Looking back at Nintendo’s Game Boy today, more than a quarter-century on from its launch, it is easy to focus on its chunky design and outdated hardware and forget just how profoundly it revolutionized handheld gaming. Together with Tetris, its pack-in game, whose perfect blend of simplicity and challenge made it the Gameboy’s ‘killer app’, it brought portable gaming to the masses. But the Game Boy’s legacy extends even further than this. Its success was largely the result of its creator’s design philosophy, Lateral thinking with withered technology, an approach that used old hardware in innovative new ways. A decade after it launched, the Game Boy was itself reimagined and applied innovatively in a new context as users hacked it and turned it into a portable musical instrument as part of the chiptune scene. This talk explores that journey and the Game Boy’s musical legacy.