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.
There was a good documentary about this on Netflix that talked about how he was seen as one of the only well known figures of that era that transcended the culture war but because he’d never made his political views known publicly until that time Nixon could plausibly believe that he was conservative or at least could be useful as a political tool. It’s kind of similar how to very early on in the Colbert Report some conservatives didn’t realize he was playing a character which could plausibly explain his invitation to host the White House press correspondents dinner.