Remember back when Patrick Dempsey was a scrawny little nerd who was so lame that he had to resort to paying a cheerleader $1000 to pretend to be his girlfriend? Don't feel bad, most people don't. But before he grew into his looks and became McDreamy on Grey's Anatomy, he starred in the underappreciated 80s classic Can't Buy Me Love. He personifies the wistful geek who just wants to not be invisible for once in his life. But in my opinion, the film is made by the appearance of a young Seth Green, who plays Dempsey's fantastically obnoxious prepubescent brother. For my money, this film is the gold standard of the geek-to-chic movie trope. Word to the wise, though: this film does feature some of the most heinous 80s fashion I've ever seen in my life. So don't say I didn't warn you.