The Most Iconic (and Cringeworthy) Moments in Talk Show History

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.

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Post originally appeared on Upbeat News.