A good game of Chess is hard to find

Chessmaster, in various incarnations, has had quite a following over the years, but it never was very serious chess; for that, you need Fritz 11, or a very short stack of quality hackers' chess engines (Crafty, Sjeng, GNU Chess, et al.) that work with eboard (which doubles as an FICS client for online play), xboard, Arena, etc.

The Nintendo DS edition is subtitled "The Art of Learning" by someone yclept Josh Waitzkin (you can locate him easily enough on Google, all by yourself), but apparently all he contributed is the ultralite chess tutorial.

However — and this is an important point — the game does play fun chess, offering A.I. opponents dialed back enough to keep a duffer like me entertained. No matter what level you're on, you can find someone to beat with Chessmaster. The A.I.s get tougher as you improve, so there's no danger of running out of someone to play with. If your kid's a chess genius, buy her Fritz 11.

The familiar Chessmaster is the highest-ranking A.I. in the game (ELO 1850), strong enough to beat good casual players.

Buyer beware...! The Nintendo DS edition, seemingly discontinued (?) by Ubisoft, was not worth $30 brand new in 2007, let alone the $119.97 it goes for these days at Amazon.com. I bought a pre-owned copy for $18 at Video Games, Etc.

A good chess engine is hard to find

The free Crafty 21.6 binary for Windows may be downloaded here. You'll need a GUI, either WinBoard 4.2.7 or Arena 1.1, most likely.

Update — Beowulf 2.3 is also free, also interesting and also needs a winboard-style GUI.

WinBoard has been a favorite of mine for years, mainly because it's a Windows version of the old Linux xboard, which hosts GNU Chess.

However, if what you want is a good free Windows chess program, pure and simple, then look at Mayura. The Sjeng engine, included with Mayura, can beat most of you clowns at its default level (expert), but you can dumb it down and beat it handily if you pay a modicum of attention. Another one in this category is NagaSkaki, which can play at the braindead level. I recommend these because they both have clean, pretty interfaces without a lot of chess fanatic clutter, and they can be handicapped against beginners and young children without condescending.

Free chess (as long as we're making lists...)

There's tons of chess software available. My favorite on the Macintosh was Sigma Chess Lite/HIARCS, which was free. The Windows XP freeware I'm playing with (in lieu of anything so good as that) is:

1. WinBoard 4.2.7a/GNU Chess 5.07 is Tim Mann's traditional xboard interface for GNU Chess and other engines. It can play online, as well.
   
   
2. Arena 1.99beta3 is another excellent first choice. Loaded with features, and supports both WinBoard and UCI style chess engines.
   
   
3. Alpha Chess 3.2.4 is on my list because it has a beatable novice mode and looks good onscreen.
   

That's all, overlooking Arasan 9.5, Der Bringer and many, many others. Life is short, for someone who can't play chess anyway.