Ranking the Movies (Pre Reboot)

Wrath of Khan - Khan is great. Kirk is greater.
The Voyage Home - The whales are great, the comedy is greater.
The Undiscovered Country - Great cold war parallel.
First Contact - Borg, Cochran, great.
The Search for Spock - Not great, but bridges the story between ST2 and ST4, plus Christopher Lloyd.
Generations - Love seeing Kirk and Picard together.
The Motion Picture - Great concept, poor execution.
The Final Frontier - Poor concept, poor execution, but love seeing Kirk interact with "God".
Nemesis - What a mess.
Insurrection - Worse than a mess. Boring.

So I'm one of the few people out there who genuinely enjoyed Insurrection, so my list is going to be a bit different:

Wrath of Khan
Voyage Home -- "Computer? Helloooo Computer?"
First Contact
Insurrection
Search for Spock -- I would watch it just for Sarek
Generations
Undiscovered Country -- I would have ranked it higher, but I never could get into the Klingon prison scenes.
Final Frontier -- It was a crappy movie, but I love the Yosemite scenes
Motion Picture -- Zzzzzzzz.......
Nemesis

Wrath of Khan
The Search for Spock
First Contact
The Undiscovered Country
The Voyage Home
The Motion Picture
Generations
The Final Frontier
Nemesis
Insurrection

Yeah, that's about right.

The next generation movies were so disappointing.