So, keeping that disclaimer in mind, here are my favorite five episodes:
#5) The Measure of a Man: This is my pick for a 'new-to-Trek' story. Lt. Data, an artificial life form serving as a Lt. Commander on the Starship Enterprise, receives an order to submit to disassembly by a Starfleet scientist named Maddox. While intrigued with the possibility of creating more androids like him, Data is not convinced the research will work, and might even render him inoperable. When he attempts to resign his commission, Maddox heads him off at the pass, filing suit with the newly created JAG department to argue Data is, in effect, property of Starfleet.
By focusing tightly on the relationship between Picard, Data, and Riker, the drama centers on the moral question of what sort of society Star Trek is. Even someone who didn't know what a replicator or Vulcan were would get a sense of the philosophy animating the Star Trek universe. What I really appreciate about this episode, twenty years later, is how each character must make their own adjustment to the question Data's personhood. Riker has to finally get his hands dirty, given the odious task of proving androids have no rights. Even Picard, who goes to great lengths to protect Data's rights starts the episode with a rather hazy notion of what exactly is at stake in the courtroom. It's an encounter with Guinan that finally helps him realizes what mass produced Datas without right really represent: a race of slaves.
4) Yesterday's Enterprise: The other really great example of a tiny bottle world created within a single show. The Enterprise D encounters a spatial anomaly, a ship emerges...and everything changes. The ship turns out to be the Enterprise C, lost in battle 18 years before, apparently while defending a Klingon base from Romulan attack. As Data observes, this is a pity as the present war with the Klingons might have been avoided had the grand gesture taken place.
This is an extremely skillful way of introducing an alternate timeline, where the Enterprise D wasn't built as a ship of peace and exploration but rather a warship in the midst of a vast and tragic war. This is a war Picard chillingly informs the captain of the Enterprise C has not going well for the Federation. The entire cast is terrific in this episode, Tasha Yar gets a more fitting end to her story (an ending they should have just left be instead of gumming it up with the Sela storyline) Goldberg sells Guinan's Cassandra plight over knowing that the time period is 'wrong' while not being able to describe why. As usual, Patrick Steward also shines, here slightly modulating this alternate history Picard into a sterner, less optimistic military leader. One enjoyable aspect of the show is how much milage they were able to get from a few simple changes to costume design and lighting. This isn't a show that would make a lot of sense to walking into Star Trek without any background, but grows in resonance the more of the series you watch. Unofficial sequels: Parallels and "All Good Things…"
3) Cause and Effect: The most successful Brannon Braga story, a nifty "Ground Hog's Day" concept that deftly allows each repetition of events to slowly build meaning with each rewatching. The Enterprise is caught in a repeating time loop, each loop ending in the destruction of the Enterprise. But what really sells this story is how the logic of each reiteration takes on different meanings with each pass through. Worf, Data, Riker and Crusher gather for four separate poker games, the deja vu striking each character differently, the scene played at first for comedy, then with eerie foreboding, and then dread. This is an ensemble episode, giving every crew member a chance to shine, something that the show isn't always able to pull off successfully. And, while technobabble does make its appearance, the problem and its solution are both executed in a refreshingly straightforward manner.
2) Ship in a Bottle: Finally revisiting a mostly successful second season episode ("It's Elementary, My Dear Data) that brought Dr. Moriarty into the 24th century, this episode gave us another truly great sixth season concept episode. Moriarty, who has been stewing in the digital storage of the Enterprise for four years is suddenly released by Reginald Barkley, a hapless systems engineer introduced in "Hollow Pursuits." When Moriarty explains to the Picard and Data that he has had awareness of the passing of time, the crew endeavors to help him, trying to figure out someway to allow him to escape the confines of the holodeck program and his own programming. But this is Moriarty, programmed to be Data's greatest adversary, and part of the fun of this episode is knowing that Picard and Data are walking into a trap without being able to see where the teeth meet. Without giving too much away, the episode does a masterful job of slowly layering complication upon complication until the final act has all of the ambiguous possibilities of a Christopher Nolan film. It also contains the best final line of any episodes, save this one:
Which takes us too...
1) The Inner Light: Any episode that can wrench so much feeling from a man playing a simple tune a tin flute, has secured its place in television history, let alone Star Trek history.
But this is one of my favorite episodes for the tiny world it manages to create within its 45 minute run time. One of the true delights of this episode lies with how Picard comes to transcend and believably inhabit this alien world, and a life that represents, in some ways, the antithesis of everything he has devoted his life to achieving. His Kataan life includes a wife, children, a sedentary existence and an insoluble problem. And yet this episode, more than any other Picard-centric episode, reveals the endless depths of the character Patrick Steward was able to create. The gravitas of Steward always made the captain of the ship the emotional center of the stories, but this was the episode that brought all of the pieces together, cementing Jean Luc Picard as one of the truly original and fully realized fictional characters.
And that doesn't really even begin to scratch the questions this episode casually raises during the course of its heartbreaking story, not just about the nature of reality, but the purpose of existence. For how could a life created for Picard, that he lived in full possibly be called false? How could his 'real' life aboard the Enterprise possibly be enough after all that he had seen and lost? I think this was the last episode of Star Trek that can be watched without wondering why the 'reset button' has to be pressed at the end of each adventure. It's telling that Picard would return again and again to that simple flute, using it as short-hand for a character who had gained a measure of self-knowledge at an appalling cost.
Each of these episodes helped secure Star Trek's place in the history of television and while most of them appear regularly in lists like these, I do feel obligated to mention the following runner's up in terms of best episodes: Best of Both Worlds (Part 1 & 2), Chain of Command (Part 2), All Good Things, I, Borg, Offspring, Family, Parallels, Lower Decks, and Q Who. These are all recognized classics and well-worth inclusion on any list.