Arlo Guthrie, who's father was pretty much a Communist, has been a registered Republican for a few years.
It's not that he's a conservative -- he's somewhere between a Ron Paulista and a liberal Republican -- but still, it's something.
He also takes his "kids" on the road with him, and is a very strong family man [also unlike his Dad.] Arlo's trajectory is particularly striking when you consider that all of his influences were Old Labor/Red. He still has a lot of those guys as close friends.