The Pirate King (Kevin Kline), The Pirates of Penzance (1983), He sings, he dances, he makes us laugh. Kline warms up for A Fish Called Wanda (1988).
The Dread Pirate Roberts (Cary Elwes), The Princess Bride (1987), Granted we never get to see the Dread Pirate engaged in the nefarious acts that earned him his moniker, but clearly after besting the Spaniard, the Giant, the Sicilian, and Prince Humperdink, he proves himself to be a paragon worthy of any princess this side of Guilder.
Han Solo (Harrison Ford), Star Wars (1977), Set the stage for all interstellar scruffy-looking nerfherders to follow.
Sir Walter Raleigh (Clive Owen), Elizabeth II: The Golden Age (2007), Clive Owen is clearly living out a boyhood fantasy as he cheerfully smiles his way through every smouldering scene.
Errol Fynn, more familiar with his work in the Robin Hood series, Flynn brought the same sense of acrobatic dynamism and physicality to many of the pirate movies he made. Top on our list of Flynn pirate movies to watch is 1952's Against All Flags, but we're willing to bet that 1940's The Sea Hawk set the standard.
Gene Kelly, Serafin/Fake Macoco, The Pirate (1948), It's hard to decide who came first. When Serafin, an actor, decides to impersonate the legendary pirate Macoco, the pirate he creates is based on character types clearly established by Flynn in his earlier films. Kelly's Serafin-as-Macoco is an inspiration for Kline's Pirate King, as well as contributing to the device that William Goldman uses to establish the Dread Pirate Roberts.
Walter Slezak, Don Pedro Vargas/Macoco, The Pirate (1948) For my money, Macoco is one of the best pirates going for several reasons. First, Macoco is at the top of the pirating world when we meet him, having successfully "retired" from his corsairing life. As with many outlaws and bandits, surviving into old age is the only real measure of success, but for Macoco old age and respectability prove elusive. Unlike a lot of current action films where the bad guys are all bad all the time, or ultimately redeemed, Macoco carries an element of hubris around him as heavy as immense bulk. Macoco wants to put his past behind, but he can never successfully bury the greed and anger that made him the scourge of the Caribbean, allowing Serafin to trick him into revealing himself in a fit of rage.
