Sunset Boulevard (1950)
Billy Wilder co-wrote and directed this masterpiece about an aging, has-been silent screen movie star who, in her psychotic self-indulgence, believes that she can make a "return" to the big screen with the help of an unsuccessful writer (William Holden). Holden is fabulous as the cynical, downtrodden nobody whose motivation never exceeds cash or desperation, and former silent screen star Gloria Swanson is fabulous as Norma Desmond, also driven by desperation. "Sunset Boulevard" received numerous Oscar and Golden Globe nominations, including best actor/actress, writing, direction, cinematography, editing, and others, and should've won for all of them. You'll recognize some famous quotes from this film, including Desmond's explanation for her demise ("I am big. It's the pictures that got small."). Eric Von Stroheim plays Max, the mysterious butler who nicely complements the eerie tone of this brilliant cinematic masterpiece.
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