The three best Star Trek films are:
The Wrath of Khan - A "nuclear arms" submarine thriller. (Khan and Kirk never meet in person.)
The Undiscovered Country - A murder/conspiracy mystery, prison break film and cold war allegory. It also explores Kirk's (and other crew members) racism towards the Klingons. (And vice versa. Some of the blatantly racist lines were re-written, struck or moved to other characters after Nichelle Nichols and other black actors (like the one Admiral) refused to say them or be present because they
were racist lines replacing distinguished black fellow with Klingons.)
Galaxy Quest - A big screen version of the TV show.
The Search for Spock and
The Voyage Home are companion pieces for the themes of Khan, aging and dying. Even The Slow-Motion Picture touches on it during the gang back together, Kirk dying to take over command while pretending he's not, Sulu talking about his own command, etc. Hell, even The Final Frontier taps into the narrative arc of the crew, especially the three main characters, developing as characters/relationships.
First Contact is considered an action movie but there's actually very little extended action in it, it's more the race against time on the planet, and then the interplay between an Alien-type trapped on submarine film vs. Picard's Moby Dick obsession and Data's quest for humanity being exploited/a gambit.
Insurrection's original idea (as outlined in that unpublished book
Fade In you can find or I can link) was supposed to be a rejection of the "darker" Star Trek that First Contact and the Dominion War represented, with Picard rebelling against The Federation betraying its ideals. It's still sorta there in the film, but it's all wack and shit with the 300 year old chick and the Son'a and so on.
Nemesis is the most actiony Trek film and it still has the best ship battles of the films, and the worst live-action scenes (dune buggy, shuttle in the ship, fight over the endless pit) of the films.
Generations is just a bad movie because it was written by the same two people at the same time as All Good Things and I think they accidentally put all their bad ideas in one pile and good ones in another. Also,
Generations had all sorts of studio mandates including involving Kirk, how much screen time each actor was to have, etc. which tears the plot completely apart because it has to fit those things in, in ways that don't make any sense.
If you look at the themes of
The Motion Picture and
The Final Frontier and ignore their execution woes (due in part to no budget constrants/2001's recent release and then extreme budget constrants with loss of special effects staff) they're very Trekian. Gods, creators, sentient machines, non-explainable alien powers, etc.
Master and Commander should have been like 20 movies. What a great movie.
It was supposed to be launching a series, but it was effectively a bomb. It's based off a series of like 20 books:
https://en.wikipedia.org/wiki/Aubrey%E2%80%93Maturin_seriesMaster and Commander is a god-like film. Not seeing the enemy throughout. And then the engagement is a quick and orderly battle in comparison to the rest of the film rather than an extremely long massive setpiece with overly grand strategy. (Their key ruse is...putting up a fake flag, then pulling it down two minutes later "SURPRISE WE'RE A REAL SHIP" and firing their cannons.)
That said, it needs a rifftrax. Kevin Murphy's pointed out there's not a single woman in the film but that's like the only thing they can make fun of. I strongly disagree, Russell Crowe has some incredibly strange reactions to things. (EDIT: There's also a fair amount of amusing "ooo me accent's slippin" moments.)
Regarding a sequel:
https://twitter.com/russellcrowe/status/198188938287001601https://twitter.com/russellcrowe/status/11710830559109120