Actually, I think it is a step up when a hollywood celeb type goes for a Libertarian.
They are just confused by the Libe in Libertarian. They know that someone who has the title that starts with libe is for legalizing drugs. They then get tricked by the democrats into voting for the misnomer LIBEral. The drug addled hollwood and rock-n-roll crowd doesn't realize the difference between Libertarians and Liberals. They are easily confused and snowed.
Probably, but business wise it makes no sense for any entertainer to be supporting political candidates in our hyper-partisan times. Why alienate half your audience? Granted, older washed up stars can add a few years to their faded careers by coming out for something liberal - a cause or candidate. It gets them some charity crumbs thrown their way by the socialist Hollywood establishment. So that's one instance where it makes sense, I guess.