Original Airdate: 12/29/1966
Synopsis (from the official website):

A U.S.S. Enterprise landing party beams down to an uncharted planet. The planet seems like a perfect candidate for shore leave with its "Earth-type" characteristics. Kirk sends McCoy down with the party to check it out.

McCoy's first encounter on the new world is with a life-sized white rabbit in a waistcoat, being chased by a little girl in a pinafore. Kirk answers McCoy's somewhat odd call for help and beams down himself to find his old rival from his academy days, Finnegan. While trying to catch his old enemy, Kirk meets Ruth, an old girlfriend. He notices that neither Finnegan nor Ruth have changed in appearance since he's last seen them. Elsewhere, Sulu attacked by a Samurai Warrior while others are chased by tigers and aircraft.

McCoy, who has paired off with Yeoman Tonia Barrows, is killed by a black knight on horseback. As the perils become more and more deadly, Kirk and Spock realize that their thoughts are somehow coming to life around them.

An old man appears, explaining that this planet is designed as an "amusement park," and he is the Caretaker for the world. The planet is not meant to be hostile, and the results of one's fantasies are not lasting. McCoy appears, healed, with a Rigel Cabaret girl on each arm. Tonia disengages the good doctor and they go off to spend what promises to be an enjoyable vacation together. The Caretaker invites Kirk and his crew to spend their leave on his planet. Kirk agrees, realizing that once warned, it would provide a most diverting vacation spot. As he makes his decision, Ruth appears.

I am not entirely sure where to start. Shore Leave is on a very short list of my least favorite The Original Series episodes. It's hard to compete with Spock's Brain, but I think I might dislike Shore Leave even more. The concept of the episode is perfectly reasonable, and in 1966 might have been the first of its kind in science fiction. The "thoughts come to life" concept has been used and reused in science fiction over the years, and the concept itself almost salvages the episode. Unfortunately, the painful dialog, embarrassing effects, terrible costumes, and the shameful acting by some of the guest stars just makes the episode too hard to watch.

Take the character of Finnegan, for instance. It makes sense to bring an old nemesis of Kirk from his largely unknown academy days to provide the "villain" for the episode. But did they have to make the character so comically annoying that the impact of his being a bully to the great James T. Kirk was lost? Perhaps the actor simply was miscast or tragically overacted. Perhaps the direction was poor, or the script didn't offer much. Regardless, the character wasn't simply a buffoon, he was a caricature that had me seriously considering pressing fast forward every time he was on screen.

Another issue I had with the episode was the ham-handed, poorly concieved, entirely inappropriate "relationship" between the McCoy, the ships chief medical officer, and an enlisted crew member-something that probably would have been against regulations even in the non-militaristic Starfleet. The way the the romance was portrayed also strayed (as was typical in the first two seasons of TOS) far too close to the worst of the stereotypical way that women and relationships were portrayed on television in the 1960's.

While the end of the episode manages to make sense of the confusing and poorly conceived story, the resolution is so brief that it does nothing to explain what could have been fascinating-what is the story behind the Caretaker? Who built these planets? What powers them? An episode that was 10 minutes of the "if wishes were horses" theme and 33 minutes minutes pursuing these questions would have been far more meaningful and interesting than the bargain store costume bunny rabbits, enraged samurai, and yet another "death scare" for one of the series regulars.