5. Duckie - Pretty In Pink
As naturally charming as Molly Ringwald is, it's hard to argue that her character in Pretty in Pink isn't exactly the most endearing. She's a cute little redhead who's got a thing for a yuppie two or three tax brackets above her. Sure, she's from the wrong side of the tracks and it's not easy being poor, but her father loves her and she's got a wonderful group of friends who would clearly take a bullet for her. So what's with all the teenage angst? For me, this movie begins and ends with Duckie, played to perfection by Jon Cryer. He's a hilarious, frenetic character who's so full of charm and love that it's hard to imagine Andie not falling for him. He's the classic best friend who tries a little too hard, but that doesn't mean that he's not a great person. Plus, as we learn from Annie Potts, he's got strong lips. Which is always a plus. I was heartbroken when they didn't end up together, even if Duckie did get the consolation prize of going to prom with a young Kristy Swanson.