Foobar2000 is also pretty stable and awesome -- just need to drop in the Facets component & it's a dream. Winamp is a nice memory from back in the Napster days tho. :)
I've heard some good things about it. I'll give it a try. Winamp is timeless because it's so simple and powerful. I loved the play next queue. If I felt like a few songs I could throw them on the temporary queue without interrupting what was going on. Great for playing music for others too.
foobar has similar features its just confusing at first cuz it puts playlists in tabs. super powerful but takes some getting used to. facets is the necessary add-on because it basically gives you a really powerful search whereas by default there is... none.
the other component i use is the ipod manager i forget what its called but you can find it easily. it lets you add/delete songs pretty easily & if you use flac/wav/whatever it can even convert to mp3 on the fly if you set up the encoder right. that way you can keep lossless on comp but have mp3 on ipod without making an mp3 directory
