Digital Rights Management (DRM) technology is used to control access to copyrighted digital content. Apple employs a DRM system known as Fairplay in its iTunes online music store. Users communicate with the centralized iTunes server to download, purchase, play, and preview digital content. The iTunes music store has the potential disadvantage of a bandwidth bottleneck at the centralized server. Furthermore, this bandwidth bottleneck problem will escalate with increasing popularity of online music and other digital media, such as video. In this chapter, we analyze the Fairplay DRM system. We then consider a modified architecture that can be employed over existing peer-to-peer (P2P) networks. Our new system, P2PTunes, is designed to provide the benefits of a decentralized P2P network while providing DRM content protection that is at least as strong as that found in Fairplay.