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11. Donnie Darko (2001)
Opening a month after September 11, 2001, and virtually ignored upon release, Richard Kelly's directorial debut now seems like both a snapshot of the seemingly safe but deeply ominous world we remember living in just before the planes hit, and a direct response to events that happened after it was made. — P.N.
12. Down By Law (1986)
Before the Sundance Film Festival essentially transformed it into mainstream Hollywood's minor league farm system, American indie film routinely produced weird hipster gems like Jim Jarmusch's deadpan debut Stranger Than Paradise. But his follow-up, the existential prison film Down By Law, was (arguably) even cooler and cultier, if only for the inclusion of surrealist beatnik idol Tom Waits. — A.O.
13. Easy Rider (1969)
While Hollywood was stubbornly ignoring the counterculture (or, worse, pandering to it with tone-deaf misfires), Peter Fonda and Dennis Hopper pushed all the right peyote buttons and hit the zeitgeist jackpot. Together with Jack Nicholson, the stoner auteurs shook up the film industry with this lived-in portrayal of sex, drugs, and rock n' roll, while inadvertently ruining "Born To Be Wild" for all future generations. — A.O.
14. Eraserhead (1977)
Any number of David Lynch's movies could be here, but his first feature remains a startling testament to the richness and variety of what one man can pull out of his own head, if he's determined to work as long as he has to to get it out. (Because Lynch kept running out of money, Eraserhead was in production off and on for five years.) The moral, as with the punk movement that exploded around the same time, is "do it yourself" — if the people you try to explain your dream to just look at you funny, get a camera and crew and just do it yourself. — P.N.
15. The Evil Dead (1983)
Sam Raimi's feverishly inventive, Karo-syrup-drenched, $400,000 horror movie is a Hollywood calling card that the director probably had to live down before he could persuade anyone to trust him with something like the Spider-Man franchise. But the legions of kids whose heads exploded as they watched this on video throughout the '80s will always be Raimi fans. (If you actually saw this in a theater at any point before 1984, you earn a lifetime coolness certificate.) — P.N.
16. Faster, Pussycat! Kill! Kill! (1965)
Russ Meyer's best-known (and least breast-obsessed) exploitation classic is the kind of fantasy that most people would only put on film if they already had plans to burn the negative before any respectable people could get a look at it. The first twenty minutes — featuring freelance dominatrix babes racing their sports cars in the desert and killing anyone who looks at them funny — are like a drive-in movie from Mars. What happens after that? I'm not sure. I usually just watch the first twenty minutes again. — P.N.
17. Fight Club (1999)
With the end of the millennium breathing down his neck, director David Fincher and his stars — Edward Norton, Brad Pitt, and Helena Bonham Carter — took a deep breath of their own and plunged into the deep end. Positioned to be the movie of a generation and a zeitgeist blockbuster, Fight Club proved too strange for most of the mass audience to take in on its initial release. But it refused to go away quietly and today lives on, a big bar of eye candy that talks like an unhinged and overcaffeinated street preacher. — P.N.
18. Freaks (1935)
Legendary horror director Tod Browning, a former man of the circus who had a real feel for the seedy carnival atmosphere, broke every rule of polite movie entertainment with this intense melodrama. (One woman claimed the film had caused her to have a miscarriage.) Many early Hollywood movies were rediscovered by audiences on the midnight movie circuit of the '70s; Freaks was one of the strongest and strangest. Its cult included the Ramones, who got an anthem out of the freak-show stars' chant of "Gabba gabba." — P.N.
19. Grey Gardens (1975)
Many listeners were surprised by Jacqueline Kennedy's blunt statements in recently released tapes from 1964. For me, however, the most shocking part of that interview was how closely the former First Lady's informal cadences mimicked those of her cousin "Little Edie" Beale, the eccentric and beloved star of this paean to impoverished gentry, defiant individuality, and the perils of utter denial. — A.O.
20. The Harder They Come (1972)
Like many films on the list, this offbeat, low-budget crime story failed during its initial run in theaters, then later gained an enthusiastic word-of-mouth following thanks to midnight screenings. But what truly makes the Jimmy Cliff vehicle a classic is its indelible soundtrack, which helped to introduce Jamaican reggae to the world. — A.O.