Few things are more cringe-worthy than when celebs try to imitate their actor pals. But when done right… genius! Recently, Matt Damon’s quickie take on Matt McConaughey on Letterman had more humor than all 56 hours of Damon’s The Good Shepherd combined. And on Monday, and also on Letterman, Jim Carrey took a break from promoting The Number 23 to show off his David Caruso as Horatio Caine impression. Though his scary scarecrow hair was a bit distracting, his intonation (“Well I guess we’ve… found our man”) of the CSI: Miami star was spot on. There’s something cheesily fantastic about Caruso’s kickers (which can be seen in all their glory here and here). They lack the sardonic wit of a Det. Lennie Briscoe send-off (RIP, Jerry Orbach), but how can you not be amused every time Caruso whips out those black sunglasses?
Of course, Kevin Spacey can ape just about any of his famous friends (and is frequently asked by talk-show hosts to do so), and Kevin Pollak’s Peter Falk (complete with roving eyeball) and William Shatner are legendary. In your opinion, PopWatchers, what’s been your favorite best celeb-on-celeb impression? The more obscure, the better.