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Fritz the Cat (1972)

Directed by Ralph Bakshi. Animated film about Fritz, a college-aged feline wandering the hippie-era streets of New York in search of political, sexual and chemical experiences. 90 min. ; Credits and other information from the Internet Movie Database
The first animated film to receive an "X" rating in the US, promoted with the tagline "He's X Rated and Animated!" Although it was given an "X" rating due to its strong sexual content and hard drug references and usage, the material in the film itself wasn't pornographic and the film was later released unrated on VHS and DVD.