Charlie Chaplin once re-shot a scene in City Lights (1931) some 342  times before he felt he had gotten it right. 
In Some Like It Hot  (1959), Marilyn Monroe required 59 takes on a scene in which her  only line was "Where's the Bourbon?" 
 Similarly, Stanley Kubrick  required Shelley Duval to redo a scene 127 times in The Shining  (1980).
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