Sleepy Hollow (1999)

Tim Burton's morbid, fog-filled Sleepy Hollow is cloaked in mystery and intrigue, but it also captures the (spooky) spirit of fall flawlessly. The Oscar-winning film, starring Johnny Depp as the quirky Ichabod Crane and Christina Ricci as his curious love interest, pulls back the veil on the legend of the Headless Horseman. But more than that, it satisfies all our desires for a dark, brooding autumn picture.