When it comes to surreal cinema I´ll have to recommend the master of that sort of filmmaking; Louis Bunuel. Here are some good films of his:
The Phantom of Liberty (1974). The funniest film I´ve ever seen. Tremendous entertainment value. Bunuel also abuses narrative conventions here quite cleverly.
The Discreet Charm of the Bourgeoisie (1972). This one is a great introduction to Bunuel. It´s more accessible than many of his films, but also just really good.
The Exterminating Angel (1962). Not sure if I recommend this as a first Bunuel film, but a personal favourite of mine. Really weird and funny. Some find it a bit disturbing.
Beauty of the Day (1967). Not Bunuel´s most surreal but a very good and somewhat accessible film. It´s about a bored middle- class housewife who decides to become a prostitute at a classy brothel in Paris. My first introduction to that eccentric visionary filmmaker.
So, other films I recommend which are surreal/weird are:
El topo (1970). One of my favourite films. It´s a surreal, stylish and violent western full of some of the oddest moments I´ve seen ever in a film. The director Alejandro Jodorowsky also made "Santa Sangre" and "Holy Mountain", which have been mentioned above. I like those films as well, but I think this is his best.
Last year at Marienbad (1961). This French film is the most visually stunning films I´ve ever seen. I´ve never before or since seen such impressive cinematography. The storyline is very vague and ambiguous, and can be interpreted in many different ways. It takes place in a villa somewhere in the French countryside where a bunch of rich people are passing the time by gambling, hunting, watching play´s etc. We follow this man who the entire film is trying to convince this woman that they have met before, but she does not remember him. He, however, is very determined in making her remember their earlier meeting, and follows her around in an almost stalker- like fashion. As the film progresses we don´t know whether what´s taking place on the screen is the past or present, reality or imagination. A truly unique film and an important work in cinema history.
Werckmeister Harmonies (2000). My personal favourite film (hence, my user name
) I fully understand that this is not a film of everyones taste and I don´t really recommend it to everyone, but for those who are able to enjoy this film on it´s own terms, you are in for one of the most unique and rewarding cinematic experience available. This is a deeply philosophical film with some really impressive cinematography (the long takes sometimes try the patience of some viewers). The film is made by the Hungarian director Béla Tarr, one of the most respected filmmakers of our times. The film is all at once dark, bleak, beautiful, mesmerizing and full of some really odd and eccentric sense of humor.
Daisies (1966). A brilliant little film from the Czech New wave. It´s both a pioneering work of modernist and feminist cinema. It centers on two girls who decide to show society the finger by engaging in strange and eccentric pranks, and generally living a marginal lifestyle according to a rather nihilistic world view. A very playful and entertaining film. Very different from the stereotype most people have of Eastern- European cinema.