7) Matt Damon in EuroTrip (2004)
Do not inform Scotty! The start of the R-rated teenage comedy EuroTrip kicks off with an exciting song, "Scotty Doesn’t Know" (created and performed by Lustra) that describes how the main character Scotty (Scott Mechlowicz) has been completely unaware of his girlfriend Fiona's infidelity. To make things worse: The "singer" is portrayed by a shaved-headed, tattooed Matt Damon, who harshly mocks Scotty about how often he has had Fiona in a submissive position.
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Edited by Apoorva Jujjavarapu