Jokes at Matt Damon's expense have been a long-running gag on Jimmy Kimmel Live (witness the host's customary sign-off), so perhaps it's no surprise the Oscar-winning screenwriter and Bourne Identity actor would so readily agree to appear in this skit a hysterical, profane, absurdly specific confession of infidelity by Kimmel's girlfriend, comedian Sarah Silverman. It's an exuberant send-up of music video clichés, from butterfly-strewn back-up dancers to corny pillowfights and hip-hop showdowns, with an unavoidable Good Will Hunting pun thrown in ("Hey Kimmel, how do you like these apples?"). Kimmel fired back with his own, possibly even more outrageous love anthem to Damon's friend Ben Affleck, but the laughter died down considerably in July when Silverman and Kimmel announced the end of their five-year relationship. Accepting an Emmy for the sketch in September, Silverman jokingly dedicated the award to "the person for whom this was made, Jimmy Kimmel, who broke my heart...oops...I mean, who will always have a place in my heart." Silverman still drops by her ex's show from time to time, with predictably awkward results.
Next Tina Plays Palin