I do wear mine when I ride, but that's because I'm on base and wear the buds facing out under my headband so I can hear cars coming up on me plus I'm on paths 80% of the time.
I have a huge variety anything from:
Gwen Stefani, Coldplay to Metallica (on hills), to some Old school funk....and alot of I know it sounds crazy but Clasical techno remixes from like Bach and Bethoven that last at least 10-13 min per song which is cool.