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Montgomery Clift and Frank Sinatra were two Hollywood icons of the 50s and 60s, but their relationship was marked by ups and downs. Initially, Clift and Sinatra were close friends and hung out with the same group of actors and musicians. However, their friendship was put to the test when Clift was involved in a serious car accident in 1956, which left him with serious facial injuries. Sinatra was one of the few friends to remain by his side during his long rehabilitation, demonstrating deep loyalty.

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