5. Sunset Blvd. (1950, Billy Wilder)
Few movies about movies are as ingeniously constructed and metaphorically flexible as Sunset Boulevard. Norma Desmond’s gothic mansion is a house of psychological horror for studio system cast-offs: creatives (William Holden), talent (Gloria Swanson) and even the help (Erich Von Stroheim). In one of its best tricks, it’s also a funhouse hall of mirrors. “Those wonderful people out there in the dark” (that’d be us, folks) may be friendly phantoms but they’re haunting Norma as surely as she’s haunting them. This faded Hollywood queen remains the cinema’s best and most ghoulish reminder of celebrity’s dark shadows, it’s hermetic mythologies and erosion into self parody, and the transience of the flickering image itself. What would Norma make of those wonderful people watching movies on their phones? “The pictures got small.” – Nathaniel Rogers
4. Man with a Movie Camera (1929, Dziga Vertov)
Man with A Movie Camera is the greatest of all films about film-making, because more thoroughly and complexly than others in this genre it makes the thematic investigation into the properties and processes of film-making the organizing principle of its form. There is a constructive synthesis of form and content in Man with a Movie Camera, that makes cinema into an emblem of the creative forces of life itself. So one must say that this unique film about film takes the project of being ‘about’ film further than any other film, and more seriously than any other film.
Another way to say this simply, is that all film about film is necessarily by definition reflexive, and self-conscious, but this condition is elevated by Vertov into virtually ametaphysical principle. It pushes self reflection to the point of absolute universality. Many of the great films on this list do this (fellini, Kiarostomi, Powell, Lynch) but Vertov does it in every moment and detail of his film. The completeness of expression in Man with a Movie Camera is unsurpassed.” – Larry Gross
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3. 8 1/2 (1963, Federico Fellini)
8 1/2 isn’t so much a film about filmmaking as it is a film about dreaming, daydreaming, and dream-remembering filmmaking . . . or life as filmmaking . . . or the frustration of translating life into filmmaking. Which is why 8 1/2 so gloriously succeeds in championing film as the ultimate dream-medium, since dreams make even failure into art. – Michael Joshua Rowin
2 . Close-Up (1990, Abbas Kiarostami)
Abbas Kiarostami’s Close-Up is not only an immensely poignant testament to the power of filmmaking, it’s also the cinema’s definitive self-portrait. A film that obliterates the reductive binary between “documentary” and “narrative” movies, Close-Up hijacks the tale of a plain and penniless cinephile named Hossein Sabzian, who had convinced a family of strangers that he was his idol — renowned filmmaker Mohsen Makmahlbuf — and that he would like them to star in his next film. Kiarostami, seized by the incident, visits Sabzian in prison and makes a film of his story, weaving footage of Sabzian’s trial together with dramatic reenactments of his fraud. What follows is a wistfully enigmatic saga about our collective need for narrative, and how the cinema’s fundamental inability to reproduce reality is ultimately what frees it to be of such profound importance to all of our real lives. – David Ehrlich
1. Contempt (1963, Jean-Luc Godard)
A film about filmmaking that is also about aging, love, and the changing of the guard at a very specific moment in history. Fritz Lang plays an old director making a movie adaptation of Homer’s Odyssey. Godard layers multiple epoch-defining shifts: from antiquity to now; within antiquity, from Greek to Roman; from the classical studio system to the balkanized world of mid-60s filmmaking. And there’s the central shift that reflects on all the others: the feelings between a romantic couple turning from love to contempt. The question that haunts the lovers and everything about the film: why did the past prove unsustainable? How does contempt for the ways things are now arise to turn them into the way things were? Lang’s presence embodies the Hollywood of the past; Contempt itself now feels like a relic of an older kind of filmmaking. But it’s worth taking a look at to try to get a feel for where movies are headed, when so much about right now feels unsustainable, when contempt is running high. – Tom McCormack
Honorable Mentions: F for Fake (1973, Orson Welles), Irma Vep (1995, Olivier Assayas), Day for Night (1973, Francois Truffaut), The Last Movie (1971, Dennis Hopper), Living in Oblivion (1995, Tom DiCillo), Millennium Actress (2001, Satoshi Kon), Sullivan’s Travels (1941, Preston Sturges), Duck Amuck (1953, Chuck Jones), Barton Fink (1992, Joel Coen), Los Angeles Plays Itself (2003, Thom Andersen), The State of Things (1982, Wim Wenders), Two Weeks in Another Town (1962, Vincente Minnelli), Singin’ in the Rain (1952, Stanley Donen and Gene Kelly)