a bit for Damon’s upcoming appearance on Letterman’s Netflix talk show, My Next Guest Needs No Introduction, the unobtrusive shot nevertheless took enormous planning—and fulfilled Letterman’s lifelong dream of being an extra. According to Vulture, the talk show legend has been dreaming of doing the thankless job of background actor ever since he saw his good friend, comedian Gary Mule Deer pop up in a shot of Woody Allen’s 1977 film Annie Hall. (Mule Deer is a patron at the health food store where Allen’s Alvy Singer unsuccessfully tries to get Diane Keaton’s Annie to come back to New York.)
Says My Next Guest Needs No Introduction showrunner Isabel Richardson, Dave was “tickled by the fact that this guy was recognizable to him in the shot, but that most people probably didn’t recognize him.” And thus a five-decade quest was born, with Letterman’s camp pitching the idea to a receptive Damon in advance of his sit-down with the host later this year.
Not that it was easy, as Richardson noted that her staff finally used their connections to The Gilded Age crew to secure the unusual request. According to Gilded Age executive producer Kate Churchill, “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.”
Richardson, noting that it was Damon’s early extra work alongside friend Ben Affleck that cemented the cameo idea in her mind, pulled all the complicated strings necessary to line up the schedules of two busy stars and an elaborately costumed HBO period drama, but in the end, Letterman got his wish as he and Damon are now forever enshrined as two natty businessmen likely hurrying to negotiate high tariffs and have their facial hair meticulously groomed.
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