I’d love some suggestions for “how the sausage is made” kinds of documentaries. I really, really liked 6 Days To Air about the South Park guys and would love to see more of those about areas of work that remain somewhat mysterious - mainly film or politics but also wrestling or sports if you want to include those too.
I’ve seen The War Room and really enjoyed it and I actually liked the FX show The Comedians, though apparently I was the only one.
Startup.com, a documentary on a (failed) online company during the dotcom boom. It’s incredibly telling how the two founders appear more like overgrown boys than serious businessmen. Overnight, the story of how “Boondock Saints” creator Troy Duffy both became Hollywood’s biggest shooting star and how he crashed to earth. Duffy gets slammed regularly by most observers, and he certainly doesn’t help himself at all. But it also started the first chips in the Weinstein brothers armor by showing how much of their mystique was mostly marketing.
Game Change is the movie version of the book Game Change about the 2008 presidential campaigns. Although it’s not technically a documentary (actors play the characters involved), it does give you insight into how the sausage is made.