There's Something About Mary (1998)

There’s something about There’s Something About Mary (1998) that tickles Mr. Man’s bone.

Flashback to 1985, where an awkward sixteen-year old named Ted Stroehmann (Ben Stiller) 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. As you can guess, this skincident makes him the joke of his small town.

Fast forward thirteen years later. Mary has moved on but Ted still maintains an obsession for her. In fact, his crush is so bad that, on the advice of his buddy Dom “Woogie” Woganowski (Chris Elliott), he hires private detective Pat Healy (Matt Dillon) 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 (as well as another part of his anatomy). As such, he disses Mary to Ted so he can make the move on her instead.

Undeterred by Pat’s slanderous views of Mary, Ted and Dom head down to the Sunshine State to try and reconnect with her on their own. 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.