There’s Something About Mary (1998)

The Farrelly brother’s portrayal of mild-mannered geek Ted Stroehmann is genius as he chases down the woman of his dreams, someone who has eluded him since high school.  Unfortunately, several others are hot on Mary’s heels as well.

Men everywhere sucked in their breath and hugged themselves a little upon seeing the scene where Ted inadvertently zips up his pants the wrong way. As the screams were heard round the world, audiences found themselves both horrified and amused.