20. Fear and Loathing in Las Vegas (1998)
Directed by: Terry Gilliam
So…drugs, right? Based on Hunter S. Thompson’s 1971 novel of the same title, Fear and Loathing stars Johnny Depp and Benicio del Toro as Raoul Duke and Dr. Gonzo, respectively. The pair is heading to Sin City, speeding through the Nevada desert, under the influence of mescaline. From there, the film is series a bizarre hallucinations seen through the eyes of Duke. So, we jump from hotel room to hotel room, all of the action a blur of what is happening and what really isn’t. Throughout the course of the film, Duke and/or Gonzo ingest the following drugs: mescaline, sunshine acid, diethyl ether, LSD, cocaine, and adenochrome (probably more). Duke – who is a Thompson stand-in – is supposed to be writing an article before heading back to Los Angeles, but tends to get sidetracked quite a bit. In addition to the laundry list of drugs, Gilliam also inserted an obscene list of quality actors in his film: Tobey Maguire, Ellen Barkin, Gary Busey, Chrstina Ricci, Mark Harmon, Cameron Diaz, Katherine Helmond, Christopher Meloni, and Harry Dean Stanton. Early in the film’s development, Jack Nicholson and Marlon Brando were originally considered for the leads, but time passed a little too much for that to be reasonable, as well as both Scorsese and Oliver Stone one time trying to adapt the novel. In the end, the film was a box office failure, only recouping a little over 50% of its budget. But, just as with plenty of other films on this list, it found second life on DVD, thanks to the “comfort of your own home” pastiche, which could involve any number of substances beyond popcorn and overpriced soda. So the film lives on in its hazy, drug-soaked grandeur, all the way through bat country and beyond.
19. Teorema (1968)
Directed by: Pier Paolo Pasolini
Ever the artist, Pasolini’s filmography is one of the more engaging ones in film history, spanning the chasm between the aggressively graphic horror film Salo all the way to probably the best Bible adaptation of all time with The Gospel According to St. Matthew. At the core of his efforts was a desire to challenge viewers into seeing things from different perspectives. Teorema centers on a rich Italian family and the sudden appearance of a man simply referred to as “The Visitor,” played by Terence Stamp. He seems without need – he asks nothing from the family, but provides everything each of the members of the household needs. He keeps the maid from committing suicide. He offers friendship to the frightened son, filling him with confidence. He offers an emotional outlet to the overprotected daughter, forcing her internal maturity. He provides an outlet for the bored housewife. He cares for the father, who is slowly dying. But within all this support and love is sexual relations. With all of them. Every one. And just as quickly as he swoops in, he leaves without reason. His departure forces the hand of every person: the maid returns home to her village, the son leaves to become an artist, the daughter slips into a catatonic state, the mother starts sleeping with any young man who looks like The Visitor, and the father strips himself of everything: business, money…even clothes. Pasolini’s ambiguous film doesn’t offer so much in terms of confusing action or bewildering narrative structure; it’s pretty straightforward. Bu the interpretation of the film is baffling. It could be a commentary of sexuality as a whole, stemming from Pasolini’s struggle with his own identity. It has hints of a political criticism against the Italian state, Pasolini being a lifelong Communist. Teorema translates to “Theorem” in Italian that, while typically a mathematic term, can be applied in the sense that Teorema holds onto a pretty rigid formulaic approach to the character development. At the hands of The Visitor, each character goes through the same changes, beginning with their desire to be with him to their need to expose themselves to him to their psychological change as a result of his presence. The film served as inspiration for another foreign language offering, Takashi Miike’s 2001 film Visitor Q, which takes the same approach, but veers much further into the horror genre.
18. Brazil (1985)
Directed by: Terry Gilliam
When Gilliam finishes projects, they tend to lean a little surreal, but have some sort of clear point to them, a la The Fisher King and 12 Monkeys. But – as we’ve seen twice on this list already – when he goes full-on crazy, it’s a sight to see. His first crazy film that was also a critical success was 1985’s Brazil, a variation on George Orwell’s Nineteen Eighty-Four, but with a lot more humor and silliness. Sam Lowry (Jonathan Pryce) is looking high and low for a woman he only sees in his dreams while working at a dead end job. His dystopian world is run by ridiculous machines, forcing a human dependence, despite their obvious inconsistencies. A fly gets jammed in a printer at his office, causing a chain reaction that results in the death of an innocent cobbler who shares the name with a known terrorist. Sam visits his widow, only to meet the neighbor Jill (Kim Greist), a dead giveaway for the damsel in distress from his fantasies. So, while larger, bureaucratic prejudices are occurring, Sam wants nothing more than to learn about Jill, getting himself deeper and deeper into a corrupt conspiracy he was not prepared for. Sam and Jill travel in and out of air ducts, only to result in Sam’s apprehension at the hands of the government, charging him with treason and strapping him to a chair in a round room with a masked torturer. Gilliam’s film weaves in and out of this futuristic madhouse, keeping his audience guessing about what is real and what is a daydream, all the way to the very end. The film boasts as wonderful cast, including Robert De Niro, Ian Holm, Bob Hoskins, and Michael Palin, who plays the eventual torturer Jack Lint, a part De Niro wanted, but Gilliam had already promised to Palin. Brazil grabbed two Oscar nominations for At Direction (of course) and, surprisingly, Original Screenplay, thanks to Gilliam and his collaborators Charles McKeown and Tom Stoppard (eventual winner for Shakespeare in Love). Of all Gilliam’s trips into the surreal realm, Brazil is certainly the best, maintaining a personality that fits into a perfectly designed world of simultaneous misery and whimsy. It’s crazy, for sure. But beneath that crazy is a sentiment that isn’t normally seen in films of this nature.
17. Lost Highway (1997)
Directed by: David Lynch
David Lynch is such a modern master of psychological movie dreamscapes that even his missteps are incredibly memorable. Enter Lost Highway, the story of a jazz saxophonist named Fred (Bill Pullman) who begins to experience outlandish things happen to him. After he receives a mysterious message (“Dick Laurent is dead”) and package at his home containing a videotape of his house, Fred and his wife Renee (Patricia Arquette) attend a party where Fred had an unsettling encounter with a mystery man (Robert Blake), who he is told is a friend of Dick Laurent. The next morning, another tape arrives, showing Fred killing Renee, at which point he is arrested and put on death row. One morning during cell checks, Fred has miraculously transformed into Pete Dayton (Balthazar Getty), an innocent auto mechanic. So, he’s released, where he returns to his job and begins an unlikely partnership with a local gangster named Mr. Eddy (Robert Loggia). We follow Pete as he begins an affair with Mr. Eddy’s mistress (also played by Patricia Arquette), until he eventually transforms back into Fred. The interwoven plotlines and mistaken identities are shuffled so much in this film, even more so than what’s normal for Lynch. Blake’s appearance as the mystery man come at inexplicable moments and shifts the film into something that hinges on ethereal surrealism to full on paranoid exposition (or lack thereof). Explanations are in short supply; while Lynch’s other more accomplished films don’t necessary answer the questions they pose, they at least provide a strong throughline of story and character development that the audience can grab on to. Lost Highway was Lynch’s follow-up to his ill-fated Twin Peaks movie, a continuation of his mindbending, but critically acclaimed TV series. Lost Highway featured the final film performances from Blake, Richard Pryor, and Jack Nance, as well as the film debut of Marilyn Manson. In a filmography twisted narratives, Lost Highway sits nowhere near the top in terms of quality, but creeps into the cult canon for its inexplicable “story.”
16. The Exterminating Angel (1962)
Directed by: Luis Buñuel
Ever been to a dinner party you feel like never ends? Well, at least it did. In The Exterminating Angel, a dinner party at the mansion of Señor Edmundo Nobile and his wife Lucia (Enrique Rambal and Lucy Gallardo) is going fine, until all the servants suddenly decide to leave. The party continues, but when normal parties would end and people would leave, all the guests instead end up sleeping on the floor. When they awake, it is apparent that they can’t leave the music room, where the night before they sat and listened to a sonata. They aren’t locked in – there are no doors holding them back. They just can’t leave. Hours turn into days, days turn into weeks. They begin to fight. One of the guests dies and they shove him into a cabinet. Two of the other guests kill themselves. Only one guest seems to stay calm through the entire ordeal – a logical doctor who tries to calm everyone. Eventually, they begin to blame each other, eventually settling on trying to reenact the events that occurred just before they believe their collective stasis began. Buñuel’s history of surrealist social critique is well defined here, despite the somewhat incomprehensible concept. At one stage, livestock inexplicably enter the room, only to serve as space eaters. Whether Buñuel is criticizing the bourgeoisie lifestyle, the Catholic Church, or both, his satire is cutting and whimsical. Don’t watch The Exterminating Angel as a mystery or a heavy drama; it’s a comedy of social errors, more than anything.
15. Dune (1980)
Directed by: David Lynch
Disclaimer: I’ve seen Dune once. I wouldn’t wish it on my worst enemy. That being said, David Lynch’s epic misfire fits this list’s definition in so many ways. Based on Frank Herbert’s mammoth novel of the same name, Dune is a 2+ hour amalgam on science fiction and fantasy that makes next to no sense. It focuses on a Duke’s son named Paul (Kyle MacLachlan) as he leads an army of desert people against the evil emperor after his father is assassinated. That is simplest explanation possible. The entire universe is searching for a space called melange that extends your life and expands your consciousness, and various parties are sending all they can to battle sandworms and giant floating organs and Sting. Herbert’s novel is so overstuffed that any attempts to cram every theme he covers into one tight film is impossible. Lynch claims his creative vision was compromised by the influence of producers and financiers, to the point that he distanced himself from the finished product. This exceptionally confusing movie is still hailed as one of the greatest conceptual failures of all time, and for good reason. The plot makes no sense. The special effects are erratic. But, despite there being next to no redeeming qualities about the film, for the purpose of this list, it really is a must see.
14. Crash (1994)
Directed by: David Cronenberg
Eight years before the other Crash won one of the most disputed Best Picture Oscars of all time, David Cronenberg delivered a much more unsettling Crash based on J.G. Ballard’s 1973 novel of the same name. Most Cronenberg movies are too far into the horror genre to be included in this list, but this NC-17 rated thriller stays just far enough away from it to fit. A film producer named James (James Spader) and his wife Catherine (Deborah Kara Unger) have an open marriage, only titillated by the discussions of their other partners. One night, James suffers through a horrific car accident, killing the other driver, but leaving the driver’s wife Helen (Holly Hunter) alive. While both James and Helen lie there, she exposes herself to him, leading to the discovery of a shared fetish of insurmountable proportions. All of Helen’s sexual encounters have occurred in cars; she and James begin an affair, leading them to an underground cult of people with obsessions with car accidents and their ability to arouse desire. James begins compulsively trying to relive his accident, watching car safety videos and going to accident sites. He meets Gabrielle (Rosanna Arquette), a woman whose legs are in braces, but who has a strange scar on the back of her leg that, well, stands in for her vagina. The leader of the underground movement Vaughan (Elias Koteas) is trying to prove that the car crashes are actually beautiful events that give birth to an intense sexualization that is impossible to find any other place. Oddly, this twisted endeavor eventually bring James and wife closer together, as she is eventually drawn into the practice. Cronenberg and body horror go hand-in-hand, and much of his work tends to veer into the diagnosis of human sexuality, as well. Crash won the Special Jury Prize at Cannes in 1996, though it was nominated for the Palme d’Or and, while an extremely divisive film, won great praise from many critics, including Roger Ebert, who stated it’s “like a porno movie made by a computer…I admired it, although I cannot say I ‘liked’ it.” And that’s really a good statement for many of the films on this list. For every Dune or Southland Tales, there’s a Crash which is every bit as gut-wrenching and bewildering, but in a way that is pushing the boundaries in a way that feels organic and interesting.
13. The Fountain (2006)
Directed by: Darren Aronofsky
While Aronofsky has slowly moved into more commercial fare (I haven’t seen Noah yet), the majority of his career has been spent churning out small art films that degrade, confuse, or blow away viewers. His first offering that took on a good size budget was The Fountain, which he also wrote with Ari Handel. The film has three parallel narratives: 1) a scientist named Tom searching for a cure for his wife Izzi’s cancer, 2) a Spanish conquistador named Tomás searching for the Tree of Life for Queen Isabel, and 3) Tommy the astronaut flying around in a globe with the Tree of Life and speaking with ghosts of Izzi from the first scenario. The two leads in each story are played by Hugh Jackman and Rachel Weisz. The three stories interweave, not following a chronological structure, though each is separated by five centuries of time. Scenario 1 is the main plot, with scenario 2 being a story Izzi is writing to her husband, and scenario 3 being a story they are telling to one another while looking into the stars. There is no definitive answer as to how the stories are connected, since the Tree of Life’s inclusion possibly insinuates that these stories all involve the same people: Tomás=Tom=Tommy and Isabel=Izzi. Aronofsky’s college roommate Handel would eventually become a Ph.D. in neuroscience and helped build the story with Aronofsky, piecing together a larger story about how we, as humans, deal with the onset of death and the neverending war with mortality. What resulted was The Fountain, a big film about big concepts that, while all the pieces don’t necessarily fit together easily (or aren’t supposed to), still leaves an imprint on your psyche. Trying to figure The Fountain out takes away from its impact. If anything, let it wash over you like ocean waves and take in the incredible weight of the narrative. For me personally, The Fountain is never a film I would say I love or even like that much. But, every time I think back on it, it takes my breath away for a moment.
12. Synecdoche, New York (2008)
Directed by: Charlie Kaufman
After years of providing other talented directors with mind-bending, brilliant scripts, Charlie Kaufman finally decided to get in the director’s chair himself, making a movie out of easily his most complicated screenplay. Starring the late Philip Seymour Hoffman in one of his finest performances, Synecdoche, New York centers on Caden Cotard (Hoffman), a theater director who suffers from chronic pain discomfort and is losing his wife and daughter, as they move to Berlin. Unexpectedly, Caden then receives a Fellowship, providing him with the financial backing to create any art project he wants to. He decides to use it to put on an incredibly honest play, the scope of which is enormous. He pulls together an ensemble in a warehouse in Manhattan, where he reconstructs the larger Manhattan and instructs his cast to simply act out what they would normally do in their daily lives. Caden slowly begins to cast more and more people, all of which are stand-ins for people in his own life. As his personal life crumbles and his health gets worse and worse, Caden realizes that, in order to achieve true greatness, he would also need to cast himself. The blur between the world outside the warehouse and the play itself gets increasingly hazier, as his vision is compromised over and over, thanks to his inability to recognize the differences between reality and his production. Kaufman’s film is one of the few movies that goes beyond a surface level diagnosis of the craft and more into the psychoanalysis of how theater and the art form can both enhance and destroy the human existence. It’s never clear what Caden is suffering from that is causing his body to shut down, but there’s a good chance that it’s just a psychological block that refuses to let him get beyond his own head and begin to understand the world around him. The biggest theme the film tackles is human perception. When casting someone to play your wife, how do you write the part? There’s no reasonable way for you to be accurate, because your wife is a character in your eyes that is wholly different than her character in her mother’s eyes and her own character in her own eyes. Synecdoche, New York is heavy, to say the least. But when Caden diagnoses the world around him and decides to make it his own personal dollhouse, he doesn’t take into consideration that his vision of these people is misguided. Kaufman’s film is easily one of the most philosophically trying on the list, but the experience of watching Hoffman in this role and what he does with Kaufman’s brilliant script is nothing short of brilliant and worth the headache you may feel afterward.
11. Holy Mountain (1973)
Directed by: Alejandro Jodorowsky
An avant-garde Mexican-American film produced by The Beatles manager and partially funded by John Lennon and Yoko Ono? Sign me up! Directed by surrealist master Alejandro Jodorowsky, The Holy Mountain begins with a man (who looks suspiciously like Jesus) played by Horacio Salinas lying on the ground, covered in flies. He is referred to as the thief and he and his friend – a footless dwarf – head into town to make money, while residents begin to fashion crucifixes and things with his face, due to his resemblance of Jesus. He gets into a fight with a priest, eats the face off a wax statue of himself, and ascends up a tower to find out where a bag of gold that has been dropped came from. There, he meets an alchemist (played by Jodorowsky) and his assistant. He defecates into a container, which the alchemist turns into gold, only to see the thief take the gold and use it to smash a mirror after seeing himself. He become the alchemist’s apprentice. They invite a group of seven other people, each personifying one of the planets, to join them on a journey, making ten travelers. They travel to Lotus Island to find the secret of immortality, but along the way engage in a number of strange death/re-birth rituals. Sure enough, they get there, only to find a number of other travelers who have gotten sidetracked by drugs, poetry, and other physical needs. They meet the immortals – cloaked people with no faces – just before the close of the film, which I won’t spoil, due to its “out-of-left-field” approach. Jodorowsky has not made a ton of feature films (seven in all), but he is still widely recognized as one of the most interesting filmmakers of all time, thanks to his unorthodox storytelling style and seeming lack of closure in many of his films. Holy Mountain takes influences from a number of places. Many of the characters (including the thief) are based on Tarot cards. The original basis is Saint John of the Cross’ treatise Ascent of Mount Carmel, which is basically a how-to book on asceticism, or the avoidance of worldly pleasures, in an attempt to gain a union with Christ. In addition, Jodorowsky took cues from René Daumal’s novel Mount Analogue, which is a bizarre story abut the ascent of an inaccessible mountain. Needless to say, Jodorowsky’s film is a mind trip, thanks to the broken structure and drug-influenced imagery and storytelling. It’s a spiritual journey up a mountain, yes. But it’s also just a movie.