Legends of Halloween is a 2017 Anthology Comedy Horror film with six segments. It is starring Jennifer Stone, Chloe Grace Moretz, Tyler Posey, Ansel Elgort, Jennifer Lawrence, Bailee Madison, Mila Kunis, Jake, T. Austin, Cameron Boyce, Dove Cameron, Miranda Cosgrove, Kirsten Dunst, Jennifer Love Hewitt, Skai Jackson, Billie Lourd, Lea Michele, Anna Paquin, Evan Peters, Norman Reedus, Chandler Riggs, Emma Roberts, Josie Totah, Rutina Wesley, Tyler James Williams, Scott Wilson, Kevin Zegers, Eliza Dushku and Jamie Lee Curtis.
The film starts with the front door of a house opening, a POV shot going down a hallway and turning to the living room, where Adam (Josie Totah) sits. The camera approaches and it cuts to Jess (Jennifer Stone) scaring him. He asks if she has any stories and she smiles, saying "I have a hell of a story for you."
The segment begins with Mandy (Chloe Grace Moretz) watching tv when her phone rings. She answers, revealing it to be her friend, Claire. (Billie Lourd) As they talk, Mandy hears shuffling upstairs and checks the kids. She walks back downstairs and opens the door to reveal trick or treaters. As she hands them candy, she sees a woman in black standing on the lawn. When the kids leave, she threatens her and closes the door. She talks to Claire more when Claire cusses and screams, the call dropping. Mandy sees a shadow in the kitchen and looks outside to see the woman in black walking across the grass. Mandy locks the door and notices the woman had disappeared. She hears a crash and screaming upstairs and runs as fast as she could when she enters, letting out a scream as the woman is eating the children. The woman looks up at her and jumps to her as she screams.
Jokes on You
Brady (Tyler Posey) is walking down the street while kids run past him. He turns around to see a man in a skull mask following him everywhere he goes. He notices he's alone on one street when the man chases him and tackles him down. He cries for help to no avail as the man covers his mouth and nose with a rag. Soon, he awakens and sees he's tied up. The skull mask is lifted off to reveal Mike, (Tyler James Williams) a former friend of his. Mike tells of the prank Brady played on him that ruined his reputation and forced him to change schools. Mike pulls Brady's head back and uses pliars to remove a tooth, making him scream. He tortures him in many ways, stabbing needles into his arms, removing some of his teeth and even chopping a finger off. Mike ends up putting tape over his mouth, then shoving a plastic bag over his head, laughing as Brady resists and eventually suffocates. Mike leaves the shed and sees the woman in Black, telling her the body's all his and thanks her before leaving.
A troubled teen, Randy, (Ansel Elgort) is sitting in his room when Mike texts him a picture of the dead Brady. Randy texts back, saying he didn't think he'd do it when his mother (Kirsten Dunst) calls him for dinner with another family. He sits down with his mother, father, (Norman Reedus) His brother, Austin, (Jake T. Austin) and the other family. (Jennifer Love Hewitt, Kevin Zegers, Miranda Cosgrove) While they eat, Marie, (Hewitt) asks what the meat is, which Randy's dad replies with, "Human." The family gasps when Randy's family reveal themselves as vampires and massacre the entire family. Randy drags one body to his grandpa (Scott Wilson) who stands for the first time in a year. They then go back to the feast when Austin reveals he has to go out with some friends.
Sarah (Jennifer Lawrence) is arguing with her fiance over the phone when she almost hits a teenage girl. (Emma Roberts) Sarah follows her to ask what's happening to her and she reveals she is being chased by a clown. She leads Willa to the car but as soon as they begin to drive, Willa screams. They pull up to a gas station and they get out, Willa opening the door in back. She claims he was back there. Sarah goes to the gas station for help while Willa stays outside. Sarah is talking to the manager, Deb, (Anna Paquin) when a clown enters the building with Willa. Willa runs to Sarah when the clown attacks everyone, saving Sarah for last. He then sets the place on fire before walking to the woman in black and telling her it looks like an accident.
This sequence taking place before all the others, Sophia, (Bailee Madison) Kyla, (Skai Jackson) and Cam (Cameron Boyce) take out a Ouija Board and ask to talk to a spirit. As they ask it questions, they forget to say goodbye at the end and unknowingly allow it out as they go upstairs, a hand flies out of the board. Cam returns downstairs for a drink and realizes something happened with the board. He picks up a piece and looks through it, seeing the woman in black when she slashes her hand, cutting his throat. Kyla decides to look for him and opens the door, the woman standing infront of her. She punches her hand through her chest, ripping her heart out and eating it. Sophia fights the woman and ends up knocking her out the window. She looks out but can't find the body when a hand grabs her from above and lifts her into the sky, then dropping her infront of the house. Austin sees this and looks up when the woman flies to him and stabs his heart, making him turn to dust.
Woman in Black
Tera (Mila Kunis), a demon, is watching over the houses, Hearing Randy eating the family, seeing Austin getting dusted, Brady getting kidnapped and comes across the house Mandy is babysitting for. She hears Mandy scream and enters the house to see Mandy being gutted by the woman in black. Tera rips the hood off to reveal Jess. Jess screams and attacks Tera.
Adam is disatisfied with the stories, as it could never happen. Jess smiles as she points to the tv station, the news. The reporter mentions the murders and missing bodies and burning of the gas station. Adam looks at her as her eyes glow red. He screams as she twists his head around and tosses his body. She says, "Happy fuckin' Halloween," then sitting on the couch, eats his candy.
- Jennifer Stone as Jess, A babysitter who is revealed to be the woman in the black cloak.
- Josie Totah as Adam, Jess' final victim of the night.
- Chloe Grace Moretz as Mandy, A babysitter who is stalked by the Woman.
Jokes on You
- Tyler Posey as Brady, a high school jock and bully.
- Tyler James Williams as Mike, a boy looking for revenge.
- Ansel Elgort as Randy, a troubled teen who is secretly a vampire.
- Kirsten Dunst as Wendy, Randy's mother.
- Norman Reedus as Walter, Randy's father.
- Jake T. Austin as Austin, Randy's brother.
- Jennifer Love Hewitt as Maria, a victim of the family.
- Miranda Cosgrove as Maria's daughter.
- Kevin Zegers as Maria's husband.
- Scott Wilson as Grandpa, an elder vampire.
- Jennifer Lawrence as Sarah, a woman going through a divorce.
- Emma Roberts as Willa, a teen being attacked.
- Anna Paquin as Deb, the gas station manager.
- Billie Lourd as Claire, Mandy's friend who is attacked.
- Lea Michele as Melissa, a teenager.
- Bailee Madison as Sophia, a gothic teen.
- Skai Jackson as Kyla, Sophia's best friend.
- Cameron Boyce as Cam, Sophia's friend.
- Jamie Lee Curtis as Mrs. Esmeralda, a fortune teller who warns the three.
Woman in Black
- Mila Kunis as Tera, a demon.
- Rutina Wesley as Mike's Mother.
- Dove Cameron as Customer.
- Evan Peters as Clown.
- Chandler Riggs as Stoner.
- Eliza Dushku as angry driver.
- Brady - Arms stabbed with needles, teeth pulled out, finger chopped off and suffocated by Mike.
- Maria's family - Eaten by Vampire family.
- Cam - Throat slit by the Woman in Black.
- Tera - Heart ripped out by The Woman In Black.
- Sophia - Lifted into the sky and dropped onto Pavement.
- Austin - Stabbed in the heart and dusted by the Woman In Black.
- Customer - Head smashed by clown's hammer.
- Deb - Shotgun taken, smashed against face and shot in stomach.
- Willa - Throat slit.
- Claire - Stabbed multiple times in the back.
- Melissa - Head smashed against the counter.
- Sarah - Stabbed in the chest, gasoline poured on her and lit on fire.
- Stoner - Gasoline poured down throat, weed lit in mouth and set on fire.
- Angry Driver - Pulled out of car by clown and run over by car.
- Two Children - Eaten by the woman in Black.
- Mandy - Gutted and Eaten by The Woman In Black.
- Tera - Attacked by Jess/Woman in Black.
- Adam - Head twisted around by Jess.