9. Trumbo (2007)
Written by his son Christopher Trumbo, and based on his own letters, this documentary chronicles much of the life of Dalton Trumbo, a screenwriter (and Oscar-winner, no doubt) who found himself imprisoned and blacklisted in the 1940s under an investigation of Communism and its supposed influence in Hollywood movies. History buffs will recognise Trumbo as just one of ten screenwriters (who came to be known as "The Hollywood Ten") who refused to testify for a committee. Though this documentary isn't directly focused on the craft of screenwriting, I still think it's an essential look at the Hollywood system for anybody who's interested in how things used to work and an important tribute to an obviously wonderful screenwriter: Trumbo won two Oscars whilst blacklisted (and working under a pseudonym), and was the writer behind
Spartacus. Can you imagine how frustrating it must've been working under an alias and winning Oscars you couldn't claim?