Despite what some cartoons and amusement park rides may have led you to believe, pirates were generally not a charming lot. They pillaged, they invaded, and they obeyed only the sea laws they made up as they went along. For proof, check out these 11 real ocean marauders and the waters they terrorized. 

1. BLACKBEARD 

While he would later settle into a kind of catch-all pirate cliché, Edward Teach’s actual exploits were nothing to sneeze at. Fond of arming himself to the teeth, he customized a stolen French ship in 1717 to include 40 cannons and then used it to threaten the port of Charleston, South Carolina, refusing to move until his extortion demands were met. He wasn’t above petty larceny, either: When a man refused to hand over his ring, he took both the jewelry and the finger. It took the British Navy to finally bring him down.   

2. CHARLES VANE 

Vane steered his ship Ranger into lots of trouble in the early 1700s—enough to grab the attention of newly appointed Royal Governor Woodes Rogers in New Providence. After Vane snubbed Rogers’s offer of a pardon, the two forces engaged in what amounted to an oceanic dogfight. Vane set one of his own ships on fire and aimed it at his enemies. As Woodes’s forces frantically steered out of its path, Vane sailed around them to freedom.  His cunning didn’t last, though: Captured in the 1720s, he was hung for his crimes.

3. ANNE BONNY AND MARY READ 

While many women occupied ships of all kinds during piracy’s “golden era” of the 1600s and 1700s, they were normally relegated to servant’s work. Anne Bonny, however, didn’t subscribe to gender roles: When one man complained of her presence, she stabbed him. Legend says Bonny met Mary Read after Bonny’s ship (captained by her lover, John Rackam) had seized Mary’s; the two became close, fighting together as Bonny’s pirate crew stormed fishing boats. When their ship was taken over by Jamaican forces in 1720, the men hid below deck while the women stood their ground. Sentenced to hang, they got stays of execution after it was found both were pregnant. 

4. “BLACK” BART ROBERTS 

After the Welsh pirate Howell Davis seized his African slave ship, Roberts had an understandable distaste for the pirate life—but when Davis was killed, Roberts had no problem taking his spot at the helm. He soon became one of the most successful (or feared, depending on your vantage point) buccaneers of piracy’s golden age. In one instance, Roberts pretended to be part of a Brazilian fleet so he could get close enough to pillage its richest ship. Roberts’s disposition was occasionally challenged by his crew, to which Roberts would typically answer by murdering them. Roberts was ultimately killed by the British Navy in 1722. 

5. EDWARD LOW 

Any pretense of British-born pirates being slightly more humane than their counterparts was abandoned as stories of Edward Low began to spread in the early 1700s. Sailing along North America and the Caribbean, Low seemed to enjoy tormenting his captured and frightened crew. His sadism grew nearly intolerable, but the final straw came when he abandoned his sister ship and all her crew to a British vessel that he could have defeated. His crew eventually abandoned him, and some accounts say he hanged in France, while others say he escaped with his life to Brazil. 

6. FRANCOIS L’OLONNAIS 

While many pirates had a reputation for brutality, L’Olonnais was in a (violent) class by himself. Terrorizing the Caribbean seas in the 1600s, he was fond of dismembering foes—in one instance, even taking a bite of a man’s heart. Some historians believe L’Olonnais was himself eaten by cannibals. 

7. CLAAS COMPAEN 

Dutch pirate Compaen achieved folk hero status for his maritime exploits. As many as 350 ships were victimized by his aggression, and it’s believed that Compaen protected his bounty by bribing authorities in exchange for safe harbor. Even after Compaen had hung up his captain’s hat and settled in Holland, parents would sometimes caution their children to behave—or else they’d call Compaen, their boogeyman, to come after them. 

8. CHENG I SAO 

Also known as Ching Shih, the Chinese widow took over her husband’s impressive fleet of pirate ships in the early 1800s. But her rule came with conditions: no female captive could be harmed; pirates were allowed to purchase the prettiest captives as wives, but if the pirates cheated, they’d be put to death; privateers who didn’t show up for work or deserted the fleet had their ears removed. She later ran a gambling house.

9. SAM BELLAMY 

It’s not often that love makes a man turn to a life of pirate crime, but Sam Bellamy was no ordinary looter: Cape Cod lore says that after being rejected by the parents of his love, Maria, for being too poor, Bellamy took to the seas to find his fortune. He even came close to some kind of righteous reprisal, capturing a slave ship along with all of its gold and silver. No lifetime criminal, Bellamy had gathered enough booty to steer home in 1717—and was promptly caught in a storm that killed him before he could prove his worth. Part of the wreckage was discovered in the latter part of the 20th century, making it the first pirate ship from piracy’s golden age ever recovered in North America. 

10. CHARLES GIBBS 

Originally a member of the U.S. Navy, Gibbs was active during the last wave of pirates in the early 1800s. Once he was captured and standing trial, Gibbs’s practice of killing most of his seized shipmen ignited debate over capital punishment: He murdered most witnesses, he said, since murder and piracy both carried the same punishment (death) and also because “dead men tell no tales.” He was hanged for his crimes in 1831 at Ellis Island. 

11. HENRY AVERY 

Avery, whose cruelty was considered excessive even by pirate standards, stormed the Atlantic and Indian Oceans in the late 1600s. When the volume of gold and silver on board an Indian treasure boat Avery captured while sailing back from Arabia wasn’t enough to satisfy his appetite, Avery is said to have ordered his men to torture passengers to make sure no valuables were hidden. Satisfied he had squeezed them for every ounce, their bodies were thrown overboard. Avery was last seen with a horde of money, but whether he was able to spend it without being identified—making him one of the few pirates to retire in comfort—is lost to history.