Those are great points. I’d be putting everything in chronological (production) order, just for clarification. I hope my friend will be willing to watch eight episodes because I really think it’s important to get a full picture of the characters and their history for the movies to have a great importance to the viewer.

For sticking to a solid five episodes, I think your choices are great. And even then, long-time fans such as us most likely weren’t introduced to the series with nearly this much attention to detail, so as long as a few good shows are picked, new viewers should be in good hands. Even something like “The Changeling” wouldn’t be a bad choice, though not as action packed as other episodes. Or heck, comedic shows like “I, Mudd” and “Shore Leave” would be good for people with a taste for corny fun. I think the best episodes would sometimes depend on the person being introduced.

Oh, I also forgot to mention that I really wanted to put “Where No Man Has Gone Before” on the list, as in my mind it’s one of the episodes that best personifies the series as a whole (which it was supposed to do, being a pilot after all). The only problem is that the full cast wasn’t in place, and so you don’t get the complete character dynamic. It’s just too different to be a good intro for new viewers.