I crunched the numbers on the 2011 playlists for Crap From The Past.
922 songs total.
One song played five times: FRIDAY - Rebecca Black (2011)
One song played four times: WHITE HORSE - Laid Back (1984)
One song played three times: DON'T GO BREAKING MY HEART - ODB and Macy Gray (2005)
22 songs played twice.
Everything else played just once. That's about 96% repeat-free, which is pretty good!