57. The Aristocrats (2005)

One of the best documentaries about comedy ever made. A host of famous comedians, including George Carlin, Billy Connolly, Lewis Black and Sarah Silverman, give their own versions of a legendary burlesque joke that is traditionally told amongst comedians (Mostly because telling the joke properly requires descending so far into utter filth and depravity that very few comedians would dare try it on the public). On the surface level, we get scads of world-famous comedians being as filthy as they can muster, which leads to a few surprises (Bob Saget being funny, Gilbert Gottfried being a hero of free speech, Carrot Top being... Well no, Carrot Top is still shit even here).
However, it's what the film suggests between the jokes is what makes it so great, and a genuinely exciting watch for comedy lovers. It's a glorious dissertation on the cathartic joy of black humour and the much-underestimated amount of creativity it takes to use filth well. This creativity is definitely on full display here; while it's technically the same joke being told over and over, the range of takes the cast make on it makes it feel like a new joke every single time, and brings out sides to many of these comedians we never knew existed.
While it's no example of documentary craftsmanship - it sticks to a 'talking heads' style and doesn't attempt any kind of narrative structure - it also doesn't need to be. The focus is the comedians and the wierd and wonderful ways they twist the story to their own tastes and styles, and by doing so makes comedy itself the star.