Bringing Up Baby (1938)
This film is the meet-cute to end all meet-cutes. It's one of the earliest renditions of a screwball comedy and paves the way for other directors to follow in its footsteps. Cary Grant portrays a paleontologist who falls for heiress Katharine Hepburn the night before his marriage to another woman. The wacky events that ensue are unrealistic and hilarious.
Pretty Woman (1990)
This was originally going to be a dark indie drama about evil Hollywood, but it turned into something very different. Julia Roberts was the perfect match to play a woman who was introduced into the world of the wealthy. One cool fact about the film is that many of the best parts were improved. Julia Roberts is a natural!