This chapter charts the birth and growth of the demoscene, an online community of digital artists and musicians who create and share real-time procedural artworks. Part of the digital underground, the ethos was, and remains, one of pushing systems to their limits and so became a natural home for chiptune. The chapter begins by exploring the roots of the demoscene in the computer hacking scene of 1970s California, a community who believed strongly that computer software should be free. As software protection systems were introduced to prevent unauthorized copying, highly skilled ‘crackers’ removed them, highlighting their achievements with elaborate audiovisual digital graffiti. Over time, competition to create the most extravagant artwork and music became an end in itself, creating the demoscene. Today, this vibrant community thrives and has become bigger and slicker than ever, although, as some interviewees suggest, in so doing it may have lost some of its countercultural charm.