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February 3rd, 2013, 10:07
Why not play them in more or less chronological order?

Ultima 1-5. I wouldn't bother with 1-3, though.
Might&Magic 3
Ultima Underworld
Ultima VII - The Black Gate
(Darkside of Xeen)
Ultima Underworld 2
Ultima VII: Part Two - Serpent Isle
Cloudside of Xeen, or World of Xeen in one go
Baldur's Gate
Might and Magic VI
Planescape: Torment
Deus Ex
Baldur's Gate 2
Arcanum
Gothic II
Eschalon

And as Shaf suggested, wait for the remakes of the Realms of Arkania games.

Some of the games, especially Ultima Underworld, are easier to enjoy if you are already in "retro mode". Going from Skyrim to UU can be rough, but going from the early Ultimas and MM3 it's another matter.
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