Q: Is there a way I can shuffle a playlist or Smart Playlist. For example if I have a Smart Playlist with the Blues, rather than playing them in the same order over and over (and if it is long enough never getting to the end), can I shuffle it instead. Random seems to do a random selection, but never changes it.

Reordering and shuffling playlists

– Joe

A: There is no option in the Smart Playlist criteria itself to always force the Smart Playlist to be shuffled. As you’ve noted, the “random” setting simply selects a random collection of content for the Smart Playlist—it does not present it in a random order.

If you want your Smart Playlist to refresh with random content, you will need to add additional criteria to trigger a Smart Playlist update, and perhaps limit the selection more effectively. Criteria such as “Last Played” and “Play Count” can be useful for limiting a Smart Playlist’s content and thereby causing it to refresh when you sync with your iPod.

If the question is simply a matter of getting what is already in the Smart Playlist to play in a random order, the normal “Shuffle” settings on the iPod and iTunes itself can be used in the same way that they can for any other playlist. On the traditional iPod models the shuffle option can be found under the “Settings” menu, and the 2007 iPod classic and iPod nano also provide the ability to switch the shuffle mode while playing simply by pressing the centre button on the iPod two or three times until the shuffle options appear.

Reordering and shuffling playlists

For the iPod touch and the iPhone, a “Shuffle” menu option is presented at the top of each playlist that you can select instead of an individual track, or you can toggle shuffle on and off during playback by tapping the album artwork and tapping the small shuffle icon in the top-right corner beside the progress bar.


Reordering and shuffling playlists

In iTunes, the shuffle option can be found on the “Controls” menu, or as the second button from the left in the bottom right corner of the iTunes window.


Reordering and shuffling playlists

Note that in iTunes if you are sorting your playlist by anything other than it’s natural sort order, the “Shuffle” setting will have no effect, as your sort order overrides it. To be able to shuffle a playlist or Smart Playlist in iTunes, you must first sort it by the left-most number column:


Reordering and shuffling playlists

Once sorted by the number column, you can manually drag-and-drop tracks up and down the playlist into any order you like, or you can click the “Shuffle” option to randomize the play order.

Note that any sort order or manual re-ordering you specify for the Smart Playlist in iTunes will transfer to the iPod, including the shuffled order. This may be another option for changing the order of a playlist on your iPod, however the shuffled order in iTunes is static—it does not automatically update between iPod syncs, so you would need to toggle the “Shuffle” option in iTunes on and off each time you wanted to re-shuffle the playlist.

One last point to note: You cannot re-order a playlist while the “Shuffle” setting is turned on. However, if you would like to start with a random shuffled order but make a few manual changes, you can copy the shuffled order to the playlists “normal” play order by right-clicking on the playlist in iTunes, and choosing the Copy To Play Order menu option:


Reordering and shuffling playlists

This will set the normal order of tracks to however they are currently displayed (this works for sorting by columns as well). You can then turn off shuffle and/or return to the default sort by clicking on the left-mosto column heading again—the tracks will remain in whatever order they were in when you selected the “Copy to Play Order” option, and you can then drag-and-drop them up and down in the playlist to re-order them further.


Jesse Hollington was a Senior Editor at iLounge. He's written about Apple technology for nearly a decade and had been covering the industry since the early days of iLounge. In his role at iLounge, he provided daily news coverage, wrote and edited features and reviews, and was responsible for the overall quality of the site's content.