Q: Is there a way to pick what order your songs play in on an iPod shuffle in normal play mode? Right now it sorts it by artist.
A: The iPod shuffle works a little bit differently from its larger-sized kin in the way that music is transferred and organized. Basically, when placing music on an iPod shuffle, you’re really just managing it like one big playlist of its own. You can therefore change the sort order of the music on the shuffle by any of the normal columns that you would sort a playlist by.
Simply connect your iPod shuffle and select it in the left-hand source pane in iTunes. You will see the normal summary screen, but at the top will be a tab to select “Contents” – simply choose this tab and you will see a list of all of the tracks on your iPod shuffle. To change the play order, simply choose one of the column headings to sort your tracks in that order.
Further, if you select the very left-hand column, this will return the content to a normal unsorted order. You can then drag-and-drop tracks into any order you prefer simply by highlighting a track and dragging it up or down in the playlist order.
Once you have the playlist on the shuffle organized in the way you’d like, simply right-click the shuffle in the source tree, and choose “Sync” and this play order will be transferred to your iPod shuffle.