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All of his films I think have a timeless look. The set-dressing, the costumes and the popculture references are mostly "timeless" (50's - 90's). The movies that age worst are often the special effect-laden and/or conventionally told ones. Since there are no fx's in his films (Kill Bill will probably look more Shaw Brothers than Matrix) and the characters and storytelling are the most unconventional around...
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"The Hughes wealth, power and sex appeal devastated scores of broken-hearted movie stars and made grown men shudder with envy and anxiety every time he entered a room. Mr. DiCaprio just makes any logical person over 14 wonder if he ever graduated high school." -Rex Reed
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