Media Content Based on Operational Data

An example computing system that maintains a playlist of media items for playback by one or more playback devices receives, from a first playback device, a request to play back the playlist and first operational data and also receives, from a second playback device, a request to play back the playlist and second operational data. The computing system provides the media items in the playlist to the first and second playback devices for substantially synchronous playback and, based on the first and second operational data, determines respective first and second advertisements. The computing system provides the first advertisement to the first playback device for playback during a given time slot designated for advertisements, and also provides the second advertisement to the second playback device for playback during the given time slot, such that the second playback device plays the second advertisement while the first playback device plays the first advertisement.