10. Mr. Levenstein (Eugene Levy) and Jim (Jason Biggs) in American Pie
American Pie was a movie about four high school seniors who make a pact to lose their virginity by prom night. As Jim tries to figure out how to get foreign-exchange student Nadia into bed with him, his father gives him hilarious and awkward advice along the way. The most hilarious exchange between father and son during the movie is when Mr. Levenstein brings Jim a stack of pornography magazines and gives him a tutorial on them, while also trying to figure out more modern sexual expressions. Considering this comes shortly after the movie’s opening scene where he and his wife walk in on Jim masturbating into a sock, it’s his strange way of showing his son he loves him, and only wants him to do things in a healthier way, evidenced by his closing line in the scene as he opens Jim’s nightstand drawer to find condoms, picks them up, and quips, “Well, it’s safer than a tube sock.”
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