The City on the Edge of Forever (1967)
Not just one of the most beloved episodes of time-travel Trek around, but one of the most beloved episodes of Star Trek, full stop. Harlan Ellison’s tragic tale of James Kirk’s doomed love in ‘30s New York pushed the boundaries of the kind of sci-fi tale the original series could tell, and holds up today as a shining example of how Star Trek could use time travel in fascinating ways.
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