1. The Motion Picture: Yes, it's seriously flawed. But it's the closest a Trek film got to exploring space, not just blowing stuff up. I love the themes of the purpose of imperfection, the limits of logic and knowledge, and the desire for easy answers in the divine. It seemed fitting that in the first Trek film, the crew would get a glimpse of humanities destiny.
2. The Wrath of Khan: Great drama. Kirk loses his best friend, gains a son, and learns to enjoy every minute of life, no matter how many have come before, or how many are left. And the Mutara Nebula battle is still my favorite from the Trek films. The scenes on and outside of the ships are equally tense and exciting.
3. The Undiscovered Country: Nice send off for the original crew. Humanities maturation never ends. We may grow beyond our internal conflicts, but we still have to grow with the rest of the universe. No matter what you have achieved, you still have a long road ahead toward true perfection, and enlightenment. So the adventure may never end.
4. The Search for Spock: If it wasn't so sad, this would be an adventurous romp. After saving the universe for 20 years, the crew says f-you to Starfleet after being told to not save their friend. But miracles come with a price.
5. The Voyage Home: A nice, fun change of pace after the death of Spock, death of Kirk's son, destruction of the Enterprise, and the crew becoming outlaws. They can keep the Greenpeace message, but leave the culture clash humor.
6. Nemesis: The Next Gen crew finally faces an interesting, and scary villian in a film. An angry young man, stuck between worlds, trying to become someone on his own, instead of having an identity forced apon him by others. Data is no longer the naive robot-child grasping for some understanding of humanity. He's a confident friend helping with advice, and ultimately sacrifice. The rest of the crews role in the film range from adequate (Picard), padding (The Rikers), or irrelevent (everyone else.) And the overall story makes a decent February sweeps two-parter, but not the finale of a film franchise.
7. First Contact: If you take this movie apart, some of the bits and pieces are enjoyable by themselves. But as a whole, this is a mess. It's designed backward. It's most tense at the beginning, and quickly loses steam, dragging to an underwhelming halt. The film starts with word of an unstoppable force heading toward the Federation. That force turns out to be one Borg cube. Yep, that's never been defeated before. How long does it take the Enterprise to destroy that cube, 20 seconds. The cube launches a smaller craft that rewrites history in favor of the Borg. How long does this alternate history exist, 20 seconds. And what does the majority of this film turn into, "Starship Mine." The first shipbound confrontation with the Borg is frightening, disorienting, and claustrophobic. But they become increasing slugging, leading up to the slow-motion button pushing session on the soundstage...oops, I mean deflector dish. And the logic is just perfect in these characters. Zefram Cochrane is building a warp ship to make money in a world that has been crippled by a third World War. Yes, the idea of a hero not being what we thought he was can be entertaining, but it makes no sense in this context. And since when do the Borg need a counterpart to bridge some gap across the civilizations. What happened to "your culture will adapt to service us," not we want to understand you better so you'll like us a little bit more. Just impose your imagined superiority on humanity, take what you find useful, and discard the rest. Nice Barclay cameo, though.
8. The Final Frontier: To be fair, this movie should be last on my list. The only way I can give a few extra points, is by viewing most of the film as a dream Captain Kirk is having, that showcases his ego, and his friendships. I love the line, "What does God need with a starship?" But nothing can be taken seriously in this movie. Spock has a magical half-brother out of nowhere. Everyone on the Enterprise and in a small colony are weak-minded sheep, except for Kirk. The Enterprise has 21, no 60, no 80 decks, and can travel to the center of the galaxy, which is an oil stain, like it's right next door.
9. Generations: I'm still waiting for the movie described in the trailer. Two generations didn't come together to save the universe as was promoted. A wimpy captain put together a half-assed plan to save a bunch of faceless aliens from a well spoken, but ultimately stock villian. Yes, the star destroying weapon adds a little danger to the story, but it begins and ends in a 15 minute span. Picard's acceptance of mortality is nicely handled, but Kirk's is better in "Khan." And the less said about the death of Kirk, and the destruction of the Enterprise-D the better.
10. Insurrection: Let me get this straight. It's better for 600 freeloading, self-righteous snobs to live forever in a stagnant , pre-industrial state than for billions of evolving space explorers to receive the best medical care the universe offers? Are you serious? I understand the basic message of not sacrificing your core beliefs in the face of great danger. Can this rule be applied to every scenario, especially this one? NO! Plus, it would have been nice to see the Enterprise crew versus the Federation. But that's not what happened! We got the Enterprise crew versus a bunch of thugs who had a Starfleet Admiral provide a little support. Boob jokes, pimples, head injuries, hormones, annoying brats, singing, dancing, is this a "Star Trek" movies, or one of those pop-culture parody films that won't go away.