When I was a kid, I really liked the "Making of Star Wars" and similar documentaries that gave behind-the-scenes looks at the production of movies. These days, the "Making of ..." pieces are really just ads for the movies, usually being released before the movie itself.
But we have DVD commentary tracks. That's my favorite part of owning a DVD player: being able to hear commentary from the directors, producers, writers, and actors in movies. A lot of what they say reminds me of software development. My favorite parts are when they discuss what they would have done if they had more time and money, and make their complaints about stuff that wound up in the movie but they really don't like.
(By the way, if you liked the movie Fight Club, then you've got to listen to the commentary tracks on the DVD. Best commentary I've heard.)
I also enjoy "Inside the Actor's Studio" on the Bravo channel. Hearing actors talk about their craft, how they learned it, and how they continue to study it inspires me to continue improving my knowledge of my craft.
Commentary from software developers about their projects would not be as entertaining, but I wish we had such a thing. "The Making of Windows", as told by its developers, would certainly have some interesting bits.