Unfortunately I have never played the first two. Also a few games in the middle never made it to the US so my knowledge of the series is incomplete.
For what I do know:
Tales of Symphonia(Gamecube): Excellent game. Probably the best JRPG you'll find on the Cube. Graphics are outdated nowadays obviously. While it follows some standard tropes it has a fun battle system and the characters are honestly likeable.
Tales of Symphonia 2(Wii): Sort of like having Final Fantasy X-2 in the sense that it's a sequel in a series that the games are usually independent of each other. Not as good as the first one, I never did get to the end of it. It's not a bad game but it's very average.
Tales of the Abyss(PS2): A fun and pretty game. Some people love it, some hate it. Anise is hillarious. The main character tends to be disliked by the fanbase I've noticed although to be fair, in game it does have a valid reason for his somewhat annoying personality. One of the other characters even calls the others on it when they b***h about his personality(which did cause the death of a town, granted on accident).
Tales of Vesperia(360/PS3): A beautiful game, follows the usual Tales approach of an active battle system. The main character unlike in most games is a competent individual who sometimes indulges in vigilante justice to handle problems.
Tales of Legendia(PS2): Don't bother. It sucks. In every way. Battle system is actually a downgrade, characters are not likeable, and the story is meh.
Tales of Graces f(PS3): Which actually surprised some of us when it came here to the US. We were thinking it wouldn't make it. It's funny watching it take apart some standard tropes at the start while still following some other ones.
Honestly you should probably start with the first two Tales games as they're what started it all, but alas, I can't help you there. After those I'd suggest Tales of Symphonia as it seems to be the most popular of the ones released in the US.
One thing to note about them, is that they all use a cartoony anime style as opposed to the realistic anime style that some JRPGs(recent Final Fantasies, Parasite Eve, etc) have been going for. Usually(but not always) the villain isn't a "pure" villain as he usually has a motive for why he's doing the apparently evil thing he's doing(sometimes he really is a jerk though). To borrow TV tropes, the main villain is usually a well intentioned extremist. The series nearly always leans more towards the optimistic side of the sliding scale of cynicism versus optimism(obviously the well intentioned extremest nearly always disagrees with the PCs although in one or two games they do successfully convince him in the end to see things their way).
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