I've won a few oddball things via the radio. I once won a "collectors edition" live recording of a David Bowie concert from Nassau Coliseum (1976). It was supposedly for members of the David Bowie fan club, but was really a bootleg,,,and a great one. I also once won the right to have a DJ make any announcement I wanted on New Years Eve over the radio. I remember the friends I greeted because they are still married...many years later.