I had to rebuild my computer about a month ago, and I usually just put iTunes on shuffle, so all I've got is a couple hundred songs with a play count of 1.
yeah, i listen on shuffle most of the time, so i can't play. but five lucky songs out my 7,000 have received the most plays:
she belongs to me - bob dylan
technique street - the homosexuals
neutron lover - the homosexuals
perfume-v - pavement
reuters - wire
but that's probably just because those albums were some of the first i put on.