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Star Trek: Enterprise is the last TV series, but I've watched it first because it shows initial story (2100s). I've just finished watching season 4 of Star Trek: Enterprise.
For 2200s, I've watched all Kirk movies, but not the original series of 70s.
As per Star Trek timeline, next comes Star Trek: The Next Generation. But, unfortunately, its not available to me at this time. Next one is Star Trek: Deep Space 9. Is it OK to watch Star Trek: Deep Space 9 after skipping Star Trek: The Next Generation?

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    Why would you possibly want to do that??!! – ThePopMachine Jan 14 '12 at 1:03
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    Sign up for a free Netflix account - it has all 7 seasons of TNG available. Watching TNG before DS9 will give you a much better overall sense of the continuity and universe. – Omegacron Feb 15 '14 at 18:01
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    @Omegacron: not in the UK it doesn’t. Here we only get season 4-7 of TNG, although that works fine because “The Best of Both Worlds, Part 2” really is designed as a standalone episode NERD RAGE. – Paul D. Waite Sep 1 '14 at 9:17
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    Speaking from personal experience (am currently watching DS9 without having watched TNG) I am finding it totally fine and am able to follow fine, although Q was left a little explanation-less at first. – shanodin Jan 27 '15 at 16:47
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    @OrganicMarble: You are very lucky if you still have the opportunity to watch TNG for the first time! – ThePopMachine Aug 29 '18 at 18:09
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Two things to consider:

  • Seasons 6 and 7 of The Next Generation overlap with the first two seasons of Deep Space Nine
  • The Next Generation was mostly an "Adventure of the Week" show, although with gradual character development. Deep Space Nine was very much on a mythic story arc, with a number of major arcs leading through - especially once you get past season 1.

Apart from a couple of crossovers (a two-parter TNG episode is set on DS9 - and the Picard/Borg link in the pilot) - and the appearance of races and characters from the earlier TNG into DS9, I don't think that you'd have any problems following the story and development in DS9.

This becomes quite obvious with races like the Ferengi (introduced as [comically inept] pirate raiders in TNG, becoming amoral traders and merchants in DS9), Cardassians, and Trill (these two were simply underdeveloped on the introduction, and DS9 forced the writers to consider more detailed histories and cultures for the two races) - who are very different in the first appearances in TNG when compared to their representation in DS9 and the latter seasons of TNG.

That said - there is one particular awesome late TNG episode that includes the Cardassians - the two-parter Chain of Command. For me, it helped cement the Cardassians as a race and completely supplements their development in DS9.

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TNG introduced some people and cultures that you'll see on DS9 so it would be helpful to watch the earliest episodes related to them.

  1. Q: "Encounter at Farpoint"
  2. Ferengi: "The Last Outpost"
  3. New-style Klingons: "Heart of Glory", "The Icarus Factor" (ascension ceremony)
  4. Cardassians, Chief O'Brien: "The Wounded", "Chain of Command"
  5. Bajorans, Maquis: "Ensign Ro", "Preemptive Strike"
  6. Trill/symbiont: "The Host"
  7. Evil Riker: "Second Chances"
  8. Vash: "Captain's Holiday"
  9. Lwaxana Troi: "Haven", "Manhunt"
  10. Borg: "Q Who?", "The Best of Both Worlds"

Without these episodes, some of the stories will seem odd to you because of the missing contexts. But DS9 quickly introduces its own unique situations and characters and you'll be able to enjoy it without having seen TNG.

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    Don't forget Q and Vash (sorry, I don't have all the episodes they were in). – Xantec Jan 13 '12 at 19:39
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    Arguable - the Ferengi and Trill in TNG are quite different to their representation in DS9. Cardassians also changed after "The Wounded" - the remaining TNG Cardassian episodes are after DS9 had already begun airing. As for the rest - there is some backstory to be gained from watching the odd TNG episode, but I doubt that anyone will be left scratching their heads after watching the DS9 episodes without the TNG ones. – HorusKol Jan 14 '12 at 0:02
  • I agree with @HorusKol - the Ferengi changed radically after The Last Outpost, and most of their episodes are in DS9 anyway. Their Enterprise appearance was somewhere between The Last Outpost and their real nature. – Izkata Jan 14 '12 at 0:46
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    Likewise with the Trill and Bajorans. The Trill seen in TNG were never seen again in DS9, so there's not much lost there. And so much happens with the Bajorans in DS9 that the small amounts learned in the handful of TNG episodes don't really matter. – Izkata Jan 14 '12 at 0:47
  • Thanks for the comments; I agree with them. I've added Q and Vash to the list. – Kyle Jones Mar 30 '13 at 7:05
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There are sporadic episodes which deal with the events or characters established in TNG. However, I do not feel that these episodes will leave someone in the dark and are not critical to the main storyline of DS9.

The pilot episode actually has Captain Picard as the one delivering Benjamin Sisko to DS9. Sisko is hostile towards Picard because of his involvement in the battle of Wolf 359. This was primarily to bridge the connection for viewers of TNG with the new DS9. Just like Voyager begins with them meeting on DS9 (to make the second bridge to the third installment).

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    @MikePeterson If you can find and watch the two part TNG episode The Best of Both Worlds prior to starting Deep Space Nine that will then give you the back story to the opening scenes of the first episode. – Xantec Jan 13 '12 at 18:14
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Skip DS9? Watch Voyager instead? Blasphemy! Ideally we would just watch TNG and then DS9 (for the record, I consider DS9 the best Star Trek, and possibly my personal favorite show ever made). But okay, since ideally isn't always practical...

I do agree that you would be missing a lot of context in not knowing about the O'Briens or Worf's background with the Klingon Empire. I disagree, though, that watching Encounter at Farpoint, etcetera, would be the best choices (first appearances may not be the best examples), I have made my own list for your consideration:

2x14 The Icarus Factor (Worf)
2x16 Q Who (Q and Borg)
3x17 Sins of the Father (Worf)
3x19 Captain's Holiday (Ferengi, Vash)
3x24 Menage a Troi (Ferengi, Lwaxana)
3x26, 4x01 The Best of Both Worlds (Borg and Picard)
4x07 Reunion (Worf)
4x12 The Wounded (Miles, Cardassians)
4x26, 5x01 Redemption (Worf)
5x03 Ensign Ro (Bajor)
6x10-11 Chain of Command (Cardassians)
DS9 Season 1
6x16-17 Birthright (Worf; some takes place on DS9)
6x24 Second Chances (T. Riker)
DS9 Season 2
7x21 Firstborn (Worf and Alexander)
7x24 Preemptive Strike (Maquis)
DS9 Seasons 3-7

The first one might be scrapped if you know about Klingons already, but the others seem pretty important in what they introduce. Also, Season 5 has some REALLY good episodes (as do 6 and 7) but not too many are needed for understanding DS9.

Hopefully the ones I've listed will cover the Romulans well enough, though I am thinking of adding a few more. I am considering re-adding "Manhunt" from S2.

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DS9 storylines pretty much stand independent of TNG, so you could watch most of DS9 without previously watching TNG and not get lost on what is going on. But, a lot of DS9 is character-driven, and many character stories build on "backstory" established by TNG episodes. That backstory is needed to to fully appreciate what the characters are dealing with and get the most out of the show.

Overall, I think the best experience is to watch all of the series/movies in the order in which canon was built up (production/release/broadcast order). Although you can watch some episodes or movies as stand-alone experiences (many were written that way), you will almost certainly get more out of them when viewed in the context of previously established canon. Of course, much of DS9, like Enterprise's 3rd season is a serialized arc, so you need to watch it in broadcast order for the bigger story to develop properly.

I'd recommend holding off on DS9 until you have a chance to watch TNG.

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No, No, No, No, No....

Aside from the Sisko/Picard relationship which others have mentioned, you have none of the character development of some of the main characters in DS9.

O'brien, his wife Keiko, Worf, etc. You also know nothing of how the relationship developed between the Cardassians and the Federation.

You can't fully understand TNG episodes by picking out 7 or 8 episodes and watching them in a vacuum. You won't understand how any of those characters interact or relate to each other. So trying that to get caught up won't work.

And finally why would you want to do that? You're skipping maybe the best show ever made on television, and for sure the best science fiction show ever made(with maybe the exception of the original series or Voyager). It's almost blaspheme. You'll love Data, the funny scenes with Worf, the Borg, Q...there's so much it just doesn't make sense.

My recommendation is watch TOS, then TNG, then VOY, in that order. Skip DS9 and Enterprise and watch them later if you feel like it.

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