I'm always an unashamed sucker for this exercise.
Star Trek II- The Wrath of Khan
I recognize it’s unoriginal and cliché to choose this as the top movie. But, it deserves it. I’ve recently had the chance to watch it once or twice with friends who have never seen it before. This experience gives you the effect of “watching it for the first time through someone else’s eyes.” I can tell you that watching it from that vantage point has me convinced that not only is it the best Star Trek movie…but it is one of the franchise’s finest stories ever. The themes of aging, revenge, consequence, family and mortality were the perfect blend of elements for that time in the franchise. Add that to a colorful action / adventure plot with plenty of suspense and drama, and this is the crown jewel.
Star Trek- The Motion Picture
This may be the only true “epic” Star Trek ever produced. It’s odd that in many ways, it is the opposite thematically and from a pure presentation standpoint from TWOK, but yet it holds a spot as a “close second” with regard to my favorite movies in the franchise. The character stories of Kirk and Spock are very well done here (in fact, criminally underrated in my opinion) and interwoven very well with V’Ger’s story. The grandeur, visual appeal, soundtrack etc are all the best of the franchise. It also boasts a very pure sci-fi concept, which most of the franchise films did not.
Star Trek III- The Search for Spock
A very worthy follow-up to TWOK. There was probably no film or episode that did as much to build the world of Star Trek as much as TSFS did. It was a unique story (at the time) with the plot element of having Kirk and crew go rogue and steal the Enterprise. The themes of family and sacrifice ring throughout the picture. Shatner gives his best performance ever as Kirk. Kruge is a great villain and set the tone for 20 years worth of Klingon characters to follow. The destruction of the Enterprise is an iconic moment in cinema. Awesome movie.
Star Trek V- The Final Frontier
Most fans really dislike this film, but it has always been in my upper echelon. This (and TMP) are arguably the most traditional Star Trek stories in the entire film franchise. There are absolutely priceless and precious moments between Kirk, Spock, and McCoy here…and those relationships are one of the primary reasons I call myself a “fan.” The quest plot could have used a re-write or two to iron out some significant unevenness…but this is generally the kind of Star Trek movie I always wanted to see. Sybok is a very compelling character and avoids many standard moustache-twirling villain tropes. There are some genuine moments of awe and wonder in the film that I am always grateful for as well.
Star Trek: First Contact
Easily the best “Next Generation” movie, and certainly the one with the most enduring and “mass audience” appeal. Bringing the Borg to the big screen was a great (although obvious) choice, but interweaving it with a time travel epic about the birth of “Star Trek” as we know it was pretty brilliant. There’s some great performances mixed in throughout that reflect enough heart and drama to make this a really nice film. I think that, with no special effects, no sets, no action, etc…one of the best scenes in the film franchise is simply Picard and Lily confronting each other in the observation lounge. Awesome stuff.
Star Trek (2009)
This movie has its flaws and it’s eye rollers, but it is undeniably the film responsible for giving rebirth to my interest in Star Trek after a long drought of apathy. The opening 5 mins alone pack enough punch to carry the rest of the film. The fun, color and action/adventure of the original series makes a bold return in this film. While the plot itself is pretty pedestrian, it’s the characters, chemistry and performances that hit the mark. The action set pieces are a spectacle to behold as well. I find it easy to digest the ridiculousness of the Kelvinverse films by looking at them the same way I view Trek comics and fan films…very good “what if” type stories featuring characters I know and love.
Star Trek VI- The Undiscovered Country
I’m happy that to this day, this is viewed as a worthwhile send off for my original and most beloved heroes. It’s a fun movie with some nice character stuff and some cool action scenes, and it has heart and a few good plot twists to boot. That said, something about TUC has just never totally clicked for me. It feels far too rushed and too sloppy for me to take as seriously as some of the other entries.
Star Trek: Nemesis
I don’t hate this movie nearly as much as others do. In fact, if I’m doing a ranking of only TNG movies, this is a close second behind FC. Yes, some of the sequences are cringe-worthy (Kolaris III Mad Max scene, for example), but there is a lot of good stuff in here as well. The final action scene with the Enterprise battling the Scimitar is worth the price of admission, and a lot of the scenes between Picard and Shinzon are well written and well performed. I give Nemesis a ton of credit for at least TRYING to do something cinematic and epic. Even as it stumbled (and was shamelessly derivative)…at least it felt like a major motion picture and not a made-for-TV movie.
Star Trek Beyond
For a while, this was my favorite of the Kelvinverse films, but it doesn’t have the re-watch value I want in a Star Trek film. Lots of heartwarming character moments…far more fun character interplay than the other Kelvin films (and that interplay is far more aligned with the characters we came to know in TOS). It has a beautiful soundtrack and some outstanding visual appeal. But, Idris Elba is wasted as a cut-and-paste villain with questionable motives and when you start to break it down, this is a fun movie that doesn’t make a damn bit of sense, quite honestly. Still I enjoy the heck out of this if/when I turn my brain off and just go with it.
Star Trek IV- The Voyage Home
This is my least-favorite of the TOS films, but that doesn’t mean it’s awful by any stretch. I think it just misses the mark for me personally. I am more a fan of outer space adventure, and most of the “time travel to Earth’s past” stuff in the franchise just never excited me too much. TVH has a ton of heart and character-driven humor and a very Star Trek message built in. But, it’s one of the least-rewatchable of the entire franchise for me.
Star Trek Generations
This is probably the most “TNG-like” of the movies featuring that cast. It has gorgeous cinematography and a very underrated soundtrack. I love the opening scenes with the Enterprise-B and I think there are some great messages / thoughts mixed in about the nature of our mortality and life in general. The bottom line unfortunately is that this ends up being a convoluted mess and a missed opportunity with the Kirk-Picard crossover, and that’s hard to get past.
Star Trek Into Darkness
This is like an absolutely awesome theme park ride that makes you scream and shout while your heart thumps in your chest for the duration of the ride, but then you get off and you’re dizzy, nauseous, and then you vomit your hot dog and Mountain Dew all over the place, vowing that you’ll never get on again. It’s visually stunning, and is an amazing ride from start to finish…and the cast puts forward a wonderful and entertaining performance. But, the plot is so mind-blowingly stupid and inane that it gives me gas just thinking about it. From the moment Spock does his “Khan” yell to the end credits is virtually unwatchable for me (and I LOVE Star Trek)…I literally just don’t watch beyond the “death” of Kirk (which is a great scene).
Star Trek: Insurrection
The only Star Trek movie I actively dislike. As I’ve said several times, there is no greater sin when managing a franchise like Star Trek than to strive for mediocrity with your $60M sci-fi action/adventure major motion picture. INS has the distinction of being more forgettable and unremarkable than ¾ of the one-hour TNG episodes that were made for $1.5M a pop on syndicated TV. That’s inexcusable, and this is a bad film by any measure.