I always listen to my ipod on random shuffling by song not albums. Although I have this set I have many songs I never seem to hear in most if not all playlists. On the other hand I have songs that I am constantly hearing making me wish the play order was more random. So a while back I found that you can change the order of playlists as they are stored on the ipod. This little tutorial will show you that and how it can help get more random play out or your ipod or nano. All of this is done through iTunes of course.
Step 1.
Select a playlist on your ipod and make sure that the “PlayCount column” is shown and selected as shown below in red.

Step 2.
Now click the shuffle button a few times making sure that you are toggling between shuffle on and shuffle off. You really only have to do this(turning shuffle off and then on) once. Notice that it changed the order of the songs. Nothing new to you I’m sure.

Step 3.
Now that your songs are shuffled a little differently hopefully more than you originally had them, right click the playlist on your ipod and select “Copy to Play Order”.

Technically speaking this does nothing to change the random play of the ipod, but it has definately helped me in hearing less of the songs I have “randomly” heard way too many times and I hear more of those songs that have been swept in the corners for so long a lot more often.
Don’t forget to check out my new software to get movies and songs off your ipod

Brilliant! Just what i needed.
Thanks a lot!
hi,
can you point me to the sdk for itunes? i am not able to locate it anywhere.