This could be any movie, from the original cast up through the most recent movie. It's a difficult choice for me. But I would say Undiscovered Country. I am never bored of watching that one, despite seeing it many times.
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I so agree about Christopher Plummer! He was made for the role.
You've summed up my feelings about the two new Trek movies: "Nice." Visually amazing, but lacks something. New McCoy is trying way too hard to be the old McCoy.
What worked well with Plummer vs. Shatner is both of them are hams of the highest order and each of them were viying to be top sow in the movie. Of course we all knew who would win THAT one in the end.
That battle scene at the end of the movie is one of my all-time favorites.
I agree that First Contact was the best of the TNG movies.
But in this case, the first movie was a reboot of a TV show that for many fans was epitomized by action, intrigue and clever writing. The original movie was (forgive me, here) BORRRRRING! Star Trek II had to save the movie franchise. And it did!