Sorry for the delay.
I think you need to be clear the difference between a play list, and a list of files. A playlist is just a list of songs. You make the playlist, but as you add each track, it will be added to the list at the end. It's like writing down on paper a list of tracks. Whichever you write down next becomes the next on the list.
But a list of files is just that. The music tracks are listed by Windows. If you burn some of the tracks to CD then the ones you choose to burn will be added to the CD. Explorer will list the files stored on the hard drive or burned on the CD in alphabetical order. If you click any of the column headers in Explorer, eg date created or size, or click the Name column, then the list will display differently. With clicking the Name column the list will display in reverse alpha order.
So, only you can decide what tracks to burn to CD. The computer cannot do that for you. And if you want a completely random list then the only way you can achieve that is to write them all down on little slips of paper, shuffle them, then taking out one at a time and add that track to the list to be burned to CD. But even then the list from the CD will be displayed in a specific order.
Similarly with Playlists. If you want a random playlist, use the same slips of paper.
One option with WMP11 is that for specific playlists to goto Play > Shuffle, and then WMP will play the playlist in a random order.
I hope that helps.
Win XP SP2, WMP 11.
I want to create a playlist in WMP 11 consisting of approximately 900 songs and burn all the songs to 6 CD's, approximately 150 songs per CD but I want the songs completely randomized before and after burning to the CD's. Now, when I burn a playlist, the songs are placed on the CD in alphabetic sequence by file name. Any ideas how I can do this? I had the same problem in WMP 9. I want to create 6 CD's for my car CD player that will play songs in random sequence. I especially want to randomize by artist so songs by a given artist will be placed on all 6 cds randomly and never one after he other.