I like the Chessmaster series a lot. It has tons of opening, mid and endgame tutorials, a huge database (thousands) of famous games, intelligent computer opponents each with distinct styles and skill levels, and TCP/IP play.
Grandmaster Josh Waitzkin (the subject of the film "Searching for Bobby Fischer") has been involved with every version of Chessmaster I've ever purchased. He is an excellent speaker and instructor. I love watching his famous games and listening to his blow-by-blow commentaries--truly fascinating stuff! I consider it a real privilege to be able to learn from someone like Josh. His work on the Chessmaster series really demonstrates his passion for chess, and his engaging and informative style of instruction makes learning addictive and fun. Highly recommended... and don't forget "Searching for Bobby Fischer" on DVD if you don't already own it!
Drew,
When I was 21, my younger brother challenged me to a chess game. I had never played before and he had. He won.
I hate to loose, so I bought myself a begginers book on how to play chess. I read it then played him again and kicked his butt.
I actually got quite good at it. At one of my previous jobs we had a chess tournament. Myself and another guy, who was playing since he was 6 and ranked played to a draw for 1st place. I can think several moves ahead of my opponnents which I think is key to playing chess well.
Any chess game on the computer has many different levels to play against. Start at the 1st one and work your way up. It's a great game. good luck.