What are the best celeb-on-celeb impressions?

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.

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  • Anonymous

    It’s every comedian’s go-to, but Kevin Pollack’s Christopher Walken is frightening.

  • Rich

    Once on SNL, Sean Penn did a wicked Robert DeNiro.

  • Ep Sato

    Kevin Spacey once did Christopher Walken trying out for the part of Han Solo. It was not only spot on, but it was also hilarious.
    And Will Farrell’s Sean Connery was great at making fun of Alex Trebek.

  • Chaddogg

    Harry Connick Jr….it was a LONG time ago, but on the Tonight Show he just went off one-night and started doing impressions of Harrison Ford (“I’m looking…for a one-armed man”) and Tommy Lee Jones from the Fugitive, and then did some others…one of the best impressions I’ve ever seen.

  • Carl

    Jay Mohr doing Christopher Walken. Hilarious!

  • kal

    also on snl mick jagger doing keith richards was awesome. with mike meyers doing jagger.

  • Paul U.

    Mario Cantone’s Liza Minnelli impression just about made me fall out of my chair…

  • aramis

    Mine too are SNL related:
    -Justin Timberlake as Ashton Kutcher
    -Sarah Michelle Gellar as Christina Aguilera
    -Christina Aguilera as Samantha from “Sex and the City”
    -John Goodman as Linda Tripp
    -Cheri O’Teri as Barbara Walters
    -Phil Hartman (Me he r.i.p.) as Bill Clinton
    -Ana Gasteyer as Martha Stuart
    -Maya Rudolph as Donatella Versace
    Gosh, I was just thinking about this the other day, and could name a lot more than this. These are the best celeb-on-celeb parodies though…

  • Carrie K.

    I’m agreeing with two previous posters:
    Harry Connick was the first one that came to mind . . . he does great impressions.
    AND, Christina Aquilera as Samantha from Sex and the City . . . She was unbelivable!!! She has this confession . . . “I’m a man!” I fell out the bed in laughter.

  • Anonymous

    how about another memorable Letterman moment: Alec Baldwin impersonating Robert Deniro.

  • Ceballos

    Ben Affleck once imitated Matt Damon in “The Talented Mr. Ripley” on SNL…i wouldn’t exactly say it was “spot on”…but it was hilarious.

  • Bexter

    Anthony Hopkins as Marlon Brando
    Kevins Spacey as Jack Lemmon
    Norm McDonald as Burt Reynolds/Turd Ferguson

  • CG

    Mine is also SNL related: Darrell Hammond as Jesse Jackson reading “Green Eggs and Ham”.

  • JJ

    Jay Mohr’s Christopher Walken is fantastic

  • kcholt68

    Jamie Foxx did a letter perfect Denzel Washington win he won the SAG Award for “Ray”.

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