Chessmaster on the Game Boy is basically the portable version of Chessmaster 2000—same solid chess engine, just crammed into that little gray brick. The AI’s decent for its time, with a bunch of difficulty levels so you can go from "I just learned how the horsey moves" to "why is this thing destroying me in six moves?"

It’s got the usual tournament mode and puzzles, but honestly, the real charm is playing against the CPU on a bus ride or waiting for class to start. The graphics are… well, it’s Game Boy chess, so don’t expect fancy animations. Just clean, readable pieces on a tiny grid. If you’re into portable strategy, this one holds up better than you’d think.