The crew of the Enterprise is desperately in need of a break, and the uninhabited planet they've just found seems like just the thing -- until members of the landing party begin seeing all manner of impossible things. From fictional characters to classic airplanes to wild animals, antique firearms and medieval clothing, and even Kirk's Starfleet Academy foe and flame. It seems whatever someone imagines on this planet somehow becomes real... and deadly.
This is Star Trek's first real comedic episode because no one seems to be taking it seriously at any point. McCoy sees life on a supposedly uninhabited planet, but doesn't seem appropriately alarmed. Sulu finds a gun that should not possibly be there, and his first instinct is to just pick it up and start firing it for fun. Kirk encounters a former school bully, and is more interested in fighting him that asking what the hell he's doing there.
They're all so slow on the uptake that even after all that, when Yeoman Barrows shows up with her uniform half torn off by an assailant, Kirk asks if she might be imagining things. Of course, if anyone was reacting to any of this in a realistic way, it would be a horror show, not a light romp. And so we get wild decision making like finding a dress in the middle of nowhere and deciding to put it on. We get McCoy dismissing something as a hallucination even when he knows the person he's with can also see it.
It's a shame that script is so rough and disjointed, because the production values are sky high for the time. There's extensive filming on location -- at Africa USA and Vasquez Rocks. (Though Star Trek's most famous trip to the latter spot would come later in the season.) An actual lion is brought to the filming. (Also, reportedly, an elephant that wasn't filmed when the shooting day ran long.) And no, the White Rabbit costume that kicks everything off doesn't seem especially expensive-looking... but that may be because all the money had been spent on an armored, mounted knight.
Some aspects of the episode play well. Spock essentially tricking Kirk into going on shore leave is a fun exchange between the two. Kirk's pining for a lost love is an intriguing thing to learn about the character. The fistfight between Kirk and Finnegan is full of some pretty great stunt work (even if you can clearly see that stunt performers have replaced the actors). And if you'd been watching this at the time, in 1966? With all the characters coming and going from one episode to the next, you might have actually believed that Doctor McCoy gets killed halfway through the episode!
Other aspects of the episode haven't aged well. The soundscape of the alien planet is a constant background drone that sounds distractingly like a transporter. Composer Gerald Fried's Irish jig for the character of Finnegan is a cringe-worthy cliche. (Though not the worst thing Star Trek ever did to Irish people.) Yeoman Barrows' strange interactions with Doctor McCoy reflect a decades-old thinking that a woman can go from being assaulted to feeling flirty in the span of a few minutes.
Other observations:
- When Yeoman Barrows tries to massage the kink out of Kirk's back, he mistakes her for Spock. She must have some serious finger strength.
- In the natural outdoor lighting of this episode, you can sometimes see the true green-like color of the famously "gold" uniforms.
- We seem to be back to "pre-shuttlecraft" thinking. In another crisis where a shuttle would be really handy, they apparently don't exist.
- Not only does the airplane footage clearly come from a different source, but it's not even the same kind of airplane in different shots.
- There is one unbroken camera take where you see the tiger in the same space as the actual actors. And you can also see the chain on the tiger's neck that of course is there.
- When Barrows changes out of the princess dress back into her ripped uniform, it's now ripped on the opposite side.
- Spock behaves in a weirdly suave manner with with McCoy's go-go dancers.
- This is one of many classic Star Trek episodes that ends with everyone on the bridge having a hearty laugh. Though it's not clear exactly what "joke" has been told to spark the laughter.
At some point, if you can make peace with the fact that no one in this episode is going to behave rationally, you can extract some small pleasures from it. Still, I'd say "Shore Leave" is a C+ at best.

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