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 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...
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