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Reagan hasn't been in office for thirty years. What helped him is probably what I said helped Trump; the near absence of any celebrities of note with openly conservative politics. If leftists celebrities ran for POTUS they'd split the vote badly but conservatives can close ranks behind their one celebrity of the age who appeals to them.
If anything my problem is that they aren't as left as I'd like them to be. Milano is shilling for the least progressive candidate in the Democratic primary just like all the major celebrities did when they backed Hillary. She even said "its not about policy."
The right would like celebrities of their own I imagine but their celebrity worship is dampened by the fact that they have almost no celebrities of note to actually worship. This is why, like @carlos cadona pointed out, though many decry the celebrity worship on the left some conservatives are quick to eat up the opinion of any halfwit C-list celebrity who panders to them.
Let's face it, the average American liberal would also be equally as sickened by the celebrities, as the American right-winger, if the majority of them were spouting their pro-life, pro-gun, anti-health care opinions in public, trying to use their influence in order to affect public opinion. It is what it is.
It just happens to be that, today, their careers are furthered by assuming the left-wing platform as their own. So 99% of them are on the left (superficially, atleast). 99% of them are also career-driven air-heads who don't really have a clue about matters of importance.
Under another set of circumstances, they could be holding entirely different opinions. The celebrity caste is such that it basically aligns with what is "main-line culture", because they need public acceptance in order to survive. A wrong move politically, could cost their whole career, alienating key demographics.
In that sense Trump is an oddity since he assumed a bit of a "counter-cultural" position in order to carve out a niche for himself, without any contending challengers. Which in the end has worked for him, but hasn't necessarily helped his "brand". Most celebrities wouldn't take such a risk. Their "brand" is everything to them, and they're not going to screw that up, just because of some political idea.