7. Lloyd Dobler - Say Anything
Cameron Crowe's leading hero in his debut "Say Anything..." is one of the most recognized lovable movie characters out there. His honest attitude and inability to do or say anything insensitive allows him to be the shining underdog of the romantic comedy genre, outrunning even some of John Hughes' best characters. The most famous scene of "Say Anything..." is short, but has become the ultimate romantic gesture, even referenced in the end of Will Gluck's 80s movie grandchild "Easy A". A recent episode of How I Met Your Mother did address the fine line between sweet and crazy with the Dobler/Dahmer distinction, where one's gesture could come off as a testament of strong will and sweet persistence, or as unsettling and possibly murderous. If you take Dobler's actions at face-value though, maybe adding a more ominous score over the film, the distinction could be a bit more blurry. First of all, the guy is a trained fighter who regularly wears a trench coat. His persistent get-the-girl nature is nothing short of adorable in the film, but had Crowe tweaked the tone ever so slightly we would have a problem. I mean, honestly, standing outside of a girl's house with a stereo blaring the song you guys got down to once, that's an interesting choice. Also, revisit the idea of asking your friend to take a picture while you stand in the background of a girl you don't know and her father.