Play Chessmaster, The on gb Online

Chessmaster on the Game Boy is one of those rare ports that actually works better in handheld form. No fancy animations or lengthy tutorials—just you, a tiny screen, and some surprisingly tough AI. The first time I booted it up, I figured I’d breeze through the beginner bots, but that medium-difficulty CPU wiped the floor with me in like six moves.

What’s cool is how stripped-down it feels. Later versions added all these bells and whistles, but here, it’s just chess. The controls are simple (d-pad to move, A to confirm), and the AI scales from "I’ve never played before" to "I might throw my Game Boy across the room." Perfect for killing time on a train or when you’re supposed to be sleeping.

Also, the music? Weirdly intense for a Game Boy chess game. Like someone composed a dramatic symphony for pawns. Still catches me off guard sometimes.