Note: the number in brackets is my ranking.
The Original Series
Star Trek: The Motion Picture, Robert Wise, 1979 [7]
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Star Trek II: The Wrath of Khan, Nicholas Meyer, 1982 [1]
The second instalment of the movie franchise sees the return of a villain from the TV show's first season, the super-human Khan, who's hell bent on revenge. Kirk and crew have to stop him from using the Genesis Device, a life-creating machine invented by the ex-Mrs. Kirk and her son, as a weapon of mass destruction. Not only is the plot more focused than in TMP, but Kirk finally has to face up to the consequences of some of the total ass-pull moves he made earlier in his career, consequences that have deadly results for his closest friend. Said death is the most poignant and tear-jerking in all of Star Trek.
Star Trek III: The Search for Spock, Leonard Nimoy, 1984 [9]
My attempts to avoid spoilers in the previous synopsis have clearly failed. Spock is still out there somewhere, so Kirk et al steal the Enterprise to go find him. Although it does bring Spock back in a satisfactory manner, the film suffers from a lower budget and Nimoy's first-time direction.
Star Trek IV: The Voyage Home, Leonard Nimoy, 1986 [5]
On their way back to face court-martial for stealing (and subsequently blowing up) the Enterprise, Kirk and crew find the Earth being threatened by some space whales, so naturally they have to travel back in time to present-day Earth to rescue a pair of humpbacks. Yep. While not quite as charming as, say, "The Trouble with Tribbles", TVH manages to capture the campy fun of the 60s series.
Star Trek V: The Final Frontier, William Shatner, 1989 [12]
Spock's illogical half-brother steals the Enterprise to go look for God. Apart from some nice character moments (and so much Ho Yay!), this is pretty awful. Whose idea was it to let Shatner direct?
Star Trek VI: The Undiscovered Country, Nicholas Meyer, 1991 [2]
On the eve of the Klingon's entry into the Federation, Kirk and McCoy are accused of assassinating their High Chancellor, and the crew must prove them innocent. Better direction, better effects (featuring impressive morphs from a shape-shifting Iman), and a solid story, TUC is easily one of the best in the Star Trek film franchise.
The Next Generation
Star Trek: Generations, David Carson, 1994 [11]
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Star Trek: First Contact, Jonathan Frakes, 1996 [4]
The Enterprise-E (yes, they blew it up again) travels back in time to thwart the Borg Collective's plan to stop humans from achieving warp speed. Lots of action, good effects, a bit of humour, and plenty of suspense. It's a really clever way to let us see the most important moment in Star Trek's backstory.
Star Trek: Insurrection, Jonathan Frakes, 1998 [6]
Picard and crew go rogue to stop a Federation plot to meddle in the affairs of a peaceful planet. An intersting concept that plays out fairly well, though the silly campy moments aren't handled as well as in TVH.
Star Trek: Nemesis, Stuart Baird, 2002 [8]
The Romulan clone of Captain Picard seeks revenge on his creators, the Federation, and the Captain himself. Again, an interesting concept that's entertaining, but I didn't like it because they killed off my all-time favourite Star Trek character for real and didn't even give him a funeral.
The Reboot
Star Trek, J. J. Abrams, 2009 [3]
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Star Trek: Into Darkness, J. J. Abrams, 2013 [10]
Kirk and the Enterprise crew must stop Benedict Khanberbatch from wrecking destruction across the galaxay. References to TOS seem a bit more forced this time around, plus it continues to draw out the 'how Kirk became Kirk' angle instead of just letting him be Captain Kirk. Really, it's just a shoddy remake of Wrath of Khan.