Okay, something similar to my old 'Pop Star President' challenge idea.
Your challenge, should you choose to accept it, is this:
Make an OTL pop star POTUS, however he/she must:
A. Be currently prominent (and alive) IOTL.
B. Have a career in pop music before becoming President.
You have up to 2040 to get this done. Bonus points for a TL, extra bonus points for a detailed one.
AH.Commers, can you do it?