- "Load your guns with chain shot! Aim for their rigging -- we must slow them down!"
- ―Jack Sparrow
Chain-shot were a type of ammunition formed of two iron sub-calibre balls, or half-balls, chained together. They were used in naval warfare to shoot down yards, masts, or to cut the shrouds, or any other rigging of a ship.
The chain shot was invented in the 1600s. It consisted of two cannonballs or half-cannonballs joined by a chain; fired at an enemy ship to destroy its rigging. After leaving the muzzle, they would tumble in the air. This caused the chain shot to fully extend. As much as six feet of chain would sweep through the target. However, the tumbling made both bar and chain shot less accurate, so they were used at shorter ranges.
Chain shot was the most common shot used to damage a hostile ship's masts and rigging. It was, however, not a shot to be fired over very long distances. Its cousin: bar shot (full or half balls held together with a fairly long bar) could go over a hundred yards farther, although not doing as much damage. The most damaging de-masting shot is the star-shot, tearing through all rigging and sails, but used at very close range.
The cursed crew of the Black Pearl was known to employ chain-shot during battle. Pintel and Ragetti toppled the mast of the commandeered the Interceptor with chain-shot, rendering it dead in the water and trapping William Turner below decks. Captain Jack Sparrow's crew later used chain-shot against the cursed crew to knock the pirates overboard, allowing Sparrow to plunder their ship. Clanker from the Flying Dutchman had chain shot as a weapon.  At the end of the battle around Calypso's maelstrom, the crew of the Pearl used a chain-shot to free their mast from the Flying Dutchman's mast.
- Pirates of the Caribbean: The Curse of the Black Pearl (First appearance)
- Pirates of the Caribbean: Dead Man's Chest
- Chain Reaction!
- Pirates of the Caribbean: At World's End