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.