Pink Flamingos (John Waters, 1972)
"An exercise in poor taste" - Divine gets challenged, and does not chicken out. "Pink Flamingoes" is a classic of transgressive cinema.
https://www.imdb.com/title/tt0069089/
https://de.wikipedia.org/wiki/Pink_Flamingos
Birdemic: Shock and Terror (James Nguyen, 2010)
Mostly it's "Troll 2" (1990) vs. "Manos: The Hands of Fate" (1966) vs. "Plan 9 from Outer Space" (1959) for the distinction of being the worst movie ever made - but then there's "Birdemic: Shock and Terror". It certainly succeeds in one regard: the title perfectly describes the impression the movie leaves behind. Shock and Terror.
https://www.imdb.com/title/tt1316037/
https://de.wikipedia.org/wiki/Birdemic:_Shock_and_Terror
A serbian film (Srdjan Spasojević, 2010)
Often cited to be the most violent and most uncomfortable movie ever made, "A Serbian Film" is far from being cheap or stupid - but, yes, it breaks a taboo. In fact lots of. Not everyone might get the message, in fact not everyone would even ask for the message in "A Serbian Film", but it's meant to be controversial, and it certainly succeeds at being so.
https://www.imdb.com/title/tt1273235/
https://de.wikipedia.org/wiki/A_Serbian_Film
Un chien andalou ("Ein andalusischer Hund", Luis Bunuel, Salvador Dali, 1929)
The grandmother of all transgressive films. A short experimental by two renowned artists that (in)famously features a cut through the eye, along with other disturbing imagery.
https://www.imdb.com/title/tt0020530/
https://de.wikipedia.org/wiki/Ein_andalusischer_Hund
Nekromantik (Jörg Buttgereit, 1987)
German low-budget movie about the morbid existence of a necrophilist. A very gritty, lo-fi, and melancholic production.
https://www.imdb.com/title/tt0093608/
https://de.wikipedia.org/wiki/Nekromantik
Der Weg nach Eden (Robert-Adrian Pejo, 1995)
Portrait of a mortician's work. Extremely disturbing, and deeply moving at the same time.
https://www.imdb.com/title/tt0114904/
Salo o le 120 giornate di sodoma ("Die 120 Tage von Sodom", P. P. Pasolini, 1975)
Artful, but extremely violent treatment and commentary on fascism and Nazi occupation in Italy.
https://www.imdb.com/title/tt0073650/
https://de.wikipedia.org/wiki/Die_120_Tage_von_Sodom_(Film)
Lo squartatore di New York ("Der New York Ripper", Lucio Fulci, 1982)
Probably the sleaziest giallo ever made, and a very gory one.
https://www.imdb.com/title/tt0084719/
https://de.wikipedia.org/wiki/Der_New_York_Ripper
Cannibal Holocaust ("Nackt und zerfleischt", Ruggero Deodato, 1980)
The ultimate cannibal shocker, and one of the best found-footage films.
https://www.imdb.com/title/tt0078935/
https://de.wikipedia.org/wiki/Nackt_und_zerfleischt
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