I do much the same thing. I worked as a radio announcer for over a decade and I've collected a ton of crap. I've created a GOAT playlist in iTunes, 1724 songs lasting 4.6 days. Mostly classic rock, oldies and blues, but I throw in a load of other stuff from popular genres.
I pause the playlist during breaks because I have my tournament timer set to play 15 minute mixes of music that I've taken from the Oceans films, complete with reminders to return from break.
Hint: Audio Hijack is a wonderful little program for collecting songs.
PS - Norman Chad will do some really cool custom stuff for your tournaments on Cameo.