Chessmaster on the Game Boy is basically the portable version of Chessmaster 2000—same solid chess engine, just squeezed into that tiny cartridge. The AI’s decent for a handheld game, though it’ll still wreck you if you’re not careful. I like that it has different difficulty levels, so you can start easy and work your way up without feeling completely outmatched right away.

It’s got that classic monochrome look, obviously, but the pieces are clear enough to tell apart. No fancy animations or anything, just pure chess—which is honestly all you need. If you’ve played the console versions, this one’s basically the same, just more convenient for bus rides or waiting in line. Not bad for killing time when you’re stuck somewhere without a real board.