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Jester

Location Castles
HP 1
Notes Will sometimes steal your highest-tier unequipped weapon when adjacent; drops the key to a random prison cell
Killing the Jester gets you a key to one of the castle prison cells, but it also makes the Guards attack you. Whether you get the key to the Princess's cell is random, and the only way to find out is to try to open it.

The Jester will randomly decide to steal Weapons if you happen to be standing in an adjacent square, much like Bards in towns. The Weapon stolen is the best one in your inventory, though Jesters can't steal the Weapon you have equipped. (They can steal extra copies of it, however.)
Compare Jester to other Creatures
King Princess

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Obtain a Shuttle and become a Space Ace by destroying 20 enemy vessels, locating a Time Machine in the process.

Jester

Location Castles
Notes Will sometimes steal all of your unequipped weapons when adjacent; drops the key to a random prison cell
Killing the Jester gets you a key to one of the castle prison cells, but it also makes the Guards attack you. Whether you get the key to the Princess's cell is random. You can check your inventory to determine which key you got—you want the key to cell #2.

The Jester will randomly decide to steal your Weapons if you happen to be standing in an adjacent square, much like Bards in towns. They will steal all of your reserve Weapons, so try not to give them the chance. If possible, use a ranged Weapon to kill a Jester so you don't have to get near them.

Jester

Appears on This creature does not appear randomly
Jesters generally wander around being annoying, but can almost always be ignored. The notable exception is in New Jester, where a horde of Jesters will try to corner you, forcing you to fight your way out. There's really nothing good that can come of dealing with Jesters anywhere.

Jester

Experience 2
Jesters are weak foes and are rarely aggressive, but they can be annoying so I really can't blame you if you kill a few here and there. Interestingly, the only Jester in the game with a worthwhile hint is the one being tortured in the Castle of Lord British. (Maybe he was being tortured for not being annoying enough?)