Sam

A 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.

• All Hallows Eve: What he exists for.
• Awesome Sack: Sam carries a sack around with him which contains candy and weapons.
• Badass
• Beneath the Mask: Sam's face is really a skull-like pumpkin head.
• Beware the Nice Ones: Sam appears to be a regular innocent trick-or-treater. Guess again.
• Ceiling Cling: This proves that Sam's not human.
• Chekhov's Gunman
• Cool Mask
• Creepy Child: Oh hell yeah!
• Cute and Psycho: There is something infantile and childish about the way he behaves (whilst not killing people, anyway)
• Did You Just Have Tea With Cthulhu: Steven, Rhonda and Mr. Kreeg to an extent share this trope with him, Steven and Mr. Kreeg giving him candy whilst Rhonda pretty much worships Samhain (the original form of Halloween.)
• Early-Bird Cameo: Over ten years before the film in the short film Season's Greetings.
• Fingerless Gloves
• Fluffy the Terrible
• Giggling Villain
• Implacable Man
• Improbable Weapon User: Sam carries a sack of candy with him...which he uses as weapons. He attacks Kreeg with a razor blade in a chocolate bar, and then turns a lollipop into bladed weapon which he uses to kill Emma.
• Ironic Nursery Tune: "Give me something good to eat..."
• Kick the Dog: Literally. It's implied he harms Mr. Kreeg's attack dog.
  • Pet the Dog: In some of the FEA Rnet promos but especially the Father's Day short.
• Kids Are Cruel: But only if people break or ignore the rules of Halloween.
• Killer Rabbit: Actually played for laughs in an Easter trailer promoting {{Fear.net's}} future 24 hour marathon of the film.
• Meaningful Name: Sam is actually short for "Samhain", the Celtic god of death and harvest, and the original form of Halloween. Even more meaningful when he is the spirit of Halloween.
• Nigh Invulnerable: He can survive having a bullet blown through his head.
• Psychic Powers
• Room Full of Crazy: Sam decorates Mr. Kreeg's bedroom with a flaming pumpkin, and blood written across the walls and ceilings of the Ironic Nursery Tune.
• Scary Scarecrow: He's dressed like one.
• The Reveal: He's a pumpkin-headed serial killer-like spirit of Halloween.
• The Speechless: Sam doesn't say a word aside from giggling and screaming.
• To the Pain: If someone breaks the rules of Halloween.

Principal Steven Wilkins

A 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.

• Affably Evil: In his everyday Principal guise.
• Asshole Victim
• Chekhov's Gun / Fridge Brilliance: The chocolate bar Steven gives Sam is later used to fight Mr. Kreeg.
• Buried Alive: He buries dead kids in his back yard, and a few who are still alive.
• Deadly Prank: Steven poisons Charlie and acts like it was meant to be a Halloween trick.
• Evil Is Petty
• Family Values Villain: Scolds his son for using the word 'asshole'.
• Four Eyes, Zero Soul
• Ironic Echo: Mr. Kreeg says "Screw you!" to Steven when he wishes him happy Halloween. Steven uses this on Mr. Kreeg later, unaware he is being attacked by Sam.
  • Steven also says to Laurie "My my, what big eyes you have" while he's attacking her. She says those exact words back to him before she eats him.
• Malevolent Masked Man: When he becomes the vampire stalker.
• Meaningful Background Event: Steven can be seen following Laurie around the celebrations for most of the film.
• Mugging the Monster
• Sadist Teacher: Only to those kids who mistreat Halloween. Charlie gets the worst of his wrath.
• Serial Killer
• They Look Just Like Everyone Else: This is Dylan Baker's specialty, really.
• Vampire Bites Suck: Steven does it for sheer fun.
• Villain Protagonist: The scene of him trying to hide the fact that he's burying kids in his backyard feels like a wacky sitcom moment.

Billy Wilkins

Billy 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.

• Cheerful Child: Despite being a lunatic.
• Creepy Child
• Missing Mom: It's implied that his father killed her.
• Like Father, Like Son: Played on when Billy is dressed as his father at the end of the film.
• Offing the Offspring: Steven looks like he is going to kill Billy after being annoyed by him, but actually takes the first stab at Charlie's head.

Charlie

A 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.

• Asshole Victim
• The Bully: He's so hated that Sam flips him off in a deleted scene.
• Fat Bastard
• Off with His Head!
• Vomit Indiscretion Shot: A combo of blood and chocolate is shot down Steven's front porch by Charlie.

Macy

• Alpha Bitch
• Asshole Victim
• Bitch in Sheep's Clothing: She's literally dressed like an angel.
• The Bully
• Deadly Prank: Her prank on Rhonda works too well, causing everyone to briefly worry they may have accidentally killed her. But then... well, see the next trope.
• Karmic Death
• Kids Are Cruel

Schrader

• Asshole Victim
• Hockey Mask and Chainsaw: His costume.
• Deadly Prank
• Honey Trap: A mild, tween version.
• Karmic Death
• Nice Guy: Friendly to Rhonda and seems to genuinely like her, but ultimately, not nice enough.

Sara

• Asshole Victim
• Braces of Orthodontic Overkill
• Deadly Prank
• Karmic Death
• Kids Are Cruel
• The Grays: Her costume

Chip

• Asshole Victim
• Deadly Prank
• Dirty Coward
• Karmic Death
• Kids Are Cruel
• Pirate: His costume

Rhonda

• Ambiguous Disorder: Implied to be Asperger's.
• Blind Without 'Em
• Cute Witch: Her costume.
• Deadly Prank: She's the target.
• Idiot Savant: What the other kids call her, although they don't really have any idea what's 'wrong' with her.
• Strange Girl

The School Bus Kids

Eight 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.

• Abusive Parents: Their parents paid Mr. Kreeg to drown their children so they could be free of their burdens.
• Back from the Dead: Thanks to Macy kicking a jack o'lantern into the lake the bus fell into.
• Bus Full of Innocents
• Children Are Innocent: They were before they died.
• Creepy Child: There are eight undead kids to chose from, and all are wearing their Halloween costumes and desiring flesh.
• Ghostly Goals: To get revenge on those who wronged them, and those who torment other kids who are 'different'.
• Idiot Savant: Implied in the case of at least one of them, who is heard reciting pi in a flashback.
• The Undead
• Undead Child
• We Help The Helpless: A possible interpretation for their murder of Rhonda's tormentors.

Laurie

A 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.

• Big Badass Wolf
• Beware the Quiet Ones
• Fanservice: Anna Paquin dressed as a nursery rhyme character is likely to attract some people...until the Fan Disservice that occurs later in the film.
• Little Red Riding Hood: She dresses as Little Red Riding Hood in the film.
• Our Werewolves Are Different
• The Reveal: Probably the most surprising of the film.
• Shout Out: Her name may be a nod to Halloween 1978's Final Girl Laurie Strode.

Danielle

• Big Badass Wolf
• Cool Big Sis
• Ms. Fanservice: The entire girl gang are this.
• Our Werewolves Are Different
• The Reveal
• The Schlub Pub Seduction Deduction: The gang of girlfriends lure men into the forest and then eat them after stripping off their clothes and skin!

Maria

• Big Badass Wolf
• Ms. Fanservice: The entire girl gang are this.
• Our Werewolves Are Different
• The Reveal
• The Schlub Pub Seduction Deduction: The gang of girlfriends lure men into the forest and then eat them after stripping off their clothes and skin!

Janet

• Big Badass Wolf
• Ms. Fanservice: The entire girl gang are this.
• Our Werewolves Are Different
• The Reveal
• The Schlub Pub Seduction Deduction

Mr. Kreeg

Steven'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.

• Angry Guard Dog: He has a small dog named Spite.
• Badass
  • Badass Grandpa: He puts up a good fight against Sam, despite falling down a flight of stairs, and getting glass stuck in his hands.
• Chekhov's Gun: The chocolate bar Mr. Kreeg puts down before Sam arrives saves his life.
  • A more literal example is his early reference to owning a shotgun. Of course, the shot
• Dark and Troubled Past: The reason why he is a shut-in and hates Halloween.
• The Driver: Of the bus kids.
• Hikikomori
• Hopeless Boss Fight
• Jerkass
• Redemption Equals Death
• Shotguns Are Just Better: "I've got an NRA membership in my pocket, and a shotgun over the fireplace!"

Emma and Henry

A 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.

• Continuity Cameo: Emma and Henry appear throughout the film, often helping to establish continuity in the Anachronic Order.
• Cruel and Unusual Death: Since Emma is chronologically the last casualty in the film, Sam is so annoyed at this point with rulebreakers that he slashes her throat and then cuts her body up and hangs it on display about the garden.
• Dead Star Walking: Emma dies very early in the film.
• Lazy Husband: Apparently he sleeps for half the day, plays video games for the other, and likes watching sex tapes.
• Robot Girl: Invoked, but she's only wearing a costume.

Shadow Man

A 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.

• Fate Worse Than Death: Now that Sam's got his hands on him.