One of my favorite sub-sub-genres is "Meta Movies" or movies about movie making. There are actually rather a lot of movies that fall in this category, probably because people are almost always most interested in themselves and movie makers are people, too. Most examples are fiction, from Singing in the Rain to Christopher Guest's For Your Consideration, Meta Movies use movie making as the convenient McGuffin plot driver, but, ultimately, the story was not about the movie making. In Mr. Guest's case, it's obvious that he can substitute in a dog show or a rock band with similar results.
The other class of Meta Movies is the documentary, which I personally find fascinating, but I want to distinguish this from the Behind the Scenes material you often find on a DVD's Extras menu, which are most often just random bits of interesting production trivia or short segments illuminating a particular aspect of a shoot. They don't typically have much structure or the narrative drive of a tightly edited documentary. And so I've compiled a short list of Meta Movies here that are either complete narrative documentaries or fictional treatments where the movie making is genuinely the focus of the project.
NOTE: This is not intended to be any sort of comprehensive list. Especially in the case of the fictional Meta Movies, where there are probably literally hundreds of examples. Instead, what follows is a list of some of my favorites.
Meta Movies - Documentaries
The Cutting Edge: The Magic of Movie Editing (2004)
Modern, fun, very watchable and highly recommended. There's no overall story here, so it has more of the feel of a PBS (or BBC in this case) made-for-TV documentary, but still worth a rental.
Visions of Light (1993)
Absolutely a must see documentary, although I'll admit it's not narrative: 90 minutes of interviews with famous Directors of Photography and tons of examples. Lovely pacing and historically interesting, keep a notebook nearby, because you'll see tons of movies that you'll want to rent while watching.
R2PC: Road to Park City (1999)
This is a movie about making a movie to win Sundance. Silly and somewhat self-indulgent, but still good-natured, I laughed out loud a couple of times. For example, when the director goes into B&H to rent a camera and the salesman asks him what kind of camera he wants and he says "The kind that can win Sundance." Or when he gets chased by the Steadicam operator. Or the C-47 explanation.
Overnight (2003)
Perhaps the ultimate cautionary tale for indie filmmakers about a manic, egotistical wannabe filmmaker that convinces all sorts of famous people to give him money and get involved in his film The Boondock Saints. Fascinating documentary with lots of hubris and much better than the actual movie that eventually got made.
American Movie (1999)
Unlike the egotistical jerk in Overnight, you'll be rooting for Mark Borchardt and his friends to complete their amateur horror movie. If you watch this and simply laugh at the gross incompetence and idiocy of these boys from Wisconsin, you're missing the point: They made a freakin' movie. On film. And premiered it in a movie theater. And now have a DVD. I Wish I could be that incompetent and idiotic. Really a very inspirational movie for those of us that wish we could make a movie someday.
Lost in LaMancha (2002)
Terry Gilliam documentary that was the result of a quixotic attempt to make a movie called The Man Who Killed Don Quixote. Irony abounds as the little making-of featurette becomes the primary output from the main project, which fails spectacularly after only six days. Bad planning? Bad luck? Cursed from the start? It's hard to believe so much could go so badly wrong so quickly.
I thought this Steve Martin/Eddie Murphy movie was really funny and rather underrated. It's not High Art and you won't learn anything about filmmaking from it, but you'll probably get a chuckle or two.
Full Frontal (2002)
Steven Soderbergh's meta movie about Hollywood, filmmaking and what's real (and what's not). Clever in implementation, it's actually a pretty enjoyable film that will alternately engage you and then give you a little slap in the face to remind you you are watching a movie.
Living in Oblivion (1995)
This movie doesn't hold together all the way through and the ending seems, well, arbitrary. Maybe that was the point. I liked this movie well enough and definitely recommend it, but it's not my favorite on this list.
8 1/2 (1963)
This Federico Fellini film is more about the frustrations and struggles of a famous director than about actually making a film. Trippy dream sequences, childhood angst, mid-life crisis, affairs with young mistresses and lots of odd stuff. Occasionally humorous and beautifully shot, this introspective film can be "challenging" (read: boring and confusing) for normal people (read: non-artsy-fartsy movie fans) that might be used to giant robots, explosions and linear plots based in the physical world.
Day for Night (1973)
O.K., so you are probably thinking that if I pan a Fellini Art Film, a Truffaut film has no chance, but you'd be wrong! Not only is this Francois Truffaut movie about making a movie, but Francois Truffaut plays the director in it. The plot is interesting, at times tragic, sometimes funny and ultimately really enjoyable, with a couple of twists. It has a realistic, natural feel and the background scenes that reveal the production are fascinating and seamlessly integrated. It's charmingly acted, unpretentious, not at all self indulgent or even self aware - which is really quite amazing for a meta movie! As the editor of the real movie says "It's not just a movie about cinema, it's a movie about life." This is, without question, the best meta-movie ever and is simply a good movie about any subject, winning the 1973 Academy Award for Best Foreign Film.
The Big Picture (1989)
Christopher Guest's directorial debut and worth watching for that reason alone. It's not a mockumentary, but it's got Kevin Bacon, Martin Short and a bevy of other cameos. Definitely not my favorite Guest movie and (like 8 1/2) is only peripherally about trying to make a film. Reminds me of Hollywood Shuffle in a lot of ways, but not as silly or fun. If you have a Netflix subscription, you can view this one on-demand via the Watch Now feature over a broadband connection.
The Camera Man (1928)
Buster Keaton slapstick silent film which is in the public domain and can be viewed at the fabulous Prelinger Archive right this very moment by clicking here! (duration: 67 minutes)
Hollywood Shuffle (1987)
Robert Townsend's first movie (shot on the proverbial credit card for $100k) is about one black actor's quest to break into mainstream movie rolls. Lots of cameos and hysterical short fantasy segments (Rambro, Dirty Larry, and zombie pimps to name but three), this is a truly underrated and funny movie with a heart. Not strictly about movie making, but, then again, neither is Fellini's 8 1/2, and this movie is a lot more fun. Even the trailer is hysterical (watch the trailer below or try out Amazon's VoD service and watch the whole movie for $3).
A Man with a Movie Camera (1929)
This isn't really fiction, but it's not a documentary either. To be honest, it's not about filmmaking, either and the eponymous "Man" only shows up occasionally. Oh, and it's a hoity-toity artsy-fartsy Russian Art Film, with everything that implies. It is very trippy and modern for 1929, however, and is quite surprising, really. You can watch it for free at the fabulous archive.org and then cite it the next time you need to one-up a snotty trust-fund baby film student with an obscure reference, although you should probably refer to it casually as "Dziga Vertov's Chelovek s Kinoapparatom."
Singing in the Rain (1952)
Yea, everyone knows it's got Gene Kelly and some singin' (and dancin') in the rain, but it's also got a really funny story about the birth of soundies in 1927. References to The Jazz Singer, cameras in sound-proof booths, desperate measures to hide microphones, the invention of ADR and it's rumored to be based on a true story, this is a fascinating film for film lovers. On that level. On another level, it is just plain silly and fun. Highly recommended (multiple times).
Ed Wood (1994)
Wonderfully entertaining, whether you are into movie making or not.
Boogie Nights (1997)
Another mainstream and very entertaining picture. It's about making porn, so it's got a lot of adult language and situations, but it's not pornographic in and of itself.
Oh, there are just too many to list, so let me end this with two more recommendations and a warning: RKO 281 (1999) and Sullivan's Travels (1941) are both rather good, but Tristram Shandy (2005) is not.
Meta TV? There have also been countless Meta TV shows (like Greg the Bunny and (My Name is Earl, Season 4, ep1).