Fritz the Cat

You fans of animation out there may or may not be familier with this guy-

If not, and you dont mind a bit of... irreverence, Fritz here played a pretty big part in the history of modern animation as the first X rated animated film releasing back in 1972 to hefty controversy, ultimately becoming a huge financial success to the studio. The film takes a hard uncensored look at modern life in the late 60's in America, portraying things like swinger culture, drugs and racism in a hard and characterized light.

While the character started his life in a comic strip in 1965 created by Robert Crumb, the film was created by Ralph Bakshi as his first venture into studio animation. 

Ralph Bakshi is kind of a lunatic and I love him, having his hand in a number of off the wall and maddeningly creative animated projects and movies. 

The film is pretty easy to find but i warn you, despite being 45 years old this cartoon movie has lost none of its explicit edge. Not for the kiddos XD