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Introducing Someone to TOS: Which Episode to Show?

The Naked Time and Enemy Within are the best introductions to the characters so you are right about those two.
 
I think production order is VERY important - although not a serial, Trek is one of those shows where the characterization development shows right onscreen. This would be a good start:

Corbomite Maneuver - It really IS the 'third pilot' - it introduces he auidence to the more or less final cast, it makes the point over and over of the mission, and it includes one of the great Roddenberry 'surprise' endings. It really does set the tone of the series better than The Cage/WNMHGB..plus Steiner's score is one of the best ever.

Naked Time - as long as you point out it was made 20 years prior to Naked Now. Again, it has great character development - especially Spock and Kirk.

The Menagerie - both parts - she gets a little Trek history, and with NT, she gets the full development of Nimoy's Spock. If she sees this and NT, she will understand the Spock that Quinto reached for, and mainly succeeded in 'getting'.

THEN you can start scattering around, delving into the Coon/Lucas shows, and so on...
The Naked Time wipes the floor with Naked Now. In NT, you actually see some of the characters bearing their soul - Spock's emotional outburst is incredibly moving - and everyone gets to react in a different way and show a different 'true' personality. In NN, it's all about who'd like to get it on with whom.

I'm not sure if The Naked Time is the right choice for the first episode to see, though - you need to see the crew introduced as their normal selves for long enough before you get to see them show their suppressed personality. The episode is so much stronger when you already know these people. Same with all the great episodes in which people are acting uncharacteristically due to outside influences or we get to see a different universe (Amok Time, This Side of Paradise, Mirror Mirror...), they should all be seen only after you've already been introduced to the crew as they normally are.

Balance of Terror is a good place to start, or maybe The City on the Edge of Forever, or both - you get the best examples of both types of episodes represented, one on the ship with an antagonist and a tension among the crew, the other with characters away on a planet. But most other season 1 episodes could do, except for a few lame ones. Just don't start with a horrible episode like Mudd's Women!
 
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