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Played By: Quinn LordA strange young trick-or-treater wearing a flour sack mask and orange pyjamas, Sam appears throughout the film without much purpose. He originally appeared in Michael Dougherty's short "Seasons Greetings". However, it becomes clear there's more to Sam than there appears. He is revealed to be the Spirit of Halloween, laying the law down on those who break the rules of Halloween (wear a costume, give out candy, never extinguish a jack o'lantern before midnight) with killing intent and revealed to be an Improbable Weapon User and a Killer Rabbit. His fight with Mr. Kreeg reveals him to be a pumpkin-headed demon of sorts, hence why he wears the mask.
Main Characters in "The Principal"
Principal Steven Wilkins
Played By: Dylan BakerA seemingly innocent school principal who loves Halloween, Steven Wilkins actually hates those who disrespect the customs of Halloween and kills those who break the rules. He has a son, Billy, who appears to be molding into his Daddy's Little Villain. He later moonlights as a vampire-like man wearing a hooded cloak, and stalks Laurie. Unfortunately, this doesn't go well when Laurie is revealed to be a werewolf wanting her first kill, and Steven is the unlucky victim.
Played By: Connor Christopher LevinsBilly is Steven's loud, but beloved child who loves spending time with his father, particularly on Halloween. He is very enthusiable about carving the jack o'lantern, actually Charlie's severed head. He also considers Charlie Brown to be an asshole.
Played By: Brett KellyA Fat Bastard kid who uses Halloween to cause mischief and steal candy, even though he's diabetic. His attempt to steal candy from Steven's porch results in Steven poisoning him. His head is then removed and used as a jack o'lantern.
Main Characters in "The School Bus Massacre Revisited"
Played By: Britt McKillip
Played By: Jean-Luc Bilodeau
Played By: Isabelle Deluce
Played By: Alberto Ghisi
Played By: Samm Todd
The School Bus KidsEight disturbed children who were sent to their watery deaths thirty years ago. They are brought back from the dead by Sam to exact their Ghostly Goals on Halloween.
Main Characters in "Surprise Party"
Played By: Anna PaquinA young, pretty girl Laurie wishes to spend this Halloween trying to have her "first time". She's accompanied by her older sister Danielle, and two other friends, who are all going to a party together. She spends much of the film wandering around dressed as Little Red Riding Hood until she attacked by a vampire, actually Steven. However, she turns the tables on him and reveals she is in fact a werewolf and her first time is actually killing and eating her date.
Played By: Lauren Lee Smith
Played By: Rochelle Aytes
Played By: Moneca Delain
Main Characters in "Meet Sam"
Played By: Brian CoxSteven's neighbour, an aging Jerk Ass recluse with a Dark and Troubled Past. He has an Angry Guard Dog named Spite (seriously), and arms himself with a shotgun if there's trouble. In the film, Mr. Kreeg hates Halloween and gets an unwelcome visit from Sam, resulting into a Hopeless Boss Fight with the supernatural child. It is revealed that he is the bus driver who planned on driving eight insane children to their deaths thirty or so years ago, being the only survivor after the school bus the kids were on was accidentally driven into a lake by one of the scared children. Mr. Kreeg survives his encounter with Sam, but is later visited by the undead bus children who kill him.
Emma and Henry
Played By: Leslie Bibb & Tahmoh PenikettA loving couple who have an unpleasant Halloween with their various run-ins with the other characters, plus Emma wearing a bulky robot costume. Returning home, Henry runs inside to watch a sex tape whilst Emma clears up the Halloween decorations before midnight, resulting in Sam paying her a visit and killing her by slashing her throat with a broken lollipop.
Shadow ManA mysterious man shrouded in darkness who stalks Sam in the short Season's Greetings. He follows Sam into an alley way, and appears to beat him up. That is until Sam emerges carrying the man in his sack. Does not appear in the film proper, but is featured in the Season's Greetings short.