The Hollow tells the story of Ian Cranston, a high school teen who has just found out he is the descendant of Ichabod Crane. With the help of his girlfriend Karen, a local bully named Brody, and the old cemetery caretaker Claus Van Ripper, Ian now must stop the newly resurrected Headless Horseman.
Tropes used in The Hollow include:
- All Part of the Show: The participants in the Ghostly Hayride initially assume that Erica's panicked appearance, and subsequent decapitation by the Headless Horseman are all part of the ghost tour.
- An Axe to Grind: Klaus' preferred weapon is an axe. On being rescued from the police cruiser, his first act is to return to the graveyard to retrieve his axe.
- Chekhov's Skill: During fencing practice, Ian demonstrates an unconventional (and illegal) move. He later uses this same move in his final battle against the Horseman.
- Crusty Caretaker: Claus is the caretaker of the cemetery, who staggers through the film uttering dire warnings and generally being taken for a crank and a drunk. He also serves as a Haunted House Historian for all matters related to the Headless Horseman.
- Death by Sex: Erica and Rob decide to have sex in the old shed in the graveyard. Rob is performing cunnilingus on Erica when he is decapitated by the Horseman.
- Definite Article Title
- Glory Days: Ian's father Carl is the high school football coach who is determined that Ian will have exactly the same high school experience as him, including being a football hero. He ignores the fact that Ian is more interested in drama than athletics.
- Haunted House Historian: Crusty Caretaker Claus knows everything there is to know about the legend of the Headless Horseman, and the lineage of Ichabod Crane; including how to destroy the Horseman permanently.
- Headless Horseman: The villain of the movie is the Headless Horseman returned to kill the last of Ichabod Crane's line.
- I Shall Taunt You: At one point, the Headless Horseman attacks Carl and is about to kill him when Ian shows up and calls him a coward. Enraged, the Horseman lets go of Carl and chases Ian instead, which Ian was counting on.
- Jerk Jock: Brody is the quarterback and captain of the football team. He spends his time playing cruel practical jokes, forces others to do his homework, and regards Karen as his personal property.
- Off with His Head!: The Headless Horseman dispatches his victims by decapitating them with a cavalry sabre.
- The Place
- Stingy Jack: The Headless Horseman has a massive jack-o'-lantern in place of his head. He can remove it and carry it under his arm.
- Supernatural Repellent: The Headless Horseman cannot cross the old covered bridge, so victims can escape him by running across it. Later it is discovered that the Horseman bursts into flame if he is forced on to the bridge.