In regards to what I consider to be the Gold Standard for a Anniversary Special I think Trials and Tribble-ations is the best of the Best. Not only is it a fun episode in its own right but it also really FEELS like a Celebration of Trek by revisiting one of series most iconic episodes and showing that while Trek could be serious it could also be silly and still hugely entertaining.
The Undiscovered Country is next up. Often regarded as one of the best films in the series TUC, as an Anniversary Special, is interesting as it also doubles as the Grand Finally for the TOS films and is also also seen as the Grand Finally that TOS never got in the show proper. It's also one of only two Anniversaries in the series that actually added to the lore of Trek by showing us HOW the Federation and Klingons became friends which is easily one of the most important moments in Trek History for obvious reasons. But more importantly then that is the journey of Kirk and his crew as we see their era come to a close and them making history with one of the best films in the series is certainly a Great High Note to go out on.
Then we have First Contact. What I like about First Contact is that, much like TUC, it's not just a celebration of the series but also adds to the lore of the series with the titular First Contract of the film. This film basically shows us the Birth of the Federation and I love everything that builds to that moment along with Zefram Cochrane character arc as he goes from drunk who just wants to get rich to seeing a brief climbs of the wonders the final frontier has to offer. One of my favorite moments is when he sees the Earth from Outer Space with James Cromwell fantastic performance as he is truly hit by what he has created. Picard's arc is also rather really good with him coming face to face with his most personal demons and him coming to realize that he is not as "Evolved" as he thinks. Another favorite moment of mine is when Picard has the Queen's skull-neck... thing... is how Picard kills it. I just LOVE Stewart's performance here as without any dialogue you can tell just what he's thinking/feeling. All the hate he has for the Borg and in the palm of his hand is the central mind of the whole thing. And what does he do with it, snaps it's neck to make sure it's Dead. Not only the best of the Next Generation films (though that's not saying much) but also one of the best Borg stories and a fasinating look into the creation of one of Trek's most important bits of Lore.
And now we get to Beyond which I think is a Criminally underrated film that deserved a LOT more love and attention then it gets. Chuck pretty much covered why I think that is so I won't repeat him but I will say is that it has what I think is one of the best space battles in the series with the destruction of the Enterprise (which I also consider to be the best "Death" of the iconic ship). This film also did a lot of things I wanted to see done in a Trek film. I wanted to see the crew stranded on a alien planet. I wanted more screen time between Spock and Bones, I wanted a character like Jaylah for SO Long in the series and she REALLY worked with the rest of the Ensemble and I would love to see more of her and I love how it really asks the question of just what the series is without straying to far into meta territory. Again, really underrated and at the very least I'm glad that the Kelvin Timeline got to go out on a high note.
The Voyage Home is actually my Very First Step into the Trek Universes. I remember coming in just as Spock was beamed onto the Bird of Prey while Kirk drove off with the woman of the week. Right from that moment I was hooked ad I wanted to know more about this film and what was going on. This was back when VHS was still being used so we couldn't just skip back to the start and see what was going on but the film as a whole was honestly so entertaining that I didn't much care as I was having so much fun. IMO, this is honestly a good intro for anyone new to Trek as you get the general idea of what the series is about, how it works, the characters and the fact that it uses Time Travel and ISN'T confusing to watch is a real testimony to this film's strengths.
Flash Back is, not terrible but after the other films and episode on this list it DOES stand out as the weakest of the lot. Even people who like Voyager and the creators of the series have admitted that it's just okay and isn't all that great when compared to Trials and Tribble-ations, never mind the other Anniversary Specials. For me, it's okay, it's nice to see Sulu again, it's got some solid action and an okay premise. But it is pretty forgettable as it doesn't have anything to help it truly stand out, either as a standalone story or as an story that's meant to be celebrating Trek.
Then again, when in the presents of some of the greatest stories in one of the most beloved series in pop culture I would consider it an honor just to be included in such a great list. So, how would you rank the Anniversaries of Star Trek?
