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 12 real ocean marauders and the waters they terrorized.

1. Blackbeard

Edward “Blackbeard” Teach’s 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 extortionate demands were met. He wasn’t above petty larceny, either: When a man refused to hand over his ring, Blackbeard took the jewelry and the finger. It took the British Navy to finally bring him down.

2. Charles Vane

Charles 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 in the Bahamas. 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 hanged for his crimes.

3. Anne Bonny and 4. Mary Read

Anne Bonny didn’t subscribe to gender roles. When one man complained of her presence on a ship—thought to be an unlucky omen—she stabbed him. Legend says Bonny met Mary Read after Bonny’s ship (captained by her paramour, “Calico Jack” 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. After being sentenced to hang, they got stays of execution after it was found both were pregnant.

5. “Black” Bart Roberts

Welsh pirate Bartholomew Roberts was 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.

6. 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 crews. His sadism grew intolerable, and the final straw came when he abandoned his sister ship and all its crew to a British vessel that he could have defeated. His crew eventually abandoned him, and some accounts say he was hanged in France, while others say he escaped with his life to Brazil.

7. François L’Olonnais

While many pirates had a reputation for brutality, L’Olonnais was in a (violent) class by himself. He terrorized the Caribbean in the 1600s and 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.

8. Claes Gerritszoon 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 European 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.

9. Zheng Yi 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 leadership 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. Zheng Yi Sao later ran a gambling house.

10. “Black 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 poor, Bellamy took to the seas to find his fortune. He ended up capturing the Whydah, a ship stuffed with gold and silver after it had delivered its cargo of enslaved Africans to the Caribbean. 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 of the Whydah 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.

11. Charles Gibbs

Rhode Island-born Charles Gibbs was active during the last wave of piracy in the early 1800s. Once he was captured and standing trial, Gibbs’s practice of killing most of his seized ship’s crews 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.

12. Henry Avery

Henry Avery (also known as John Every), whose cruelty was considered excessive even by pirate standards, stormed the Atlantic and Indian oceans in the late 1600s. His greed was legendary: When the volume of gold and silver on board the Indian treasure ship Ganj-i-Sawai wasn’t enough to satisfy his appetite, Avery is said to have ordered his men to torture passengers to make sure no more valuables were hidden. When he was satisfied he had squeezed them for every ounce, he threw their bodies overboard. Avery was last seen with a hoard of money, but how he was able to spend it without being identified is lost to history.

A version of this story was published in 2015; it has been updated for 2023.

This article was originally published on www.mentalfloss.com as 12 of the Fiercest Real-Life Pirates in History.