I figure this is warped, twisted and borderline ASB, but also fun.
Jim Morrisson, Jerry Garcia, Janis Joplin or Jimi Hendrix as President of the United States.
Bonus points if they can be on the same ticket.
They have to have had something resembling their music career (say 3 albums before POD). They can also have their beliefs evolve but no sudden shifts, like "one day, Jimi woke up a Republican Evegangelical and the face of Nancy Reagan's 'Just Say No Campaign'."