Halloween is a storyline mission that occurs in Chapter 1.
The Mission[]
Intro[]
Gary, wearing the uniform of an SS officer, meets Jimmy in his dorm room, providing Jimmy with a skeleton suit. They meet Pete, who's been given a pink bunny costume by Gary, and head out of the dorm for a night of pranking. 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, and so there aren't any authority figures to get in the way of a night of "fun."
Walkthrough[]
Russell is in the dorm hallways and Jimmy must either fight or run from him. He won't follow Jimmy outside the dorm. Once outside, Jimmy must complete errands that other students assign him.
- 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.
Once five of the six errands are completed, The Big Prank begins.
Gary and Pete follow Jimmy throughout the mission. If Gary gets knocked out the mission is failed, but if Pete gets knocked out only the opening cutscene of The Big Prank is changed.
Collectibles[]
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 (2/3 full).
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.
List of Students in Costumes[]
- Jimmy: Skeleton
- Gary: Waffen-SS officer
- Pete: 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[]
- 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 Greasers are unusually aggressive during this mission. Although the game never prompts the player to go to the Auto Shop, should they go there, the Greasers attack on sight. They also respawn more quickly than usual.
- The music that plays during this mission was originally used in the PlayStation 2 game, The Getaway. Shawn Lee composed the soundtrack for both games.
- The werewolf mask can be obtained by picking a locker during or after this mission.
- While wearing the costume, the other students will make fun of Jimmy and will insult him about his costume. This doesn't happen to other students.
- Pete's costume might be a reference to the movie A Christmas Story, as main character Ralphie Parker wears one similar to his at a certain point in the movie. In Ralphie's case, an aunt made it for him and his mother forced him to wear it.
- Jimmy's skeleton costume could be a reference to The Karate Kid movie. In that movie, protagonist Daniel LaRusso is bullied by students of the Cobra Kai dojo. During Halloween, the Cobra Kais wear skeleton costumes similar to Jimmy's.
Deleted/altered content[]
- 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.
- Pete being the only one punished for the pranks when he was being dragged along and didn't want to be there was an ongoing joke; it's quite possible the mission was redesigned because this was too mean-spirited to be enjoyable to many players.
- At one point in development, Gary was going to have a Nazi swastika on his outfit. This was changed due to controversy and the possibility of Germany banning the game entirely due to their laws forbidding Nazi symbolism. More information on this can be found here.
"Endless Halloween" glitch[]
- It is possible to make Halloween last indefinitely. Jimmy must get busted on Halloween night between the hours of 1:30 and 1:59 a.m.. He will wind up in the Principal's office, at 8:00 a.m. the next day, 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 a.m.. It will end by going to bed or passing out at 2:00 a.m..