You might've noticed that Dragon Quest is about to celebrate its 25th anniversary in Japan with an anthology of the Famicom and Super Famicom versions of its earliest games. 25 years is a long time for any series, and anything that sticks around that long gathers baggage- in this case nine mainline games, and at least twice as many spinoffs in Japan. So the most important part of that baggage is the part that's most difficult to address: where do you start?
You'd think this would be an incredibly easy question to answer, with two obvious, simple answers- which are both, in my opinion, wrong.
1) At the beginning, of course! ...but then, the most modern remake of Dragon Quest/Dragon Warrior I is for the Game Boy. So unless you've got a Game Boy Advance or something older-school laying around and you want to trawl eBay for a copy of Dragon Warrior I + II, this is a solid barrier to entry. Even if you do, those games are pretty much at the technology level of the original Pokemon, and if you're not into retro gaming with all the clunky interfaces and dated graphics that entails, that may not appeal to you. (If clunky interfaces get your goat, then definitely don't start with the original NES Dragon Warrior.)
2) Dragon Quest games haven't had cross-game continuity since DQIII, so pick a game at your local retailer and get going! Which is slightly better advice, but there's still a lot of variation in the DQ games currently available. VI in particular, good as it is, I would absolutely not recommend to new players because of the grindiness of its job system.
My suggested play order is this: VIII (PS2) OR IX (or both!), then IV, V, and VI (all DS), then finally the Loto Trilogy of I-III once you're thoroughly hooked.
VIII is the most modern in its presentation, being fully voiced, an almost completely orchestrated soundtrack, and very bright, pretty cell-shaded graphics that defy the Realism Brownifier's dastardly attempts to suck color out of video games. It's also the easiest to pick up in terms of the combat systems. Just remember that in terms of presentation, you are looking at the best the series has done to date. It's all varying degrees of downhill from here. IX is the next step down graphically, an excellent game in its own right, and carries on the best streamlining aspects of VIII, and also has some more conveniences such as monsters that appear on the map so you can dodge them. However, its social and multiplayer aspects may leave you feeling like you're not getting the full game if nobody else you know plays Dragon Quest yet either. VIII is the best-looking and sounding, the easiest to play, and the most self-contained of the two.
From there, IV-VI ramp up the complexity while scaling back further on presentation, being as they are (slightly) modernized remakes of NES and Super NES games. You may find the difference jarring, but if you've liked what you've played so far there's a lot of good gameplay and enjoyable story to be had here. (And puns. So many puns.) IV has a large, likable cast and the best music of the entire series. V is a generational story where you play the hero as a child, a young man, and a father- and features the dawn of monster-catching in video games. VI goes back to a more traditional timeframe, but makes up for it with two world maps to explore. It's also absolutely the most complex of the DQ games currently or recently on the market, so no matter what order you choose I recommend leaving it for last. From there, I-III will be a slightly different experience, both because of the more-dated gameplay and graphics and because the translations are quite different from the modern Dragon Quest style... and in my opinion, not as good. (That is to say, not brilliant. There's still nothing as bad as "This guy are sick." Though the fakey Olde English of the earlier games may get on your nerves if you go all the way back to the NES versions.)
...
If you can count to nine and I know you can, you may notice that there's a number I haven't really addressed yet. Dragon Warrior VII is the game from the series I was most excited to get back when it came out, and probably my least favorite now. It hails from a time when RPGs' quality was measured almost entirely in play time, and it shows- I put 200 hours into my one and only playthrough of the game (in English, I might add) and have never finished it. It takes at least an hour to solve the inaugural puzzles and fight your first Slime. First time, with no walkthrough and no knowledge of what I was doing, it took me three. It also took the class system from VI, which was already too grindy, and bloated it all to hell. It is definitely a "fans only" affair, and should probably be avoided unless like me you have come to love Dragon Quest with a passion.
But there really is a lot to love. Each of the DQ games has a lot to offer in terms of story, gameplay, and bad, bad puns. If you've been on the fence, Dragon Quest VIII will set you back $10-20 for PS2, and I think it's still the best one for new players.
(With apologies to John Seavey, whose excellent columns at Mightygodking.com inspired this.)
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