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There is a work-around. Create a playlist. Add your first song to it. Then, double click it in your new playlist. Now, go back to your library and add things to the new playlist as you like.
Sorry. It's not exactly the same, but it's a workaround that will get the improvised-playlist kind of behavior you're looking for.
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-Adam S ... PowerBook G4 (Mac OS X... the latest version, whatever it is, I've got it, dangit) and original iPod (iLove music, therefore iLove iPod)
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