A software and/or hardware facility enables shop and play remote media using a portable media player. Shopping may include, but is not limited to, allowing a user to identify media and acquire (via download or stream) the media to a portable media player for free or for compensation. The facility, in some embodiments, allows a user to shop for media on a network site or service using a portable media player via a wired or wireless connection. The facility, in some embodiments, automatically presents a user with media available from a network site or service that is related to the context of the user's use of the portable media player, such as when a user navigates or otherwise uses the portable media player. Other embodiments are described and claimed.