If I could choose, I'd end it at
First Contact, but as someone pointed out earlier, the success of FC would lead to more movies... so I'd have to vote for not ending at "All Good Things" (though there are days that I wonder).
A lot of the quibbles that I had with
Generations have disappeared over the years. It was a bold (though ultimately unsuccessful) attempt to tell a grand story about life and mortality, but it fell apart the moment Picard tries to enlist Kirk's help. However, I really can't fault it for trying and failing. (Bonus points: the
Enterprise-D bathed in yellow sunlight. Too bad she wasn't from planet Krypton.)
First Contact is, distilled to its most simplistic form, a zombie movie in space with plot holes and continuity issues, but it's also more than that. It serves as an origin story for Star Trek itself, somehow capturing the essence and idealism of Star Trek (TOS-style idealism, to boot). Sure, some of it is weird (yes, there's no money... only "Federation credits" in the future). Sure, the movie's setting is pretty dark. The world is horrible (WWIII aftermath). It turns out that space can also be horrible (the Borg). People are imperfect (Lily's takedown of Picard is awesome, BTW). Ultimately, though, the optimism shines through strongly. There's a better future waiting for everyone: we all can be taking the first steps into a new frontier if we really want it. Even if the future can be horrible at times, it's still one with worth working toward. Somehow,
First Contact simply works. (Bonus points: Lily Sloane.)
As inexplicably stuff comes together for
First Contact, allowing it to transcend its popcorn-flick-ness (?),
Insurrection doesn't work. It had a worthy premise, but it's execution is just plain bad, with the plot holes being bad to the point of defeating the premise. At least with
First Contact, we can hypothesize in-universe reasons/Treknobabble for Borg time-travel issues. Even visually,
Insurrection somehow manages to look bland. I appreciate what Piller was trying to convey, but executive meddling seems to have killed the film before shooting even started. (Bonus points: ... it still made money?)
Nemesis is savaged more for it "killing" the movie franchise than for the actual movie itself, which was mediocre but still more entertaining than Insurrection. Visually, it holds up the best along with
Generations. The cast seems weary throughout the film (likely due to real-life weariness with regard to the director). Shinzon's desire to destroy Earth seems out of the blue, but I suppose we can chalk it up to insanity. Unfortunately, Nero makes for a much better madman in a much better Trek movie just a few years down the line. As they say, a film's only as good as its villain. (Bonus points: ... thanks for ST09 and STID, sorta?)
As an aside, I think it was
Insurrection that killed the TNG movie franchise, not
Nemesis. With slowly
increasing box office returns (adjusted for inflation) for three straight movies (TUC, GEN, FC) after the disaster of
The Final Frontier,
Insurrection somehow managed to destroy any interest remaining in TNG. The four year gap between INS and NEM only served to reinforce that disinterest rather than build anticipation (which might have happened if they had a four-year gap after
First Contact instead, which in turn would have given them time to make a better follow-up film).