The following list showcases 50 of the most groundbreaking and influential experimental films of all time, spanning various eras and styles.
There is so set order, just a bunch of ones I think everyone should check out.
- Un Chien Andalou (1929) - Luis Buñuel and Salvador Dalí
- Meshes of the Afternoon (1943) - Maya Deren and Alexander Hammid
- Entr’acte (1924) - René Clair
- Man with a Movie Camera (1929) - Dziga Vertov
- L’Age d’Or (1930) - Luis Buñuel
- A Movie (1958) - Bruce Conner
- Wavelength (1967) - Michael Snow
- Dog Star Man (1964) - Stan Brakhage
- The Blood of a Poet (1930) - Jean Cocteau
- Scorpio Rising (1963) - Kenneth Anger
- Inauguration of the Pleasure Dome (1954) - Kenneth Anger
- Flaming Creatures (1963) - Jack Smith
- Rose Hobart (1936) - Joseph Cornell
- Mothlight (1963) - Stan Brakhage
- La Jetée (1962) - Chris Marker
- Fuses (1964) - Carolee Schneemann
- The Dante Quartet (1987) - Stan Brakhage
- Line Describing a Cone (1973) - Anthony McCall
- Light Is Waiting (2007) - Michael Snow
- The Flicker (1966) - Tony Conrad
- Ballet Mécanique (1924) - Fernand Léger
- The Seashell and the Clergyman (1928) - Germaine Dulac
- Anemic Cinema (1926) - Marcel Duchamp
- Berlin: Symphony of a Great City (1927) - Walter Ruttmann
- Emak Bakia (1926) - Man Ray
- Ritual in Transfigured Time (1946) - Maya Deren
- At Land (1944) - Maya Deren
- A Study in Choreography for Camera (1945) - Maya Deren
- The Very Eye of Night (1958) - Maya Deren
- Window Water Baby Moving (1959) - Stan Brakhage
- Bridges-Go-Round (1958) - Shirley Clarke
- Serene Velocity (1970) - Ernie Gehr
- Zorns Lemma (1970) - Hollis Frampton
- The Act of Seeing with One’s Own Eyes (1971) - Stan Brakhage
- The Girl Chewing Gum (1976) - John Smith
- Report (1967) - Bruce Conner
- Reassemblage (1982) - Trinh T. Minh-ha
- Tongues Untied (1989) - Marlon Riggs
- Handsworth Songs (1986) - Black Audio Film Collective
- Symbiopsychotaxiplasm: Take One (1968) - William Greaves
- The Clock (2010) - Christian Marclay
- The Grand Bizarre (2018) - Jodie Mack
- Leviathan (2012) - Lucien Castaing-Taylor and Véréna Paravel
- Sans Soleil (1983) - Chris Marker
- Decasia (2002) - Bill Morrison
- Blue (1993) - Derek Jarman
- Last Year at Marienbad (1961) - Alain Resnais
- Persona (1966) - Ingmar Bergman
- Tetsuo: The Iron Man (1989) - Shinya Tsukamoto
- Eraserhead (1977) - David Lynch
The rest of the article answers that question.