My second favorite “Wild, Wild, Country”, but it was mentioned already at the top of the first list. I enjoy it as a cautionary tale, but I also unironically find it an inspiring tale of building, even if it turns out to bad.
My favorite documentary is “The Barkley Marathons, the race that eats it’s young”
I return to it at least once a year, and while the root of the story - watching people attempt the impossible is certainly inspiring, I find its moral themes are what I appreciate about it the most. The idea of competition as a collective activity, that everyone wants to win, but also everyone wants to see others win their own race, that there’s something about the way that it advances our understanding of humanity that is more important than individual success.
Then also - that your race is yours alone, and that the most important victory is the one you define for yourself. There are people who finish only one or three laps of the five lap marathon, and that failure is a greater achievement than most people will ever know, and they clearly see it that way, there’s near no shame in anyone’s performance and people are clearly defining success for themselves, mostly clearly beyond what anyone else would define it for them. And finally, it’s kind of a throwaway line, but one of the runners says “I think most people could use more pain in their lives.” And it made me realize that often, when enduring hardship, rather than turning away from it, finding ways to challenge myself on my terms is a healthier approach to stress than “relaxing”.