I want to shuffle the songs on my shuffle with a playlist bigger than 2 gb

Question

I have a shuffle and way too much music for it.  I have a playlist of stuff I would use at the gym but that is still too big.  Can't my shuffle just randomly choose enough song from my playlist to fill itself.  You know "Shuffle" the music.  I had a very old version of a shuffle that did just this every time I plugged it in.
Does anyone know how to tell iTunes to do this?

Answer 1

Yes.  It's called Autofill.
Select the shuffle in the iTunes sidebar, under DEVICES.  If the iTunes sidebar (along left side of widnow) is not visible, from the menu bar, under View, select Show Sidebar.
With the iPod selected in the sidebar, its Summary screen appears to the right.  There is a checkbox for Manually manage music.  To use Autofill, the shuffle needs to be set for Manually manage music.  If you changed that option, Apply the change.
In the sidebar, click on the small triangle to the left of the shuffle name, to drop down it content list, indented below the shuffle.  Click on Music there.  To the right, you see the list of songs on the shuffle.  At the bottom of the list, there are controls for using Autofill.  Select the playlist you want to Autofill from.  Click Settings to get the desired results.