Chex if he is into sports and hockey then get him NHL 2001. The game is absolutly a blast to play and with great graphics too.
If you don't care about Violence - go for Unreal Tournament. Also, Counter-Strike (retail version) might be out by then, which is great too if he doesn't have Half-Life.
Need for Speed is fun in the racing department. I had Midtown Madness and I really did not enjoy it. Got so boring ...
I heard Grand Prix 3 is good, but thats like Cart Racing, which probably gets boring.
Civilization II is an old but great game, I've never played Command and Conquor but I heard it was good as well ...
Also, if you want to pull out the big bucks go for the dreamcast. Forget the PS2 Hype, the dreamcast has solid graphics with tons of games for only $149 (compared to the PS2's 300 bucks)
I currently play games like Tony Hawk Pro Skater (with 2 coming out soon) and NFL 2k1. The games are a blast to play and it is a great console if your going to spend the money.
NHL 2001 is the bomb, I recommend it too. He's also right about the PS2 hype.. It's not worth searching endlessly until next year, when you can go down to any local electronics store and buy one easily. The Dreamcast has a lot of great games, and a ton lined up.