Movies Like The Legend of Sleepy Hollow

If you liked The Legend of Sleepy Hollow (1985), a horror and comedy movie directed by Edd Griles, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
The Legend of Sleepy Hollow (1949)
★ 7.4/10Also family and horror
Washington Irving's tale of Ichabod Crane and the headless horseman is brought to life, narrated by Bing Crosby.
2
The Adventures of Ichabod and Mr. Toad (1949)
★ 6.5/10Also horror and family
A concise adaptation of Kenneth Grahame's "The Wind in the Willows" about Mr. Toad's motor mania, followed by a short retelling of Washington Irving's "The Legend of Sleepy Hollow" concerning schoolmaster Ichabod Crane.
3
Mostly Ghostly (2008)
★ 6.1/10Also family and horror
Based on the successful book series by R.L. Stine, this spooky tale finds 11-year-old Max making a deal with the ghosts who haunt his home. If Max helps them find what was responsible for their parents' disappearance…
4
Night of the Demons 2 (1994)
★ 6.2/10Also horror and comedy
Angela, the hostess from hell, summons her army of teen demons when teenagers from St. Rita's High School decide to party at the haunted Hull House on Halloween.
5
The Curse of Bridge Hollow (2022)
★ 6.6/10Also comedy and horror
A Halloween-hating dad reluctantly teams up with his teenage daughter when an evil spirit wreaks havoc by making their town's decorations come to life.
6
High Spirits (1988)
★ 5.8/10Also comedy and horror
When a hotelier attempts to fill the chronic vacancies at his castle by launching an advertising campaign that falsely portrays the property as haunted, two actual ghosts show up and end up falling for two guests.
7
Night of the Demons (1988)
★ 6.2/10Also horror and comedy
When partygoers at a deserted funeral home decide to have a séance on Halloween night, they awaken something evil with a thirst for blood.
8
Casper (1995)
★ 6.4/10Also comedy and family
Casper is a kind young ghost who peacefully haunts a mansion in Maine. When specialist James Harvey arrives to communicate with Casper and his fellow spirits, he brings along his teenage daughter, Kat. Casper quickly…
9
Boo! A Madea Halloween (2016)
★ 5.8/10Also comedy and horror
Madea winds up in the middle of mayhem when she spends a hilarious, haunted Halloween fending off killers, paranormal poltergeists, ghosts, ghouls, and zombies while keeping a watchful eye on a group of misbehaving…
10
Mostly Ghostly 3: One Night in Doom House (2016)
★ 6.2/10Also family and horror
Just one enchanted jewel stands between earth and an army of evil spirits led by the devious ghoul, Phears. With the help of his new girlfriend and ghost pals, Max Doyle races to find the crystal and save the world.
11
The Fearless Vampire Killers (1967)
★ 6.9/10Also comedy and horror
A noted professor and his dim-witted apprentice fall prey to their inquiring vampires, while on the trail of the ominous damsel in distress.
12
Once Bitten (1985)
★ 5.8/10Also comedy and horror
Mark wants to lose his virginity, but his girlfriend wants to wait. Unfortunately for both of them, a 400-year-old vampire Countess needs to turn a virgin into a vampire before Halloween in order to preserve her own…
13
Goosebumps 2: Haunted Halloween (2018)
★ 6.1/10Also comedy and horror
Be careful what you wish for. With their after school junk business, best friends Sonny and Sam hope to find treasure in other people’s trash. But when cleaning out the old Stine house, they open a locked book that…
14
My Best Friend Is a Vampire (1987)
★ 6/10Also horror and comedy
Shortly after high school student Jeremy Capello goes on a hot date, he finds he can't stand garlic or see his reflection in mirrors.
15
Scooby-Doo! and the Curse of the 13th Ghost (2019)
★ 7.8/10Also comedy and family
Mystery Inc. withdraws from solving crimes after botching a case. When Vincent Van Ghoul contacts the gang about an unfinished investigation from Daphne, Shaggy and Scooby's past, the gang springs into action to finish…
16
Trick 'r Treat (2007)
★ 7/10Also horror and comedy
Four interwoven stories that occur on Halloween: an everyday high school principal has a secret life as a serial killer; a college virgin might have just met the one guy for her; a group of teenagers pull a mean prank…
17
Fright Night (1985)
★ 7.1/10Also comedy and horror
Charley Brewster, a high school student, accidentally discovers the true and creepy nature of Jerry Dandrige, his dashing and enigmatic new neighbor; but no one seems willing to believe him.
18
A Babysitter's Guide to Monster Hunting (2020)
★ 6.2/10Also family and comedy
Recruited by a secret society of babysitters, a high schooler battles the Boogeyman and his monsters when they nab the boy she's watching on Halloween.
19
Scared Shrekless (2010)
★ 6.8/10Also comedy and family
Shrek challenges Donkey, Puss in Boots and his other fairy tale character friends to spend the night in Lord Farquaad's haunted castle, telling scary stories to see who can resist becoming scared and stay the longest.
20
Little Monsters (1989)
★ 5.8/10Also comedy and family
A young boy is scared of the monster under his bed. He asks his 6th grade brother to swap rooms for the night as a bet that the monster really exists. Soon the brother becomes friends with the monster and discovers a…