Controversy over free speech has apparently bred some sort of genre of film in which the material focuses on trying to be offensive. There have been a substantial number of shows and movies which are teeming with violence, drug use, sex, and stereotypes, exaggerated in a way that can only serve to push the boundaries of free expression. For some reason or another, a large portion of the more salient examples of purposely offensive material appear to be animation. Perhaps it's because it's easier and less unpleasant to animate certain terrible actions, or because it makes an even stronger point to make what is sometime's regarded as a children's medium offensive. Maybe it's because you can animate physical traits that are racially insensitive ("darky" iconography, buck-toothed asians, busty women), or maybe I just noticed it because I love animation.
To start, there was the movie Salo, or 120 Days of Sodom. When it was first made, it was considered the most offensive movie of all time. It was the product of a book so full of depraved sex, even /b/tards might have a hard time reading it, and it was coupled terrible messages. Marquis DeSade, the author (from whom the word Sadism comes), was jailed for his perverseness.
Ralph Bakshi created the first X-rated animated film, Fritz the Cat. Since then, his animated films have generally not been targeted towards children. Probably the most overt example of this would be his movie Coonskin, aka Street Fight. The movie is a parody of the controversial Song of the South but is 100 times worse, full of black caricatures who occupy the roles of mob boss, preacher, exploiters of religion, exploited athlete, crazy homeless man, and pimp to name a few. There is surprisingly little controversy surrounding this film, perhaps because Bakshi made it clear from the sheer extremeness of the film that it was trying to be shocking and mock darky iconography. Here are a few clips set to the opening theme:
It's hard to say, but Bakshi may have contributed to what I can only describe as a sub-sub-genre, of black animated characters which are far from PC, made by black artists. A popular example is Aaron McGrudger's The Boondocks.
Read a Book is a parody of the schools trying to appeal to kids to get messages across.
T-Pain and other rap artists recently made this movie, called Freaknik the Musical:
Borat and Bruno are probably good, but still very contentious, examples of making stereotypes look ridiculous.
South Park has tread on this topic multiple times, and has been controversial as of late. There were a few episodes that focused on offensiveness (mostly swearing) and then the movie South Park: Bigger, Longer, and Uncut, focused on that theme. The most recent episodes (200 and 201) did not try portray the most offensive cumulation of vile images possible, but one of the most contested images of all time, that of the Muslim prophet Muhammad. The image of Muhammad, the word "Muhammad," and a speech on why media shouldn't give into intimidation by extremists (not about Muhammad), was censored by comedy central.
Recently, the Direct-to-DVD movie called The Drawn Together Movie: The Movie came out, based on the discontinued Drawn Together TV series. In the movie, the characters run around doing many disturbing things, for apparently no reason. With the help of a character that is a parody of South Park, they search for a "meaning" to accompany their perverseness, which will supposedly help them not get canceled. In the end they decide that there need not be a reason or a message behind offensive television, which is ironically a message in itself.
Some would say that these pieces are a detriment to free speech, in that they are a flagrant abuse of the right and a reason to make restrictions. In my opinion, purposely offensive films are extremely important to free speech in that they keep the boundaries pushed, and they affirm that even when this offensive material is produced, it is still harmless. Even if the films themselves don't make a point, they keep the path clear for anyone who does want to make a point using offensive methods.