50 Mortifying, Awkward, Yet Incredibly Entertaining Moments You’ll Ever See In Talk Show History

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When Sarah Silverman Sang About Her “Cheating” Stint on Jimmy Kimmel

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Jimmy Kimmel had a long-standing joke on his show where he would always “run out of time” before he could bring in Matt Damon for his interview. While it was a joke, Damon claimed that he would take revenge, and boy, that’s exactly what he did. At that time, Kimmel was dating comedian Sarah Silverman so Damon requested for her help. They both came on the show in what was supposed to just be a friendly interview between friends but she ended up singing a song which talks about her “cheating” on Kimmel with Damon. Although Kimmel tried to look okay with it, it was obvious that he wasn’t happy at all.