Matt Damon and David Letterman appeared about eight minutes into the Season 4 premiere of HBO’s The Gilded Age, playing suited background actors in a brief, silent cameo. The appearance grew out of Letterman’s longtime interest in being hired as an extra, according to Isabel Richardson, showrunner of My Next Guest Needs No Introduction.
Richardson told Vulture that Letterman had wanted to try background acting since seeing his friend, comedian Gary Mule Deer, in the background of a scene in Annie Hall. Letterman was amused that he could recognize Mule Deer while many viewers might not, she said. He had nearly taken a similar role in Wes Anderson’s The Phoenician Scheme, but scheduling did not work out.
Richardson’s team revisited the idea while preparing an upcoming My Next Guest episode with Damon. They learned that Damon had started his career appearing in the background of scenes and suggested that he join Letterman for a cameo as a full-circle moment to film for the talk show. Damon chose the idea as his favorite, Richardson said.
The team arranged the appearance with The Gilded Age while filming Damon’s interview. Executive producer Kate Churchill recalled being asked whether the actors could appear as background performers and said she laughed at the proposal. After receiving approval from HBO, the production selected the show’s “hero street” set, where the Russell family lives across from the Van Rhijns. The backlot location on Long Island had no public access, allowing the cameo to be filmed under controlled conditions.
Scheduling and production approvals made the plan complicated, but it went ahead. Letterman wore his own custom-fit bowler hat, which the show’s wardrobe department considered appropriate for the period. Cameras from My Next Guest also filmed the costume fitting. Richardson said both men came alive during the experience.
Sources: TVLine.