With a PoD no later than the first Grammy awards in 1959, have someone win a Emmy, Grammy, Oscar, and Tony and then later be elected President of the United States. Bonus points for any other awards you can throw in there.
I think Henry Fonda could make it work if he won for Grapes of Wrath in 1940, proceeded to have a strong career in film and theatre, and got more involved in politics than he already was OTL (he was a staunch Democrat and did ads for Kennedy). I could see him being a running mate of someone like Humphrey, and then he's a heartbeat (or an election cycle or two) away.
Matthew Broderick and Tom banks have done theater and can win all the other requisite awards but both are too liberal too win potus... The problem with an Emmy is if the tv show is good it will suck up their time for ten years
Best I can come up with is ll cool j or Justin timber lake since they are regular dems and not into Scientology like will smith
So have ll win a Grammy for one of his early hip hop albumins. Give him Cuba gooing jrs role in Jerry McGuire an have him instead of Lawrence fish burn in csi (too speed up his tv career) then let him take up whatever play after retiring from csi. Then he is still young enough to play politics