24. Pete Doherty
Pete Doherty is one of those guys who is more famous for banging supermodels and bumping coke than his actual career. That doesn't mean that we can't consider the Libertines front man a pioneer of drifter fashion. Doherty also has one of the best lines ever in his Wikipedia article, "Many of his vintage guitars and amplifers have been destroyed in various domestic incidents." Cheers Pete!