Remembering the time Regis Philbin dressed up like Shrek to make his pal Dave Letterman laugh

In addition to his veritable mountain of talent as a TV host and entertainer, Regis Philbin—who died earlier today, at the age of 88— is a pretty easy shoe-in for the Great Talk Show Guest Star Hall Of Fame. Nowhere was that clearer than in the more than 150 appearances he made on his pal Dave Letterman’s Late Show, a relationship that stretched from the series’ fifth episode, all the way up through its second-to-last. The perfect, endlessly excitable foil to Letterman’s detached deadpan, Philbin was game for anything, as long as it might possibly get Letterman to laugh. Which brings us to one of the finest moments in either man’s career: The time Regis Philbin spent 2.5 hours in a makeup chair so he could dress up like Shrek for Dave Letterman’s amusement.

For context, this was back in 2009, when Shrek The Musical fever was sweeping the nation, probably. Philbin—still hosting Live! With Regis And Kelly at the time—was doing a series of shows from Broadway, and so he consented to be en-Shrek-ified for an appearance on Letterman’s show. Thus begins one of the most surreal moments in the history of late-night talk (and yet, somehow also only the second weirdest interaction Letterman ever featured with a man painted bright green).

“Biggest mistake I ever made,” Philbin mutters as he trundles his way into his seat, clearly enjoying his own mounting frustration at the ridiculous waste of time that is this entire bit. It’s got it all: spittakes, invitations to debauchery, and a transcendent moment of Letterman shutting down Philbin’s half-hearted efforts to plug his show. “How do I look?!” the bright green Philbin booms, in his typical vaudevillian fashion—only to be hit by the most casual, faux-bored “You look fine” ever offered up in TV history. It’s a perfect little window into the two performer’s relationship, and a quick encapsulation of the grouchy-but-endless energy that made Philbin such a television superstar.