Ok, so we go to Jambo every year, and every year I compile my music into a Jambo playlist of artists that are going to be at the event.
I use Itunes on my desktop, and for managing my Ipod of course, but I also stream my collection to my Xbox on the home stereo.
I do a search of the 28,000 plus songs for a particular artist and change the info of Genre to something like JITH 2010. Then I do a search of all music with that genre and create a playlist in Itunes called JITH 2010. The reason I change the genre is because Xbox doesn't recognize Itunes playlists but it will recognize genres. So I can load up that genre in Xbox and set it on shuffle and I've got hours of beer drinkin' tunes.