Johnny Depp as Captain Jack Sparrow (2003-present)

Nobody plays a drunken scalawag like Johnny Depp does. A mixture of Keith Richards and a corpse, Depp refined what the definition of a pirate is and did it with style. Although he may be forever doomed to live inside the belly of the Kraken, Captain Sparrow was the dastardly fool with a drinking problem you couldn’t help but love.

Roberto Clemente (1955-1972)

During his time in Major League Baseball, Roberto Clemente was one of the greatest (Pittsburgh) Pirates of all time. Although he may never have made anyone walk the plank, he hit many balls out of the pARRRk. Also, like his sweaty, pillaging pirate family, Clemente was from Puerto Rico, a hotbed of pirate activity for a time.

Dustin Hoffman as Hook (1991)

Reinventing what a pirate should be, Dustin Hoffman became the curly-bearded scoundrel Hook with a mission to stop a little boy in tights. Chrome-ing out his hook way before rappers even had the notion, Hook met his demise in a grand fashion with a bite from a razor-toothed crocodile – like any great pirate should.

Shawn Fanning (1999-2001)

On the forefront of digital piracy, Shawn Fanning’s Napster revolutionized piracy and gave poor college students the opportunity to be their own version of Black Bart. Although the pillaging conquest was eventually taken down by the great Metallica empire, its run is one that kept piracy alive in the modern day.

Captain Morgan (1983-Present)

On the weekends, it’s not surprising to see many people littered along Welch Avenue who have a little Captain in ’em. Giving us many blurry nights and headache-filled days, Captain Morgan spiced rum has become one of the most ubiquitous liquor icons. The best part about this rum, however, is that it’s not filled with impurities and pirate spit.

John Madden (1969-1978)

Known as the lovable oaf who comments on NFL games with a high degree of disorientation, John Madden lived the life of a buccaneer for a good portion of his career. Leading his Oakland Raiders to several successful seasons, Madden never donned an eyepatch but probably would look very fashionable wearing one.

Evan Stone as Captain Edward Reynolds (2005)

Nothing says pirate like a timely quip. Captain Reynolds provided many memorable quotes in “Pirates,” including “Evil doesn’t stand a chance against these twin hellfire cannons.” The highly successful movie was also the biggest budgeted adult film ever. After its comedic plot began to create buzz, the film went on to be cut to an ARRR rating and sold at rental chains.

Cap’n Crunch (1963-present)

Although Cap’n is the “good” sailor of the seas (not to be confused with his nemesis, Jean LaFoote the Barefoot Pirate), there is no question the Cap’n had a dark side. Word is, when the Crunch Berries were introduced to the Cap’n and his crew, he was as ruthless with the little buggers as Davy Jones himself. And don’t even start on the devastation his cereal does to the roof of your mouth.