DO NOT USE iTunes! I use an iPod, and iTunes will take over your computer like it tried to do mine.
First it will make itself the default player for everything it can if you use it long enough. Then it also installs quicktime with itself, (which I despise with a burning passion). I also hate the fact that when I transfer songs off my ipod to my computer i have to do it a round-about way and the titles of all my songs are renamed to gibberish. Winamp is great. Lots of options, yet is very small. I like the fact you can have it stay on top of all windows. So you have it in minimal mode, (where the player is just a thin strip with basic features), throw it in the bottom corner, and it stays there while you surf the interweb or whatever.
Plus its got plenty of skins if winamp classic isn't your style.
Get winamp, "It whips the llamas' ass!"