Fritz The Cat (1972, comedy and animation)

Not only is he animated, he's x-rated! This kitty is definitely not for the kiddies - Fritz does, indeed, have the dubious distinction of being the very first x-rated cartoon. A real tomcat in every sense of the word, Fritz is a college dropout who pussyfoots his way through a wild world of sex and drugs, 60s counterculture, and he even meets up with the Black Panthers and the Hell's Angels! Fritz the Cat is based upon the comic books by Robert Crumb, but he disliked the movie so much he sued to have his name taken off the credits. (A sequel, The Nine Lives of Fritz the Cat, was released in 1974.)

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