Play The Chessmaster Online

Software Toolworks released The Chessmaster for the Nintendo Entertainment System in 1989, a time when the console's library was dominated by action and platforming games. It stood out simply by being a dedicated, serious chess simulation in that environment, offering a quiet, thoughtful alternative to the more frantic titles of the era.

You control the standard chess pieces, moving them across the board with the goal of checkmating your opponent's king. The game's signature mechanics include its extensive 16-level difficulty system, which allows you to find a suitable challenge from a beginner to a brutally punishing expert, and a separate teaching mode that analyzes your moves to point out mistakes. The pacing is entirely your own, dictated by how long you ponder each move against a computer opponent that feels genuinely cunning at higher settings. It feels like a genuine test of wits, a patient and often humbling battle of strategy.