6. Guybrush Threepwood
Long before Guybrush Ulysses Threepwood ever became a pirate, he was a scrawny, awkward teenager with naught going for him aside from some pretty sharp wit and the ability to hold his breath underwater for a substantial amount of time. It was odd, then, that his sole ambition was to become a pirate, considering he was woefully ill-equipped with the kind of traits one might associate with buccaneers. On paper, Guybrush was doomed to fail. But luck had other plans for him.
First, he managed to win the heart of the lovely Elaine Marley, governor of Melee Island, who, despite Guybrush's faults, was attracted to his personality and wit. Then there's the whole matter of his battle with the ghost pirate LeChuck, who effortlessly dominated Guybrush--that is, until Guybrush sprayed him with a bottle of root beer out of desperation. As luck would have it, ghosts are apparently very allergic to root beer. By sheer chance, Guybrush's exploits defeated the feared pirate ghost, earning him a reputation as a pirate himself--even though his physical and mental traits didn't really do him any favors.