In some embodiments, a first electronic device, during a playlist mode, displays a plurality of representations of content items available on the first electronic device. While in the playlist mode, the first electronic device optionally receives a first input, via one or more input devices, selecting a respective representation of a respective content item from the plurality of representations of content items. In response to receiving the first input, in accordance with a determination that the respective content item was playing on the first electronic device when the first input was received, the first electronic device optionally transitions to a now playing mode. In accordance with a determination that the respective content item was not playing on the first electronic device when the first input was received, the first electronic device optionally plays the respective content item on the first electronic device while remaining in the playlist mode.