Sarah Silverman sings about how she "cheated" on Jimmy Kimmel
In 2008, Matt Damon served as the butt of a running joke in which Jimmy Kimmel would always "run out of time" before their interview segment. Vowing to get his revenge on Kimmel, Damon enlisted the help of Kimmel's then-girlfriend Sarah Silverman.
She and Damon appeared on an episode of Jimmy Kimmel Live! together to confess that she had been cheating on Kimmel with Damon via song. Although Kimmel pretended to laugh along, it was obvious that he was seething inside.