The Chessmaster 2000 is the most powerful computer chess program in the world today and the friendliest! It draws from a mammoth opening library of over 71,000 moves - the world's largest. In mid-game, it displays amazing combinations of classical and modern strategy. At end game it calls further upon the world's newest and finest computer chess algorithm to mount virtuoso tactics.
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At the time, this was probably the best chess program you could have bought. Later versions added features and improved AI. I'd say play those. My personal favorite version of Chessmaster is on PS2.