Shuffle the tracks
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Player > Shuffle or 
on the Player Window.
Shuffle mode randomly rearranges the track order. If you want to play your tracks in a particular order, turn shuffle off. If you want to play the tracks in a random order, select Shuffle On.
To reshuffle the "Playing Now" Playlist, do one of the following:
- Right click on Playing Now in the tree, and select "Reshuffle".
- Right click on any song in the content-view of the "Playing Now" Playlist and select "Reshuffle".