I recently watched two films directed by Vincente Minnelli and starring Kirk Douglas which were about filmmaking. They’re both on Warner Archive Blu-rays.
The first, The Bad and the Beautiful (1952) stars Douglas as a producer who screws over a writer, director and actor. Most of the film takes place in flashbacks. The great Gloria Grahame won an Oscar for a role in which she only had nine minutes of screen time. There’s lots of speculation on who the main characters are based on. It’s an entertaining gossipy film about the sleazy side of Hollywood and is well worth seeing.
Two Weeksi in Another Town (1962) isn’t a sequel. This time, Douglas plays an actor who is down on his luck and gets a role in a film shot in Rome. Hollywood’s underbelly is on display again but this one isn’t quite as good. One cool reference to the earlier film is when they show a clip of it; they show Douglas’s character in this one as an actor in the first one.
Some other Hollywood films about filmmaking that I like (and I’ll probably add to this)
Ed Wood (1994) is Tim Burton’s excellent film about the director of some of the worst films ever. It smartly is shot in black and white and focuses on three of his films. What makes it work is that Wood doesn’t realize he is terrible; he actually thinks he’s good.
Boogie Nights (1997) is Paul Thomas Anderson’s ensemble film about the porno film industry.
Singin’ in the Rain (1952) is a musical about the transition from silent films to sound films. One of the best musical films ever.
What Price Hollywood? (1932) directed by George Cukor follows the rise of a waitress to stardom
Bombshell (1933) directed by Victor Fleming is a comedy about a movie star played by Jean Harlow
The Last Command (1928) a silent film directed by Josef von Sternberg about a former Russian leader reduced to a movie extra.
Sad! 