I used to be way more into film. Who would have guessed that it would be surpassed by TV? I agree with whoever pointed out that TV is better for storytelling, and film is better for blowing your mind. Anyway, this list is slanted toward old stuff, and there must be some new stuff that I haven't seen yet. I left them unnumbered, but they are loosely arranged with the ones I like better closer to the top.
Brazil
(1985) Terry Gilliam is a creative genius but he needs some reining in. In Brazil this was done by the low budget, by Tom Stoppard writing several drafts of the script, and finally by the studio, which pressured Gilliam to cut the American theatrical version down to 131 minutes. This should not be confused with the dreadful 94 minute "love conquers all" version, which was shown only on American television. The Criterion "director's cut" is pretty much the same as the 142 minute European theatrical version, and I think the extra 11 minutes bog the film down and add nothing. Unfortunately, the 131 minute version has never been released on DVD, only on VHS and videodisc. (It might say 131 when you order it, but the actual DVD will be 142.)
Anyway, even the bloated version is one of the best films of all time. As Danny Peary wrote, "Every shot is bizarre and fascinating." Although it's usually not considered steampunk, I would call it the most important example, because it's the most popular and acclaimed vision of an alternate technological world, mixing devices and styles that we find new, old, and unfamiliar. Of course, like Kafka, Gilliam is really showing us our own world. In one of the most important shots, the camera backs and rises from a vehicle on a highway to show it walled in on both sides by endless billboards with scenes of beauty and happiness, while on the other side is industrial wasteland all the way to the horizon. In another key shot, a secretary cheerfully types a transcript of a screaming tortured prisoner in the next room.
Brazil is a pessimistic film about revolution. It creates a nightmarish order that we want to destroy, and then begins to destroy it. Characters and locations -- the plastic surgery victim, Sam's apartment -- are more disordered each time we see them. As Sam tries to fight the system, his own life unravels. When he kills the dream monster and removes its mask, he sees his own face. Sam is bound to the structures he wants to destroy, and in the end he can only escape by destroying his own sanity.
The Good, The Bad, and The Ugly
(1966) Sergio Leone, an Italian, was obsessed with the American west, and made westerns that were far more authentic than anything coming out of Hollywood. Tarantino called this the best directed film of all time, and I agree. In his instincts for where to point the camera, Leone is a master storyteller. Several things combine to elevate this far above his other films: the overall grittiness and chaos, the scene where the prisoners play music to cover up the sound of torture, Eli Wallach's performance as Tuco, and the soundtrack, which is Ennio Morricone's best work. Some scenes are technically music videos, because Leone had Morricone record the music first, and then shot and edited the film to fit it.
Leone is seldom credited for his political message: in a capitalist society, every time money changes hands, someone dies. The characters are introduced according to this rule. Angel Eyes, the Bad, is offered money to spare a man's life, and instead kills him and takes it as payment to also kill the man who bought the first killing; so he follows the rule even against the wishes of the payer. Blondie, the Good, subverts the rule by turning in fugitives for bounty and then freeing them.
Point Break
(1991) Roger Ebert, reflecting on The Good The Bad and The Ugly, said that he rated it four stars because of its apparent trashiness, but wrote a five star review, and only with time did he overcome cultural bias to see it as objectively great. That's how I feel about Point Break. No film has ever made me feel more alive than this dumb FBI surfer bank robber movie.
Keanu Reeves would later become a huge star with The Matrix, but this, his first action role, is the same story as the Matrix but in our own world, with full darkness. "Morpheus" is morally ambiguous; the liberation he offers is temporary and fleeting; aliveness in this world is crushed down, and can only survive on the other side of some uncanny veil. It's actually a lot like Wuthering Heights.
The Third Man
(1949) A perfect conjunction of a great script and cast, skilled and innovative direction, and a radical and beautiful zither score by Anton Karas. The first time I saw it, it was an old print that had faded on the outside, so in the final shot, which is already one of the best shots in film, there was an accidental effect that made it even better: everything just got brighter and brighter and turned to white.
Eternal Sunshine of the Spotless Mind
(2004) This is a science fiction film: it introduces a miraculous technology -- in this case, one that removes memories -- and explores its unintended consequences. At the same time, it has more depth than most films in the literary genre. This is something that has been tried many times and rarely achieved: a love story with a fantasy/sci-fi element that carries it to greater emotional power than you could ever get with strict realism. Also, this may be the only film whose title is in iambic pentameter.
Bring Me The Head of Alfredo Garcia
(1974) The only film Sam Peckinpah had total control over, and one of the most politically radical films ever made. At the beginning we think we're in the old west, as a Mexican warlord beats his daughter to find out who got her pregnant, and then declares the title line, offering a million dollars. In the next shot, a jet airplane lands! We discover that this world run by violent gangs and hired killers is our own world.
The protagonist, Warren Oates in his greatest role, is a lazy bar owner who hears about the bounty from two thugs and decides to track down Garcia. SPOILER: Eventually he finds him already dead, and spends most of the rest of the film carrying the head around as it decays. He begins talking to it, comes to sympathize with Garcia and against the bounty hunters, and ends up carrying the head up the murder-for-money hierarchy, killing everyone!
Galaxy Quest
(1999) This is why I disparage "the literary genre", a mere flavor of fiction that holds itself up as the sole gateway to high quality. This perfect film channels the luminous Divine and will never be taken seriously because it's also silly and fun.
The President's Analyst
(1967) Amazing sixties comedy with James Coburn as a psychologist hired to work with the president. Under stress and increasingly paranoid, he goes on the run, and is chased by spies from every nation. Then he teams up with a Russian agent to fight the real enemy, which you will never guess. In the best scene, where a bunch of agents kill each other in a grassy field, the DVD version uses a Barry McGuire song, but I love the uncredited song in the VHS version.
Repo Man
(1984) Another brillant silly film, and it has only improved with time.
Tideland
(2005) Michael Palin said this was either Terry Gillam's worst film, or his best. I think it's his second best, not as epic or concentrated or mind-blowing as Brazil, but more mature, more alive, and much more raw. A little girl wanders into a world between her own daydreams and a family of rural oddballs, and the whole vibe is so wonderful that if it were a little less dark, it would be utopian.
The Wages of Fear
(1953) Like Leone's westerns, this is an action film with a political subtext made by an art film director. A bunch of European expatriates are stuck in a crappy town in South America, without the money to leave. Then an oil well fire gives four of them the chance to make a bunch of money by driving two trucks full of nitroglycerine over a series of obstacles.
The Conversation
(1974) Between The Godfather and Apocalypse Now, Francis Ford Coppola made his most perfect film. Gene Hackman plays a surveillance expert who records a conversation and gets caught in a murder plot.
Metropolitan
(1990) I loved this when it came out. Even on the first viewing it seemed drenched in nostalgia, as if I was one of the characters grown old and looking back on the best days of my life. It's about a group of prep school kids who are like the last members of a dying race. Raised in a world of formality and intellect, they learn that they are powerless in the vulgar, hedonistic outside world. This is a coming of age film in which coming of age is a metaphor for the decline of civilization! The characters are introduced in formal dress at an elite party, and end the film hitchhiking.
Stroszek
(1977) Werner Herzog once said, "America is the most exotic country in the world." You can see some of what he meant in this depressing film about three Germans who move to rural America. The final shot, with the chickens, is so troubling that Herzog's crew refused to film it and he had to do it himself.
Two Lane Blacktop
(1971) Like Stroszek, this is a story of the emotional bleakness of the wide open spaces of America. Rock stars James Taylor and Dennis Wilson play a driver and mechanic team who do amateur racing. The driver never speaks while driving and the mechanic never speaks while working on the car. None of the characters have names. They pick up a girl, and then meet Warren Oates in a yellow GTO and agree to race him across the country. Then, in a move that would be unthinkable ten years later, the characters and filmmakers all seem to forget about the race, and focus instead on the relationships.
Cutter's Way
(1981) The young Jeff Bridges is already playing his favorite role, a slacker who gets drawn into being a hero. In this case, he helps a friend seek justice against a wealthy killer. Atmospheric and vastly underrated.
Fight Club / The Matrix
(1999) In the most important film of 1999, a depressed corporate drone breaks free into a world that is more dirty and real. There he leads a gang of violent revolutionaries, bombs an office building, and at the end, dies and comes back to life.
Safe
(1995) Challenging film about a woman who develops multiple chemical sensitivity, apparently from the emptiness and disconnection of modern life.
Ms.45
(1981) Abel Ferrara's greatest film. A mute woman gets raped twice in one day, flips out, kills the second rapist, and takes his gun, a huge .45 revolver. Then she dresses up and goes out killing sleazy men with less and less of a good reason.
Bad Lieutenant
(1992) Abel Ferrara's other greatest film.
Chinatown
(1974) Since the invention of test screenings, it is no longer possible for Hollywood to make a film with such a challenging ending.
Taxi Driver
(1976) The weird happy ending only makes sense if Travis Bickle is dreaming it as he dies.
Groundhog Day
(1993) The film that has made me feel most alive after Point Break. The ending is bland and I don't like Andie McDowell, but I wish there were a thousand films where someone is stuck in a time loop, and only one where a cop battles terrorists. Because really there's only one thing you can do with that, and there are all kinds of things that can be done with a time loop, and haven't.
Time Bandits
(1981) The middle of the film is lame. But the beginning is clever and promising -- my favorite bit is the TV game show "Your Money or Your Life". And the last 40 minutes, from the appearance of the Fortress of Ultimate Darkness to the end, is as good as anything ever put on the screen: exciting, beautiful, and totally bizarre, with a dark, trippy, unsettling ending that would be radical in any film, and is shocking in a film for kids.
Desperate Living
(1977) The purest and most epic realization of John Waters' artistic vision, and the trashiest. Mink Stole gives my favorite performance that is technically bad acting.
Man Bites Dog
(1992) Black comedy about a crew of documentary filmmakers who follow a serial killer. This was the inspiration for the Tarantino script that Oliver Stone dumbed down into Natural Born Killers.
Dr. Strangelove
(1964) Stanley Kubrick was a nerd in the best and worst sense: brainy, meticulous, but with a shallow understanding of human emotion that makes his serious films empty and sterile. The deepest character in his whole career is HAL, the computer in 2001; and this, his greatest film, is a comedy. Its view of the elite as blundering children is more interesting than the omnipotent menacing portrait in Eyes Wide Shut.
Mulholland Drive
(2001) David Lynch's one great film, maybe because he had to condense it down from a canceled TV series so it's packed with his best ideas. Interpretive SPOILER: the party is real and almost everything else is imaginary.
Stranger Than Paradise
(1984) My generation's Citizen Kane. Everything radical about it has been imitated to the point that it seems normal, but when I first saw it in the 80's, I couldn't stop thinking about it for days.
Meet The Feebles
(1989) My favorite Peter Jackson film is a Muppet Show parody where the Muppets have the full human range of pathological emotions and disgusting bodily functions.
Inception
(2010) The pace is too fast and there's too much fighting, but I love the script. Apparently, the best way to make an idea-heavy sci-fi film about not knowing what's real, is not to adapt a Philip K Dick novel but to write something original. Inception barely scratches the surface of the most powerful technology I can imagine, time-contracted virtual reality.
The Road Warrior
(1981) Titled Mad Max 2 outside of America, this is the clearest example of a sequel that's better than the original. Also it's a rare Mel Gibson film in which his character is not getting revenge for a murdered family member.
Ghost World
(2001) Thora Birch plays my favorite female movie character, and I love the ending.
Welcome to the Dollhouse
(1995) Of the many films about the American public school experience, this is the only one that gets it right (except maybe Elephant, which I haven't seen yet).
The Doom Generation
(1995) Asian-American director Gregg Araki combines genres in a way that's normal in Asian films but that most Americans have not yet learned to appreciate. There's over-the-top violence, hot sex, silly comedy, and serious drama all mixed together.
Dishonored
(1931) The best of seven films Marlene Dietrich made with director Josef von Sternberg.
A Fistful of Dollars
(1964) My second favorite Sergio Leone film because it's tighter and grittier than any of the others. His later films are epic and beautiful, but clean and uninspired.
Being There
(1979) In the most realistic film about American politics, Peter Sellers plays a mildly retarded man who becomes extremely powerful by being familiar with television and making vague statements on which people project deep meaning.
Life of Brian
(1979) Holy Grail is the funniest Monty Python film, Meaning of Life is the most offensive, but this one is easily the best, with a great story and a great ending.
Diva
(1981) Stylish French action/art film, with a great soundtrack.
My Mother's Castle
(1990) Another one of my favorite French films, the sequel to My Father's Glory, which was good but not this good.
Grosse Point Blank
(1997) No other American film does such a good job of merging comedy with serious violence. My favorite bit: the look on Jeremy Piven's face, after he's seen John Cusack kill a brutal assassin and helped him dispose of the body, when they sit at the bar and Cusack orders a club soda.
The Saragossa Manuscript
(1965) Polish film convincingly set in old Spain, in black and white yet bursting with life, with lots of beautiful women and human skulls, and a trippy plot of stories within stories, at one point nested five deep.
The Terminator
(1984) I don't like any of the sequels. Of course they have better special effects, but the original has a much better story.
They Live
(1988) Paranoid cult favorite, featuring the best fight scene in history, in which two characters played by pro wrestlers fight over whether one of them is going to have to put on sunglasses that show that modern civilization is an illusion created by parasitic space aliens.
The Truman Show
(1998) A guy figures out that his whole reality is fabricated and tries to escape. I like to think his name was chosen to suggest that we're all in The Human Show.
The Innocents
(1961) Classic horror film, slow-paced, atmospheric, and beautifully shot. The script was adapted from Henry James's The Turn of the Screw, largely by Truman Capote, and it keeps the source's ambiguity about whether a nervous governess is seeing real ghosts or going insane.
The War of The Roses
(1989) I've read a lot of gothic literature. Tim Burton is gothic lite, and this is the real deal. The two protagonists meet in a graveyard, die in a falling chandelier, and in between we see selfishness, revenge, sex, stairways, attics, and beautiful red and blue filters. In my favorite pair of shots, we see Michael Douglas's deathlike face looking down from a small high window of the house, and then Kathleen Turner's identical face at another window.
Go
(1999) A funny, complex action-crime movie told from multiple perspectives. I like it a bit better than Pulp Fiction -- it's less epic but more human.
Pulp Fiction
(1994) I don't like Quentin Tarantino's dialogue. But this is radical and important for its creativity with storytelling. Bruce Willis has just killed John Travolta, you think his story is over, and then Marcellus walks in front of his car and the plot goes off on the wildest tangent before or since. Also, I can't think of any other action-comedy where a bystander gets hit in a gun battle.
Night of the Hunter
(1955) The most beautiful black and white film.
Duel
(1971) Steven Spielberg's debut, and maybe his only film without anything sappy. In a story by Richard Matheson, Dennis Weaver drives a little car across the desolate and hostile American southwest, chased by a killer truck.
Airplane
(1980) If you know the difference between social laughter and genuine spontaneous laughter, this is unlikely to be surpassed as the funniest film of all time.
Hard Boiled
(1992) John Woo's Hong Kong films were the biggest breath of fresh air in the gunfight genre since Sergio Leone. One of my favorite things about Asian cinema is how they mix intense violence with playfulness and innocence, like the bit where the hero, fighting in a hospital, puts cotton in babies' ears so they aren't disturbed by the gunfire. Woo is also a great technical innovator. He may have been the first director to use a variable-speed camera to switch in and out of slow motion in the same shot.
The Chronicles of Riddick
(1999) My favorite Star Wars film. What I mean is, it's space opera on the surface, fantasy in the center, and it's not hard to do it better than George Lucas.
Runaway Train
(1985) Bleak, existential, cheesy action film with great acting.
Chinese Torture Chamber Story
(1994) One scene in this film, a flying kung-fu porn hybrid, has become famous on the internet, but the entire film is sexy and entertaining. I saw it on a big screen at the Seattle Film Festival.
Freddy Got Fingered
(2001) Okay, this is nowhere near one of the greatest films of all time. What I'm doing here at the bottom of the list is merging "best" with "most underrated". This is considered one of the worst films, but I found it totally enjoyable, and even inspiring. Most people just didn't get it.