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21. Harold and Maude (1971)
A deeply romantic, life-affirming movie dressed up as an outrage of a black comedy, Harold and Maude was the perfect movie for its shell-shocked era. You could say that only in 1971 could Bud Cort and Ruth Gordon pass for movie stars, let alone as a movie-star couple. But then, a lot of people who love this movie weren't even born in 1971. — P.N.
22. Heathers (1989)
Though far from the first movie to rip the lid off high-school life, Heathers' formula for black comedy — murderous slapstick and invented, baroque teen slang — made it one of the most influential cult hits of the late '80s. It set off a wave that Joss Whedon caught and rode like Moondoggie. And did I mention that I love my dead gay son? — P.N.
23. Kiss Me Deadly (1955)
Mickey Spillane's novels about the detective Mike Hammer pushed the hard-boiled genre about as far as it could go, and director Robert Aldrich's movie version pushes it over a cliff. Kiss Me Deadly's take on the ruthlessness of film noir is so extreme that it crosses into parody, and keeps going until it becomes something close to hard-boiled science fiction. Quentin Tarantino famously tipped his hat to it with Pulp Fiction's glowing suitcase. — P.N.
24. The Man Who Fell To Earth (1976)
Nicolas Roeg's poison-pen letter to America stars David Bowie as a reclusive genius-businessman, who's actually an alien visitor who just wants to make his fortune and get the hell back to his home planet. No other movie has managed to make our planet look so ravishingly, frighteningly beautiful while basically making a case for why we ought to just blow the place up and start over. — P.N.
25. Mommie Dearest (1981)
Movies that knowingly court ironic cult status rarely work. Instead, the classics tend to be the ones that fully commit to their own weirdness, like this over-the-top adaptation of the bitter, score-settling memoir by Joan Crawford's daughter, Christina, featuring a sincerely unhinged performance by Faye Dunaway as the (allegedly) monstrous screen diva. Say it with me, drag queens: "No... wire... hangers!" — A.O.
26. Monty Python and the Holy Grail (1974)
Holy Grail is the kind of historical burlesque you could only get from people who are serious enough students of history to know how ludicrous most of it is. It's also one of the most compulsively quotable primary artifacts of the geek universe. (It's sobering to think that, without this movie, someone could say he has three questions without reducing half the people within earshot to hysterics.) — P.N.
27. Mothra (1961)
Japanese monster movies are a whole denomination of cult films unto themselves, and we'll probably get some grief in the comments section for not representing the subgenre here with its biggest star, Godzilla. But our Saturday afternoon hearts will always belong to Toho Studios' giant psychic moth. Not only is she a kick-ass chick, but she travels around with a pair of tiny priestesses who sound like The B-52s! — A.O.
28. Night of the Living Dead (1968)
George Romero's $114,000 independent production came out of Pittsburgh to spread across the planet, powered solely by stunned word of mouth. At first, the closest thing it earned to reviews was a string of angry editorials (including one by the young Roger Ebert) wondering how anything so nasty could be exhibited in theaters. One measure of how influential it's been is that zombies are now the biggest players in horror, with the possible exception of lovesick vampires. They'd always been the also-rans of the monster derby, until Romero gave audiences a good look at what they're like when it's feeding time. — P.N.
29. Office Space (1999)
Mike Judge's first foray into live action was quietly released and received mostly tame reviews, but was picked up on video and spread like wildfire among viewers for whom its juicy satire of cubicle drudgery struck a nerve. Eager to learn from its mistakes, the studio that produced Judge's next feature, Idiocracy, did its best to not release it at all. — P.N.
30. Pee-Wee's Big Adventure (1985)
A dual triumph for its deep-in-character star, Paul Reubens, and its first-time director, Tim Burton, Adventure captures a certain kind of mid-'80s sensibility. It's a live-action-cartoon tribute to kitsch, with one crowd-pleasing foot in the multiplex and one in the art scene. — P.N.