Johnny Cash was a supporter of Nixon and Reagan who didn't care at all for Clinton. He was certainly not a typical conservative, as he had legitimate care for the underdog.
Cash's drug problems were of such a proportion that he'd have been found out if he ever seriously ran for office.
Citation needed for claims he supported Nixon and Reagan. He played at the White House for Nixon, but ignored his request to play the conservative anthem “Okie From Muskogee” (not even his song) and instead played his blistering anti-war and anti-establishment song that sympathized with the youth protest movement, “What Is Truth.” He also played the similarly progressive “Man in Black” and pro-Indian “Ballad of Ira Hayes.” (At a time when there were a lot of tensions between the Native American community and Nixon administration.) His performance seemed to be more of a bold anti-Nixon political statement than anything.
And again, he supported Carter and Gore in their presidential runs in the 80s. I cannot find any evidence whatsoever he supported Reagan, and plenty that suggests he opposed him. He sure as hell did in 1980, and he opposed the GOP in 1988 as well. Don’t think he made an endorsement in 1984.
The drug thing is more of a legitimate issue, but I can see Cash in this timeline turning it into almost a strength of sorts by claiming he was a changed and better man thanks to his faith.
You might want to check out Cash's live performance of "Peace in the Valley" live from the White House. He clear as day voices his support for the President, who he credits for ending the war, and then says its patriotic to stand behind the President regardless of party. He was smart enough to not make any bold and directly political statements for anyone up until Jimmy Carter, but he clearly liked Nixon even if he didn't publicly endorse him.
I will concede that he probably didn't like Reagan all too much. But then again, nither do I.