2. There's Something About Mary (1998)
Any delusions of getting some on prom night are dashed the moment Ted Stroehmann (Ben Stiller) jams his junk in his zipper in the bathroom of dream girl Mary Jensen's (Cameron Diaz) house. To make matters worse, Mary's stepdad (Keith David) takes it upon himself to try and remedy the situation, only to question, "How'd you get the beans above the frank?"
All of the neighborhood watches on as an ambulance ride to the hospital replaces a limo to the big dance for Ted.
To reiterate, Ted caught his penis and scrotum in the teeth of a zipper.