Owen Wilson at the New Mexico Military Institute; Owen Wilson—Today

Every good rom-com needs a bad boy with a heart of gold, and long before he headed out to Hollywood, it seems Owen Wilson was preparing for that part. When he was a teenager, he was expelled from school for cheating on a geometry test and shipped off to a New Mexico military academy, where his surfer blond locks were buzz-cut close to his scalp. But in case you’re wondering if his broken-nose-that-never-quite-healed-right was a result of tactical training gone awry… he insists otherwise.