Pretty hard choice to make, really, IMHO. First Contact was great and all, but to me it was the first example of the Borg getting just absolutely humiliated by an inferior race
The same ended up true for Voyager, where the Delta flyer was able to take on like 20 different ships and survived. As I remembered it, battles with Starfleet always went like this...
A cube comes, everyone is running scared s***less as they should be.
Everyone dies a terrible, terrible death, or they get assimilated (the part I always enjoyed so much). Whatever the case, it ends in a lot of demolished SF ships and then the Enterprise comes to save the day. It was awesome in Best of Both Worlds, but it happened again in First Contact. The Borg not ending the fight with a victory was negative enjoyable. I wanted the Borg to pull off a victory for once, and put Picard and any surviving non-assimilated crew in a position where he would have been stuck in the 21st century, and somehow bring together a group of survivors who would fight the Borg with guerrilla tactics or something like that. Most of them would be picked off by the Borg, and I would have watched and laughed as they died on screen! Fun for all!
Too bad movies don't change each time you watch them. The only thing that usually changes is you notice something that you didn't notice the last time you watched!
First Contact is still one of my favorites, despite the fact that the Borg failed...AGAIN. I mean, just send TWO cubes next time, or more! Mix it up, maybe even put some other fun stuff in there, like I dunno, the Borg diamond or sphere or dodecahedron or whatever other simple shape they can come up with (maybe a HYPERCUBE!!!), yes, a giant 4-dimensional-looking cube set forth to doom humanity! First Contact was still one of the best, though. Lots of action, didn't make me sad or anything. So thumbs up!
But all the movies are pretty good in my opinion. Even TMP and Final Frontier - those were still awesome despite the hate both those movies get. Did you see that massive eye candy scene in TMP? That alone was so epic, even by today's standards! Wrath of Khan was of course fantastic, the soundtrack in and of itself is a reason to watch it over and over again! Generations was actually pretty awesome, despite how much hate it sometimes gets. I remember a chill going down my spine the first time seeing not only the Enterprise get owned, but the planet getting blown away. Still don't get the fact that the Klingon Bird of Prey was able to do enough damage to the Enterprise to eventually destroy it, although it was in all fairness a larger class Bird and not one of those smaller ones, and it had a pretty good crew.
Star Trek 2009...it was a movie that I thought I wouldn't like - at all. I figured I'd be flipping the bird at the screen and then screaming expletives at the top of my lungs. But it astounded me in the fact that I loved it! So, my expectations were pretty low, but the results were so far above those expectations that it made ST11 my favorite! Funny how that works!
They still were able to continue the storyline into the future of the prime timeline, but somehow have it link to the past of another timeline. That was cool! At first I didn't like the design of the ship, but it grew on me and now I just love it! That ship is a real beast now! It's kind of a guilty pleasure for me to like all the new stuff, but I don't know, I just love it!