Sarah Silverman, Jimmy Kimmel Officially F***ing Other People

You know that moment a little bit after you find out that two of your friends have ended their relationship — the moment that follows all the sympathy and condolences, the moment of “oh, crap, they were such a fun couple, and now they won’t be having those awesome BBQs anymore”? That’s the way I feel about Jimmy Kimmel and Sarah Silverman breaking up. Because in the grand tradition of real-life couples Lucy and Desi and George and Gracie, their union created some hilarious comedy. Though perhaps the nature of the pieces was an early warning sign.

Silverman presented I’m F***ing Matt Damon to Kimmel as a gift in honor of Jimmy Kimmel Live’s 5th anniversary (it was originally meant to be aired in November 2007 during Kimmel’s birthday show, which never happened due to the WGA strike), and uploads of the video quickly appeared on YouTube in a Lazy Sunday-esque wave.

The choice of partners is deliberate, as Jimmy Kimmel has a long-standing joke feud with Matt Damon (culminating in a rage-filled appearance in September 2006), but who knew that Matt Damon could not only rap, but bust out some 90s-dance-crew moves?

And who knew that Kimmel would raise the bar so dramatically with a follow-up featuring Damon BFF Ben Affleck? I’m F***ing Ben Affleck may start off like a cheap rip-off, but soon afterwards ups the ante, both in an artistic and cast sense: the quasi-official YouTube upload lists Robin Williams, Don Cheadle, Harrison Ford, Brad Pitt, Cameron Diaz, Christina Applegate, Rebecca Romijn, Benji Madden, Joel Madden, Dicky Barrett, Christopher Mintz-Plasse a.k.a. Mclovin, Lance Bass, Dominic Monaghan, Meatloaf, Pete Wentz, Joan Jett, Huey Lewis, Perry Farrell, Macy Gray and Josh Groban. Sure, there are no butterflies. But there is a “We Are The World”-esque chorus and Harrison Ford in a convertible. Advantage: Kimmel.

Of course, Silverman and Kimmel didn’t work together on these shorts — both were directed by Wayne McClammy, a Jimmy Kimmel Live segment director who’s parlayed his success into exciting directing gigs. But the established nature of their relationship in the public eye is what gives these pieces the additional kick. What makes “I’m F***ing Matt Damon/Ben Affleck” so much fun is that the humor of the pieces reflect that stage in a romance when all the insecurity is gone, when both partners are so comfortable with each other that they can make these sorts of tasteless jokes. Now that they’ve broken up, it’s just a little sad, to think of the people they are now, um, f***ing.

But maybe there’s a chance they got together for one last breakup music video. Everyone knows those are always the best.