THE WELL-BORN IDENTITY

Oscar Winner Looks Unrecognizable in 1880s Makeover

The A-lister completely transformed for a dapper cameo.

Matt Damon has transformed from a Massachusetts townie to an 1880s gent.

The 56-year-old Good Will Hunting star made a nearly unrecognizable cameo in the background of a transition scene during the Season 4 premiere of HBO’s The Gilded Age.

In the clip, Damon and David Letterman went undercover as two sharp-dressed, cane-carrying men crossing the street.

The Gilded Age overhauled both men’s appearances to fit into the show’s 1880s New York City setting, dressing them in dapper waistcoats and leather gloves. Letterman wore a bowler hat from his own collection while Damon donned a top hat.

The key, however, was their facial hair.

Executive producer Kate Churchill told Vulture that the hair and makeup team ran into an issue when trying to make the two men appear period-appropriate.

“Now Dave’s easy; he has this fabulous beard,” she said.

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Churchill called My Next Guest Needs No Introduction With David Letterman showrunner Isabel Richardson to make sure he maintained his facial hair, which Letterman has upheld for over a decade.

“I called Isabel and said, ‘Tell Dave not to shave,’ and she was like, ‘Not a problem,’” Churchill recalled.

But the team struggled more with Damon.

Churchill said that Damon had just shaved off his “fabulous beard” from The Odyssey the weekend before filming in May.

The hair and makeup team eventually camouflaged him with a thick mustache and sideburns.

The A-listers ended up on set because Letterman had long wanted to get a gig as a background actor.

He saw his opportunity when he booked Damon as a guest on his Netflix show. Damon started his acting career as an extra alongside longtime friend Ben Affleck.

They filmed their day on set for an episode of the talk show, which will air later this year.

“Dave was like a kid in a candy shop on the set. He was so excited and curious about everything,” Churchill told the outlet.

Richardson added, “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.”

Damon also underwent a face and body transformation to portray the titular character in Christopher Nolan’s 2026 box office hit, The Odyssey.

“I used to walk around at between 185 and 200 [pounds], and I did that whole movie at 167,” Damon told NFL stars Travis and Jason Kelce on their New Heights podcast. “And I haven’t been that light since high school. So it was a lot of training and a really strict diet.”

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One of his main dietary changes, he said on the Good Hang with Amy Poehler podcast in July, was quitting gluten.

“It completely changed my life these last couple of years,” he said, explaining that, although he missed some foods and beer, he felt better with the new diet.

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Roosa RahkonenReporter, The Looker

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