Chessmaster (Software Toolworks, several versions)

Chessmaster is the king of all chess programs, consistently offering the most intelligent and challenging game play of all the chess programs available. Though in most cases, the graphics are simple (though, of course, in the later versions, they become more and more complex), there are many options allowing all sorts of variation in chess play, including the ability to play chess with multiple boards styles, various instructional and informational modes, and, in most cases, the ability to replay famous chess games from ages past. Though the learning mode leaves a little bit to be desired (the computer won't let you beat it, to be sure) and the games are all challenging, even on the easiest of difficult levels, if you like chess, or want to learn to like it, there is no better program available than this.

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