Musician Presidents

Jello Biafra lead singer of the Dead Kennedys will most likely be running for Presdent on 2012 on the Green ticket, but there would have to be quite the alternate universe for that t work out.
 
In a World where reconstruction had been done properly Paul Robeson (who would not in such a time line have been as pro Soviet- in OTL it was a reaction to US racism)

Dolly Parton would be interesting - in lots of ways.

I could easily see Robeson running for congress in the 60s.

Parton's popularity would certainly get her to congress.

There are quite a few country singers who could've easily gotten to congress or further.

One I'd like to see IRL, Steve Earle. It wouldn't surprise me to see him run as a Green.

And though he's better known as an actor Floyd Red Crow was a country singer and AIM activist from the 70s on. (He was the chief in Dances With Wolves.) I imagine he'd run as a Democrat for congress right after the film came out.

Also Tom Morello of Rage Against the Machine.

Rappers that could've run but probably wouldn't get elected.

KRS One
Ice T

Rappers that actually might get elected.

Reverend Run of Run DMC
Chuck D
Queen Latifah
 
Dee Snyder could start a career attacking Al Gore during the early Clinton years.

Actually, after the notorious PMRC Hearings (Chaired by Gore), Frank Zappa probably could have run for the house and won his district. His performance in front of the commission was quite impressive. He was smart, articulate and had a better grasp of Constitutional principles than most of the jokers questioning him, Gore included.
 
I'm surprised no one's mentioned Bob Dylan for President.

How about good ol' saxophone playing Willie Jeff Clinton? Maybe you could have him make a recording or two before becoming governor of Arkansas.
 
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