Well, for the ps2, you really only have two choices, FFX and FFXII, since XI I don't even consider a part of the series being an MMO and barely average (FFX-2 wasn't very good, and you would need to play X first anyway). Out of those two choices, it's up to you, they are VERY different games in terms of their story and gameplay. A lot of people will tell you XII sucks etc., because it is a lot different from most other FFs. It's a great game, but if you want the one that is more similar to FF1-9, get X. I suggest getting both though, and if you want to get some of the older ones for the ps1:
Final Fantasy Anthology (FFV and VI) - Probably the best available for me, since I think FF VI is the best FF game there is along with Tactics. FFV is ok, but not amazing.
Final Fantasy Chronicles (FFIV and Chrono Trigger) - Another great one. Final Fantasy IV is a great game and was a major turning point for the series, especially in the US, since it was only the 2nd one released here at the time (FF2 and 3 were Japanese only till released on the GBA and DS, respectively). However, the main reason for this is Chrono Trigger, which, along with FFVI, is easily the best SNES game I played.
Final Fantasy VII - You shouldn't let the fact the graphics are dated (even more dated than the SNES ones, since those have a retro-charm about them, being 2D). It was definitely the turning point toward ushering RPGs into mainstream. Yes, the biggest part of this was the graphics at the time, but many people realized that they could enjoy a great story in a video game, and this was the game that started that for a lot of people. Also, aside from the SNES FF, this one has the best magic system so far (I prefer pure classes, like Paladin, Black Mage, White Mage, etc. from FFIV, or the magicite system from VI, but after those two, materia was my favorite). Main downside to FFVII now, you will have to pay $100-200 for it, unless you are really lucky.
Final Fantasy VIII - Graphics will still look dated, but they stand up now far better than FFVII does. Another great game, and I enjoyed it near equally with FFVII, except the characters aren't quite as memorable. The storyline I think is better than VII, so it evens out.
Final Fantasy IX - A lot of people felt this was a step backwards after VII and VIII, but the graphics (I only mention graphics on all these because you did in your opening post) are semi-cartoony so they stand up very well today. I enjoyed this FF a lot, it wasn't as deep and "emotional" as FFVII or VIII, but it was a lot of fun with some very likable characters and I thought a good, albeit semi-generic, battle system. The story was good, but not "epic" in the sense it didn't seem as large scale as previous FFs.
edit: Oh, forgot to mention:
Final Fantasy Tactics (the ps1 version and psp rerelease, not the somewhat silly Final Fantasy Tactics Advance, although it was decent too)- Next to Final Fantasy VI, hands down the best to me. The storyline is somewhat complex, but it is very good. I love the turned-based strategy gameplay and the job system is amazing, and wish they would bring it back. The music is also some of the best, right there with FFIV and VI (the orchestra versions of IV and VI, which obviously aren't in SNES games).
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