I'd tell them to watch from the beginning, because that's the most rewarding way of doing it, in my opinion. If they found season 1 too hard to get into I'd tell them to watch a select few episodes such as
Captive Pursuit, Vortex, Duet and
ITHOTP, then the Circle trilogy. If they still weren't into the show at that point I'd go the nuclear route;
The Jem'Hadar, The Search, Improbable Cause/The Die is Cast, The Way of the Warrior and
The Visitor. If that doesn't pique their interest then it's a lost cause.
I completely agree, and this is what I'd do - and have done in the past. DS9 just isn't a show where you could show them
any episode to start with, even if it was as fantastic as The Visitor or In the Pale Moonlight. Without understanding who all the characters are, it just doesn't have the same impact.
I've tried showing friends random episodes of DS9, as well as TNG and Voyager, but that method just can't convey
why the series is so great. Even though its my favourite series, its also the hardest to get other people into for that very reason.
I'd show them what I think exemplifies DS9 and that, to me, is exploration of morality. If I had just one chance to hook a new comer I'd probably show them
In the Pale Moonlight even though the roles of the characters and their behavior wouldn't be as "shocking" if you didn't know Sisko or Garak or the war or any of that. I think the dialogue in the episode would be enough to convey what made the show worth watching (for me anyway.) If that was too complicated for them I'd refer them to the Star Wars prequels and politely ask them to exit my home and never return.
-Withers-
Personally, I don't agree with this method at all. You summed it up yourself when you said, "the roles of the characters and their behavior wouldn't be as "shocking" if you didn't know Sisko or Garak or the war or any of that". And because of that, you can hardly fault them for thinking the episode is 'too complicated'! If it was the first episode
I saw, I'd be confused!
Without knowing who all the characters are, as well as the backstory, it just doesn't have the same impact! And remember, newcomers won't even be able to identify who all the characters are!
That's also why I don't agree with introducing them in say, Season 3 or 4 - sure, the show started picking up there, but you're still missing out on information. You'd need to explain who the main characters are, who all the recurring characters are, what the premise is, you'd need to explain Bajor, Cardassia, the Wormhole/Prophets, and the Gamma Quadrant, and of course, the Dominion, and that's not even going into past episodes to explain the actions or references, etc.
IF they really weren't getting into it, then I guess I would try to show them select episodes of season 1 - 2, but I still think thats better than jumping straight in.