Star Trek (1967), Season 1, Episode 28, The City on the Edge of Forever

Captain Kirk saves the Universe, with his love life in ruins... Captain Kirk does an Outlander as he goes back in time, meets a lovely Englishwoman and then he hopes to prevent the Nazis winning World War II.

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Star Trek VI: The Undiscovered Country (1991)

My God Jim...What a Way to Finish! Just before they retire, Kirk and McCoy try to make peace with the Klingons, after the Klingon chancellor is assassinated Kirk and McCoy are arrested....