Chessmaster on Game Boy is basically the portable version of Chessmaster 2000—same solid chess engine, just crammed into that tiny gray brick. The AI’s decent for its time, with different difficulty levels that actually make sense (unlike some chess games where "easy" still crushes you in five moves).

You get the usual modes—play against the computer, two-player hotseat, or just set up custom boards if you want to practice openings. The graphics are… well, it’s Game Boy chess, so don’t expect fancy animations. But the pieces are clear enough, and honestly, that’s all you really need. It’s the kind of thing you’d toss in your bag for long car rides when you’re sick of Tetris.

Fun detail: the manual actually teaches you chess basics, which was clutch back when you couldn’t just Google "how to not suck at chess." Still holds up if you’re into no-nonsense portable chess.