I enjoy the Final Fantasy series (although not as much as I enjoy the Dragon Quest series-to me DQ VIII is the difinitive J-RPG of last console cycle). The PS2 Final Fantasies were pretty good, but I would never see myself replaying them (I can't speak for XI as I have the PS2 slim, therefore no harddrive). Instead, I would recommend Final Fantasy IX for the PS1 if you don't mind picking up a PS memory card (which, last I checked, cost about as much as a couple of packs of gum). It's still easy to locate for 10-15 dollars on Amazon (as opposed to something like VII, which would cost you your first born child).
Final Fantasy IX is the only "modern era" Final Fantasy that I have played through multiple times and pretty much enjoyed every minute of it. The characters are entertaining and diverse, if not somewhat stereotypical (but in a good way). Tidus (X) and Vaan (XII) reminded me too much of some metro j-pop star, and Cloud (VII) and Squall (VIII) got to be too broody for me after awhile. Zidane (IX), however, is all about living life and just having a good time. The interactions between him and the rest of the cast are some of the most entertaining moments of any RPG (I still laugh at some of the scenes between him and Steiner). The story is meant to be entertaining and fun. It feels much more light hearted than any of the other 3D FF games. It really doesn't suffer from the riskof being overly pretentious like many of the other games in the series.
The graphics are somewhat dated, but they have aged far better than VII or VIII. The use of the chibi art style is wonderful in this game. Its potential is fully realized and is a throwback to Final Fantasies of old. Every character has their own distinct style. Speaking of Final Fantasies of old, this game serves as somewhat of an ending to era. As such, the developers included some fan service and inside references to FF 1-VIII. Not playing previous FFs will by no means inhibit your enjoyment of the game. These moments are few and far enough in between that you wouldn't be missing anything significant. They are more side things that would cause a chuckle out of a longtime fan such as the village of the gnomes (Final Fantasy IV, although the localization team did drop the ball on that one) or seeing Cloud's sword in a store. Nothing major.
Final Fantasy IX is just plain fun. It's my favorite 3D FF in the series. There are many endearing moments in the game that will plain make you smile, which seems to be missing from the other games IMO. The story is by no means a great work of literature, but the characters alone will give you reason enough to want to play through the entire game.
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