A list of real-life historical pirates. When the word pirate is mentioned, images of Johnny Depp as Captain Jack Sparrow instantly come to mind. Real pirates, however, were (and are) a lot more intimidating. These marauders and swashbucklers have roamed the seas for hundreds of years, raining terror and mayhem down on poor unsuspecting souls. These are the most successful and/or terrifying pirates to ever sail the ocean blue.Who is the most successful pirate? This list of real life pirates will befuddle, maybe even bewilder you, knowing that these men of the high seas actually pulled off heists worthy of the movies.