I just saw Comedian, the documentary about Jerry Seinfeld starting from scratch with his stand-up routine. It's very good, but not for the reasons I thought. I was expecting it to be funny: Jerry Seinfeld doing standup. Of course, it is funny, but rather than mostly being comedy, it is mostly about comedy, and about achievement, personal goals, and fulfillment. I found it very thought-provoking.
For example, in one scene, Seinfeld is talking to Garry Shandling about being on the Tonight Show, and whether Johnny Carson "called them over" (after a comedian did his stand up act, sometimes Johnny would invite them to sit down in the guest chair and chat a bit, and sometimes he wouldn't). You'd think that for a stand up comedian, the pinnacle of success would be to appear on the Tonight Show. But of course, it turns out that even after reaching that pinnacle, there are more ways to torture yourself about whether you are truly successful or not.