Before I got an iPod I used Winamp to listen to mp3s on my computer. I used Winamp since downloading my first mp3 in 1997 (that’s right, I’m a trend setter). But you can’t sync an iPod with it and Winamp actually managed to get worse with each release, so I made the switch to iTunes.
One feature that made Winamp great, and inexplicably removed, was enqueue. It let you pick a song to play next without stopping the current song. See another song you want to play after that? Enqueue it too. Enqueued songs superceded the random shuffle or default play sequence. Plus a little number showing it’s place in the queue (line for people not familiar with computer terms or British English). Take anyone that ever used Winamp and they probably loved enqueue.

iTunes has the party shuffle which is similar. But with a slight modification it acts just like enqueue. In iTunes, just go to the Party Shuffle and at the bottom where it says Upcoming Songs, select 0. In your Library right-click a song, and select Add to Party Shuffle. This adds it to the bottom of the list. If upcoming songs is set to anything higher than 0, iTunes will insert random songs for you. Or you can select Play Next in Party Suffle instead to bump the song to the top of the list so it plays next.

It’s to bad about Winamp’s slow demise, but onward and upward!

Seems like a moot point, but Winamp can sync with iPod via a plugin that actually has several features that iTunes lacks. As for enqueue…well…I miss it. But not enough to switch to the massive piece of bloat that iTunes is.
(actually I came across this post looking for enqueue information, heh)
You don’t say. Maybe if I find a version of Winamp 2 I’ll switch, but I doubt the iPod plugin would work on it.