Credit: Will & Grace: Chris Haston

Memorable ”Will & Grace” guest stars: Matt Damon

If you’ve ever wanted to hear Matt Damon sing, this 2002 episode is the one for you. He plays Owen, Jack’s rival for a solo spot in the Gay Men’s Chorus. He’s also a ringer; despite his protestations that he’s ”as gay as the locker room at the Ice Capades,” Owen is just a straight guy who likes choral music. Jack outs him in front of the rest of the singers after catching him in a compromising position with Grace (whose seduction of Owen goes comically awry), but the move backfires: The choir accepts Owen anyway out of tolerance. (And because he’s hot.)