4. Fight Club
Do you know someone who owns this film? Sure you do. Better question: do you know someone who quotes this film constantly and thinks it's the best thing ever in the world ever???? Yep, this one falls square in the "loyal following of fans" category of cult classic. Sure, it's got Brad Pitt being so manly that people get into underground fistfights just cause he says so, but it's not perfect. That being said, the film is tough as nails and very entertaining, and was practically built from the ground up to have a cult following. It's about a cult!!
Edward Norton's character at one point realizes that he's created a monster that he can't stop. He begs his followers to not do what they want to do, but he's trained them to ignore him. It's like he built an escape-proof death room and then accidently locked himself in. The panic in his eyes as he realizes the full extent of his powerlessness is soul-crushing.
5. Evil Dead 2
You really think I'm going to have a list of cult classics without paying tribute to the King? Hail to the King, baby! Bruce "Groovy" Campbell accidentally lets loose a force of evil while staying in a cabin in the woods and has to fight them. In the process EVERYONE other than Bruce dies and Bruce loses a hand. Don't worry, he attaches a chainsaw to the stump (I know, right?!) It's fun, scary, funny, gory, and directed by Sam "Best Spider-Man director to date" Raimi. But it's also sad.
Remember the part where we said Bruce was the only survivor? Well one of the corpses was his girlfriend, the reason he wanted to go to the cabin in the first place. He has a few tender moments with her, gives her a present that's clearly sentimental to him, and then she gets possessed. Not only is Bruce forced to dispatch her, but then her corpse mocks him until he dispatches her again. That's cold, that's evil... dead? (Dr. Evil pinky grin.)