Captain Blood
As recommended by OhRomeo and cheveguara
“Wot, no Captain Blood?” asked OhRomeo, while cheveguara states that Captain Blood is “one of the great pirate films”. Errol Flynn portrayed him in the 1935 film adaptation of Rafael Sabatini’s novel. To escape a life of enslavement, Blood, once an esteemed doctor, turns to piracy to reclaim his freedom.
Captain Levasseur
As recommended by Aireman and NuitsdeYoung
Captain Blood’s biggest foe was the treacherous Captain Lavasseur, played by Basil Rathbone. Lavasseur harboured a desire to kidnap Blood and his crew, and intended to exchange them for a ransom. A duel ensues between the two rivals, with Lavasseur suffering fatal wounds. NuitsdeYoung determines that Rathbone was “actually far superior to Flynn as a fencer, and should have won had they been fighting for real”.
Grace O’Malley
As recommended by pconl, Rosdubh5 and Celtiberico
Upon her father’s death in the late 16th century, Grace O’Malley was set to inherit his shipping and trading businesses. Alongside these valuable assets, O’Malley - often referred to as Granuaile – also earned the trust of a fleet of seafaring men. Owing to unsettled Anglo-Irish relations, O’Malley was sometimes accused of piracy. Her reputation lives on to this day, with Celtiberico suggesting, “Granuaile merits a mention”.
Captain Slaughterboard
As recommended by MrWestons and Adamasto
British author and illustrator Mervyn Peake first introduced his tales of Captain Slaughterboard to the public through Country Life in 1939. We meet the once swashbuckling Slaughterboard in the latter half of his life. His crew on board the Black Tiger desert him, leaving him free to spend his final years of life fishing with “The Yellow Creature”.
Samuel ‘Black Sam’ Bellamy
As recommended by BearsandPears
Samuel Bellamy, later known as ‘Black Sam’ owing to his refusal to conform to the powdered wigs of the late 18th century, enjoyed an extremely brief yet prosperous career as a pirate. Bellamy’s short-lived life of crime equated to riches totalling the equivalent of £83m today, and it is claimed he commandeered at least 53 ships. Dying in a storm at the tender age of 28, Bellamy’s reputation of being the most profitable pirate in history lives on to this day.
Captain Dan Tempest
As recommended by Fallowfield and PoppaAlcohol
“The Buccaneers!!!! God, that was good,” recounts reader PoppaAlcohol of the 1956 TV series. In a show aimed at children, Robert Shaw played the part of re-formed pirate-turned-good, Captain Dan Tempest and his crew aboard The Sultana. Following Tempest on his adventures in and around Nassau, the series was set in the early 1700s and was one of the first pirate-themed television dramas.
Captain Barbossa
As recommended by readers: MisterGrumps and ChrisAlmighty
According to reader ChrisAlmighty, ‘Captain Hector Barbossa was a better pirate than Jack Sparrow’. A fictional pirate featuring prominently in all four of the Pirates of the Caribbean films, Barbossa was reportedly inspired by Hayreddin Barbarossa, an Ottoman naval captain operating in the 1500s. Barbossa is pitted against Jack Sparrow, becoming the archetypal antihero until an outside threat forces the two enemies together in the fourth film, On Stranger Tides.
Richard Worley
As recommended by SpeckledJim1
Richard Worley, a fearless pirate living in the early 1700s, is reputed to be one of the first to fly the Jolly Roger flag. On account of this speculation, SpeckledJim1 decrees “he must be the greatest”. The skull-and-crossbones flag became synonymous with piracy, and Worley was eventually killed because of his profession.
The Pyrates
As recommended by bailliegillies, triggerfish999
“Of course there are many fictional pirates, but if you haven’t already done so, George MacDonald Fraser’s The Pyrates is worth checking out, d’ye see,” suggests reader trigerfish999. Published in 1983, The Pyrates, a comic novel containing a vast array of characters, was adapted for the stage by Chicago’s Defiant Theatre in 2004.
Guybrush Threepwood and LeChuck
As recommended by Ben Mitchell, Temuchin, alanderangle, and lorcanmurray
Monkey Island, a computer game created by LucasArts in the early 1990s, plays host to pirate protagonist Guybrush Threepwood. The second game in the Monkey Island series, The Secret of Monkey Island, introduces the player to evil villain LeChuck. Reader lorcanmurray claims: “Clearly the greatest pirates were either Guybrush Threepwood or LeChuck.”