An electronic device associated with a media-providing service receives a first media item, including information indicating: a first insertion time within the first media item and a second media item to be played at the first insertion time. The electronic device stores the first media item, including information indicating the first insertion time and information indicating the second media item. In response to receiving a request from a second electronic device to initiate playback of a first media item the electronic device provides the first media item to the second electronic device, including queuing the second electronic device to playback, in sequence and without pausing and without user intervention: the first media item until the first insertion time, the second media item at the first insertion time, and the first media item beginning at the first insertion time after playback of the second media item is ceased.