Halloween

Halloween is a storyline mission that occurs in Chapter 1.

The mission
Gary, wearing the uniform of a Nazi SS officer, meets Jimmy in his dorm room, providing Jimmy with a skeleton suit. They meet Petey, who's been given a pink bunny costume by Gary, and head out of the dorm for a night of pranking, having to avoid Russell. As Gary explains, the Prefects are busy at a party and the Teachers are supposedly entertaining the kids, but are really holed up in the lounge.

Jimmy can run several errands that involve throwing stink bombs, itching powder and eggs at students, tripping students with marbles, and setting off a Volcano 4000 firework. Gary and Petey follow him the whole mission, unless they are knocked out.

Completing 5 of the 6 errands unlocks The Big Prank.

Individual Missions

 * Pedro asks Jimmy to tag someone with a "Kick Me" sign.
 * Casey asks Jimmy to throw eggs at students.
 * Lucky asks Jimmy to trip someone with marbles.
 * Fatty asks Jimmy to throw stink bombs.
 * Donald asks Jimmy to set off a Volcano 4000 firework.
 * Parker asks Jimmy to throw itching powder.

Tombstones
The tombstones appear immediately after The Candidate ends, but before Halloween actually starts. As the clock disappears after The Candidate, Jimmy has plenty of time to look for them.

If Jimmy has not smashed all the tombstones by the end of The Big Prank, he can find them inside the Spencer Shipping Warehouse during Chapters 5 and 6.

Smashing all of them earns him a trophy for his room, and the Edna Mask that Troy wears during Halloween.

Pumpkins
During Halloween, there are jack-o-lanterns placed all around campus. If Jimmy destroys all of them, he earns the pumpkin mask that Lucky wears, and a trophy for his room.

If Jimmy doesn't destroy the pumpkins, they will appear in the school basement and can be destroyed during or any time after Help Gary.

The best time to search and destroy the jack-o-lanterns is during Halloween. Although they're still available during and after The Big Prank, the clock is absent during Halloween, giving him unlimited time to find them all.

As there are no teachers and prefects around, this is a good night to break into lockers and steal items, although they will return if the player's trouble meter goes beyond level 4 (2/3rds full).

Students in costumes

 * Jimmy: Skeleton
 * Gary: Nazi SS officer
 * Petey: Pink bunny
 * Angie: Witch
 * Gordon: Hockey mask
 * Pedro: Mummy
 * Trevor: Werewolf
 * Troy: Edna mask
 * Donald: Alien
 * Fatty: Wizard
 * Thad: "Super-Thad"
 * Parker: Vampire
 * Pinky: Princess
 * Lucky: Pumpkin head
 * Vance: Pirate
 * Casey: Demon mask
 * Damon: Astronaut

Trivia

 * Originally, Gary was going to hand out all the individual mini-missions to Jimmy. He also was going to order Jimmy to prank Eunice with a dead rat. There was also a part including Mr. Burton and Dr. Slawter mocking Pete for his costume and subsequently getting pranked with itching powder.
 * Vance acts like a non-clique student in his costume and can be seen talking to them instead of the Greasers. Sometimes he even gets into fights with his fellow Greasers during this mission. Trevor will act like a Bully; he uses the same fighting style that they use, he will also taunt and shove Jimmy if he greets him.
 * The music that plays on this mission was originally used on the PS2 videogame The Getaway. Shawn Lee composed the soundtrack for both games.
 * Picking a locker after this mission earns you the werewolf mask.

"Endless Halloween" glitch
It is possible to make Halloween last indefinitely. All Jimmy needs to do is get "busted" on Halloween night, between the hours of 1:30 and 2:00 AM. He will wind up in the principal's office, at 8:00 the next day, and all of the students will still be in their costumes. Further, if Jimmy did not do the Big Prank, the prefects will remain absent, allowing Jimmy to ditch class, fight other boys, and break into lockers with impunity. This "endless Halloween" will continue as long as Jimmy keeps getting himself busted after 1:30. It will end by going to bed or passing out at 2:00.