1930: L'age d'Or

The follow-up to Chien Andalou is four times as long, has some sound (apparently added in postproduction) and doesn't seem quite as fresh as its predecessor to me. Also, you can't shock anyone nowadays with allusions to masturbation and fellatio. Fun fact (if it is a fact): "The film cost a million francs to produce and was financed by the nobleman Vicomte Charles de Noailles, who beginning in 1928 commissioned a film every year for the birthday of his wife Marie-Laure de Noailles." (6)