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Originally Posted by Johnny Rotten
I love the WinAmp plugin because it allows me to queue songs very easily. If I could enqueue in iTunes, though, I'd probably stick with that. Transferring songs from the iPod is a nice bonus, though. You can do this with other third-party apps, but I've been using WinAmp for years, and it's free (unlike most of the iTunes competitors).
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Check out the link
Using Party Shuffle in iTunes. Party Shuffle is partially a regular queue, and partly an automatic queue. Hard to explain, but the linked article will give you a better idea.