There's Something About Mary (1998)

Ben Stiller stars as Ted Stroehmann in the hilarious, groundbreaking comedy There’s Something About Mary (1998). Flashback to 1985, where an awkward sixteen-year old Ted snags a prom date with dream girl Mary Jensen (Cameron Diaz). Good times, right? Wrong. While getting ready for his big date, Ted accidentally gets his junk stuck in his zipper, forcing him to forgo the big day for an ambulance-driven trip to the emergency room, which makes him the joke of his small town.

Fast forward thirteen years later, Ted still maintains an obsession for Mary, so much so that, on the advice of his buddy Dom (Chris Elliott), he hires Pat (Matt Dillon), a private detective, to track down his lost love. The Internet would’ve killed the plot of this comedy! Pat tracks her down in Miami, where she’s living the good life as an orthopedic surgeon. Of course, Mary’s so hot that she catches the private dick’s eye, causing him to lie about Mary to discourage Ted’s desires, so he can make the move on her.

Undeterred by Pat’s slanderous views of Mary, Ted and Dom head down to the Sunshine State to try and reconnect with Mary. Hilarity, DNA-filled hair gel, and an appearance by NFL legend Brett Favre follows, giving us nothing but a close-up look at Stiller’s prosthetic peen in the infamous zipper scene. Bummer.