Jack O'Lantern

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Jack O'Lantern was the antagonist in the Halloween special, Billy & Mandy's Jacked-Up Halloween.

According to Grim, Jack was a prankster in medieval Endsville, which is presumed to be between the 1500-1600s. He was pleasant, but he loved to pull pranks on the townspeople (sawing chair legs, changing road signs, "kick me" signs, etc). He is also shown to have (presumably) invented a couple pranks and gags too (such as chattery teeth). The problem with his pranking was that he never knew when to stop, sometimes pulling several pranks in a row on the same person, and occasionally pulling pranks that resulted in someone getting hurt. Jack was obsessed with inventing new tricks to pull on the people, staying up creating various prank devices, then "laughing himself to sleep" when he was finally done.

The townspeople grew sick and tired of Jack's behavior, and all met together to "teach Jack a lesson once and for all". They accomplished this by sending their humorless queen a prank gift and framing Jack for it, knowing that The Queen would punish him. Furious, she immediately sent a knight to his house to execute Jack for the harmless prank.

When Grim came to reap his soul, the prankster refused to go. Jack managed to steal Grim's scythe (by tickling him into dropping it), and struck a deal with him; he would return the scythe in exchange for immortality, so he could keep playing pranks forever. Grim had no choice but to grant Jack his request and made Jack immortal.

Unfortunately for Jack, this enraged Grim (who doesn't like being tricked) and so he decided that Jack would not show his face around town again - ever. And he sliced off Jack's head, resulting in him needing to replace it with a pumpkin, causing him to be shunned by society and forcing him to only be able to play his pranks on Halloween, when he could fit in with the ghouls and costumed people. This slowly caused him to become bitter towards Endsville and society, but most of all, towards Grim.

Before he managed to start his yearly pranks in Billy & Mandy's Jacked-Up Halloween, Billy arrived at his door with Grim's scythe. After discovering that the scythe belonged to the Grim Reaper, he tricked Billy by using a feather to tickle him, stole the scythe, and then used it to possess pumpkins with spirits and cause chaos and destruction to all of Endsville with the goal of taking over the universe and making it Halloween every day, much to Billy's delight. Eventually, Jack began to feel something was missing, and decided to complete his revenge, he needed to chop off Grim's head, as "any head cut off with the scythe stays off forever."

Billy enlists the help of Mandy to save Grim, and Mandy sets up several pranks, only for them to discover Jack was aware of what was going on the whole time. However, Irwin accidentally defeated him by running into all of the pranks Mandy set up, causing his pumpkin minions to laugh themselves to death (literally).

After Jack was defeated, Grim sent him to the underworld. There, he was beaten up by many humorless demons for pulling a prank on them, and it is heavily implied that his pumpkin head was smashed.