6. Zipper Malfunction – There’s Something About Mary (1998)

Awkward movie scenes that made us uncomfortable - Ben Stiller in There's Something About Mary (1998)

There’s Something About Mary opens with a scene explaining why protagonist Ted never ended up with the girl of his dreams. While preparing to take her to prom, Ted visited her family bathroom. Once he had finished answering the call of nature, Ted zipped up his fly, only to trap his private parts inside the zipper. Ouch.

What follows is one of the most awkward and embarrassing scenes in comedy movie history. Ted is subjected to an array of strangers questioning him about his injury, with several of them also taking a good look at his nethers. To top it all off, Ted misses his prom, and doesn’t get to dance with the girl of his dreams.

In all honesty, this one is made all the more awkward by Ben Stiller’s excellent performance as a teenaged Ted. The braces, the hair, the ill-fitting tux – it all contributes to a perfect picture of adolescent embarrassment. The mangled testicle is just a bonus.