- Photo: Paramount Pictures/Promotional5 of 14
These days he's playing opposite Charlie Sheen (another Hughes fave) in the smash-hit "Odd Couple"-esque show "Two and a Half Men," but long before his sitcom days he was none other than Duckie, the awkward but lovable best friend to Molly Ringwald in "Pretty in Pink." Totally smitten by Andie (Ringwald), Duckie pulls any stunt he can to get her to notice him for what he is: completely and utterly hers. This is one of Hughes' few nerdy characters that DOESN'T get the girl in the end... well, not Ringwald. He DOES get Kristy Swanson, the original "Buffy the Vampire Slayer" and Simone in "Ferris Bueller's Day Off." Also, you can rest your worried mind knowing that Duckie finally got the girl in real life when he married hottie Lisa Joyner, and now lives in blissful, syndicated heaven.