Brandon Plush
The Villain Protagonist of Headless Halloween, Brandon loves scaring people, especially those weaker than him like his little sister or his nerdy cousin. One year, Brandon decided to get revenge on his science teacher by playing a few mean Halloween pranks on him, but ends up getting chased off a ravine and dying. He then has to perform three good deeds in order to come back to life.
- Aesop Amnesia: His teacher and mother are frequently trying to show that his bullying behavior has consequences but he never listens. Not even dying is enough to set this kid straight.
- Alas, Poor Villain: Despite being an awful person, he's condemned to a lonely Fate Worse than Death, even after he went through hell to save his friends and admitted he missed his family.
- Asshole Victim: It's impossible to feel sorry for this kid after he receives his comeuppance.
- Big Brother Bully: He constantly torments his young sister, Morgan, and ditches her and her friends at a neighborhood at night the first chance he gets to spend Halloween with his friend.a
- The Bully: A rare example in that he's a bully who's also the protagonist.
- Cassandra Truth: He tries to tell Vinny that he can be strong and walk out of the haunted house they are in, but he doesn’t listen.
- Disney Villain Death: A surprisingly gruesome example. He outright runs off a cliff and falls onto jagged rocks at the bottom of a ravine. And we actually see his corpse later on when his ghost returns to the scene.
- Even Evil Has Loved Ones: As much of a callous jerk he is, Brandon does despair over how his family will react to his untimely demise and regrets that he can't spend his last moments with them. It's probably his only redeeming quality.
- Everyone Has Standards: He's a callous jerk, but when he briefly wonders if his actions got Cal killed, there's no mistaking the horror in his words.
- Hate Sink: He has absolutely no redeeming qualities and ends up killed.
- Heel–Face Door-Slam: By the end of the story, Brandon has risked his life several times to save the people he endangered in the first place and shows considerably more compassion for his friends and family than he ever did as a mortal. Unfortunately, Norband then reveals that he never had any intention of giving Brandon back his life and that he's trapped as a spirit forever. He then decides to go back to terrifying people with the other undead kids.
- Jerkass: Takes delight in tormenting and scaring others.
- Jerk with a Heart of Jerk: He doesn't actually care about helping other people, but he'll do it if it means he can come back to life.
- "Just Joking" Justification: He frequently says "Oops, just joking" when pulling pranks.
- Killed Off for Real: He actually dies halfway through the book, and is tricked into believing he could come back to life. It turns out that, no, he's dead for real.
- Lack of Empathy: He's incapable of feeling sorry for anyone unless he's forced to. It's telling how even his friend Cal, who's as much a bully as Brandon, and Brandon's wimpy cousin Vinnie have more integrity. Cal hesitates to abandon Brandon's sister and her friends on Halloween by pointing out they're only 7, isn't really comfortable leaving Vinnie in the haunted house, and doesn't want to leave Brandon at the mercy of Mr. Benson's dogs. Vinnie begs Brandon not to save him from the haunted house as he doesn't want Brandon to get captured too, even though Brandon was the reason he was trapped to begin with.
- Laser-Guided Karma: He falls to his death, is then tortured by Norband and the other dead children, forced to save three scared people thinking it will undo his death, and is then told this is a lie. At first, the ending seems to make him a Karma Houdini as he is more than happy to go back to scaring people, but he's still dead and there's no indicator he'll actually be allowed out of the Other Side.
- Mythology Gag: At the start of the book, he tells the kids he's babysitting of the tale of a boy spending the rest of his life looking for his head after getting it ripped off.
- Never Got to Say Goodbye: He's distraught over how he not only died from his own stupidity, but that he never got to tell his family how much he loves them and how he'll just be remembered as a nasty kid who tortured his peers.
- Nightmare Fetishist: He loves seeing people scream, cry, and vomit from fear. Of course, when he's on the other side of this naturally he's all talk and no game.
- Parting-Words Regret: Implied. He contemplates visiting his family before he's trapped in the other-side forever, obviously aware he was an absolute asshole to his sister and can never take that back.
- The Sociopath: Brandon has no redeeming qualities and gets off solely on tormenting those around him. What's more, while his mother is clearly disturbed by his destructive tendencies, his dad actually thinks it's funny and encourages him. That said, he isn't nearly as awful as Micah Brill or Tara Webster.
- Villain Protagonist: A clear example of a main character who deserves everything they suffer.
- With Friends Like These...: When Brandon and Cal are attacked by Mr. Benson's dogs, Brandon cowardly leaves Cal at their mercy as Cal begs for help.
Mr. Benson
Brandon's science teacher, a mountain of a man who has no patience for Brandon's cruelty and frequently tries to stop his victimizing the younger students.
- Adults Are Useless: Averted, with his one downfall being his inability to realize Brandon will never change. That said, he always steps in to punish Brandon for his cruel behavior.
- Cool Teacher: Kids like him because his science classes are always fun.
- The Golden Rule: He explains this to Brandon and tries to tell him that him pretending to spill acid on Vinny is a violation of this rule.
- Hero Antagonist: He antagonizes Brandon by lecturing him and making him do extra work as punishment for tormenting others, and since Brandon's a Villain Protagonist it puts Benson in this role.
- Hunk: Brandon's narration describes him as a well-muscled hulk of a man fond of flannel shirts and jeans, giving an image of a rugged mountain man.
- Papa Wolf: Do not try to play mean jokes on his students as he will definitely punish you for it.
- Reasonable Authority Figure: Brandon's the only kid who hates Benson because he's this trope, since Benson shows no tolerance for bullying or cruelty.
- Small Role, Big Impact: He only appears at the beginning to tell off Brandon for his behavior. Plush's subsequent vandalism of his house on Halloween is what sets off his terrifying journey to the afterlife and failed attempt at redemption.
- Stern Teacher: To Brandon, whose punishments are no more than he deserves.
Norband
A mysterious boy who just happens to have the same unique monster mask Brandon Plush owns. Brandon encounters him in Headless Halloween after getting on the other side of Raven's Ravine. Norband leads Brandon to a Halloween party in a creepy neighborhood, and then shows him what it's really like to be scared.
- Cool Mask: He wears the exact same of horrible monster mask Brandon has.
- Enemy Without: He's some kind of weird doppelganger of Brandon, but claims he "dressed up" as Brandon for this year.
- Good is Not Nice: He only comes across as villainous in that he's giving Brandon a taste of his own medicine. It reads as Norband trying to get Brandon to understand how he makes his victims feel.
- Losing Your Head: When he takes off his mask he reveals he has Brandon's face. But then he takes that off as well and reveals he has nothing above his neck.
- Our Angels Are Different: He's implied to be some kind of angel or spirit. He doesn't have an actual name or face and his entire role was to show Brandon what it's like to be on the Other Side, as in the other side of being scared.
- Significant Anagram: Norband is another way to spell Brandon.
- Yank the Dog's Chain: He tells Brandon he can come back to life if he can save three scared people. When Brandon manages to do just that, Norband tells him "Oops, just joking!" However, when Brandon shows he's learned absolutely nothing from this whole experience, it comes into question if he would've really deserved to come back anyway.
Cal, Vinnie, and Maya
Brandon's best friend, cousin, and sister respectively, who accompany him on Halloween and are thrown into danger by his malicious antics. Brandon now has an hour to right his wrong and save them all before he loses his life for good.
- Asshole Victim: Subverted. While Cal was a huge jerk and bully like Brandon, he's still more empathetic as he didn't want to abandon little Maya and her friends on a dark, dangerous night. Plus Brandon has to save him as his first act of redemption.
- Break the Cutie: Not only are Maya and Vinnie frequently victim to Brandon's scummy bullshit, but they get lost on Halloween and fall into danger. Then Brandon saves them, only to "die" mere minutes later, with Maya herself witnessing her brother drop dead and become a ghost. The poor kids are gonna be reeling from this for a while.
- Cowardly Lion: Vinnie is supposed to be a cowering, easily frightened little boy. Nonetheless when he's trapped in a haunted house of certain doom, he yells for Brandon to save himself rather than risk his own life to save him.
- Even Evil Has Standards: Cal may be a hooligan and bully as well, but he's very uncomfortable with how Brandon treats Maya and Vinnie and is genuinely worried for the kids' safety.
- I Will Only Slow You Down: Vinnie initially yells for Brandon to save himself when the latter comes to save him, showing he may not be as big a coward as Brandon thought.
- Morality Pet: Downplayed. While it's Brandon's fault they're in danger to begin with and he doesn't have a choice but to rescue them, it's implied Plush harbors guilt that they could die because of him, and he shows genuine concern for their safety.
- Mundanger: Compared to Cal and Vinnie, Maya's peril isn't obviously life-threatening or supernatural and merely has her and her friends lost in a dark, dangerous part of town being menaced by vicious strangers. The situation is terrifying regardless.
- Sapient House: Vinnie finds himself trapped in a mysterious old house that's apparently sentient and keeps ghosts as pets, which might have consumed him and taken his spirit as well.
