A system is presented providing content to a plurality of handheld devices (including musical selections). The devices can access a server over the Internet via a Wi-Fi or other similar wireless interconnection and can download songs requested by a user from the server or from other users using, e.g., a P2P protocol. All downloads may be governed by applicable DRM rules. Content and playlists may also be pushed by a server from other sources and means including, e.g., podcasting, based on predetermined rules, favorite preferences of users, and other criteria.