28. Sunset Boulevard (1950)
Remember a time when Hollywood was an idealistic place where dreams came true and magic was made. Well, ironically, that was a Hollywood that only existed in the movies, at least until this brilliant Billy Wilder classic. In Wilder's Hollywood, people are cynical, abuse a studio-run system and take advantage of any connection they can to get ahead. The film is told from the perspective of down-on-his-luck writer Joe Gillis, after he has been shot and killed (one of the most interesting stylistic choices in film history). The late Mr. Gillis (played by William Holden), tells of how he ended up where he has ended up. Before his murder, Joe is experiencing a stall in his writing career and, through a series of events, finds himself at the Hollywood mansion of former silent screen star Norma Desmond (Gloria Swanson in an iconic performance). Norma soon takes him up as a co-writer for her screen comeback and takes him up as her lover, or gigolo. As the movie progresses, the characters spiral even further into their own cynicism, paranoia and indulgences. With an amazing Oscar-winning screenplay by Wilder and Charles Brackett, there are so many moments and lines that have become a part of our cultural lexicon (like "I'm ready for my close-up now."). Characters like Norma and her mysterious butler Max (played by former film director Erich von Stroheim) have been parodied left and right. The film is a masterpiece that displays the classic Hollywood style and speaks to an idyllic world smashed by the cynicism of time and power.
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