Director: Billy Wilder
One of the most bizaare and cynical films ever to come out of Hollywood, Sunset Boulevard remains one of the best movies about the business of making movies. A struggling writer stumbles upon the decrepit mansion of a faded star. From there unfolds a stinging satire of delusion, ambition, and broken dreams. Double Indemnity was hot, and I haven't seen The Apartment, but I'm not sure if Billy Wilder ever did a better film than this. Gloria Swanson delivered one of the most memorable performances of all-time as Norma Desmond, the quintessential has-been. The film got nominated for 11 Oscars, but maybe because it hit too close to home, it won only three, one for its dark and carefully observed screenplay.