3. The Truth About Cats and Dogs (Michael Lehmann, 1996)

This is a big reference point for phone sex in film, because it was one of the first times phone sex was treated like legitimate sex on screen. It's also kind of the best moment in the movie. Janeane Garofalo will always be one of my personal favorites, but she's underused here. And it makes me impossibly sad that, in the world of this movie, it's just sort of accepted that she is a hideous troll person, and therefore unworthy of male attention. (Hollywood Ugly: anyone this side of Penelope Cruz.) However! The sex scene in question is totally hot. They're into it! It's a little awkward! They both get off! Hooray!

NEXT: "The phone sex in this movie earned it an NC-17 rating without the deployment of a single boob..."