15 Best Dark Fantasy Movies Of All Time

15. Sleepy Hollow (1999)

Spoiler alert: Tim Burton features multiple times on this list. Why wouldn't he? The famous director could have his own individual list full of weird and wonderful fantasy films. Not to mention frequent collaborator, Johnny Depp, who stars in many of Burton's films.

Sleepy Hollow from 1999 is the duo's third collaboration and arguably their creepiest production. Based on the famous 1820 short story by Washington Irving, Depp plays police detective Ichabod Crane who is sent to the eerie titular village to investigate a string of decapitations by an apparition known as The Headless Horseman.

The film is everything a dark fantasy should be. The Gothic setting is full of creepy, haunted imagery and iconic set design from The Tree of the Dead to The Haunted Pumpkin. The supernatural horror elements are heightened by the intimidating presence of The Headless Horseman, and the dark humour contributes to the unnerving atmosphere.

Sleepy Hollow may have become forgotten over time, especially in the rank of Johnny Depp's success, but the film still holds up today. It currently sits at a respectable 69% critic score on Rotten Tomatoes, and it grossed a reasonable $200 million at the worldwide box office.

Sleepy Hollow also won the Academy Award for best art direction at the 2000 Oscars which serves as a testament to the film's dark fantasy realism.