Problem with playing music as the alarm

OK ladies and gents - if someone can help me I'll be much greatful!
So we've tried a whole bunch of stuff already and it could be that the **** iPod has a glitch. We shall see...
So we have no problem getting the alarm to work, we can even get it to play music but it'll only play the first track in the song listing or the last track played. This would be ok but if I want to go to sleep listening to one thing and wake up to another it's not all that helpful!
We've set up on-the-go playlists and iTunes playlists and they don't work any differently.
We were using third-party software which we thought might have been messing with it, so we formatted it and ungraded the firmware and still having problems.
We've tried the trick of turning the alarm off and on after reselecting the playlist.
Who's the man?
Thanks
PC Windows XP

Yes sorry I didn't explain very clearly.
We want to play music as the alarm. But each time we set it it goes off with the first track listed in the complete songlist, rather than the first song in the selected playlist.
As listed above are all the things I've done to try to resolve it, but they haven't worked.
Maybe the iPod is defective, I can't say until I cover all the bases.
Thanks for the help!

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