Sean Penn is, as you said, an actor. He isn't a public figure for any other reason. There are no rallies or donations from progressives to support his idiocy.
Very true. Many actors often suffer from delusions of grandeur. They become so enamored with their own success and so called 'status' in the public eye, that they often develop a messiah complex. And this is true of Penn. But as others have stated, is he really espousing progressive values? I don't think so. Any more than I think Jenny McCarthy is a bastion of progressiveness with her anti-vaccination rants.
For the most part, celebrities are attention whores. They are opportunists that are always finding more inventive ways to gain notoriety. Although not entirely true, many believe in the notion of 'there is no such thing as bad press'. So long as they are in the spotlight, they are still relevant.
To a degree, Trump is also an attention whore. His dialog is not that of a serious candidate; it is the inane ramblings of someone who will say anything to gain attention. From my perspective, he is just entertainment and I don't for one second think he is a viable candidate for president. For now, he is riding high because his boisterous tone and rhetoric is essentially sucking all the oxygen out of the room. And to be frank, I believe the more left leaning portions of our media are thoroughly enjoying the sideshow. It's great ratings fodder for them and it also allows them to point out his idiocy for all the world to see, thereby increasing the likelihood that he will single-handedly implode the Republican primary and assure a Democratic victory in November.
On a side note, the fact that now Trump is playing the birther card with Ted Cruz (much to the dismay of the Tea Party), is one of the greatest acts of political karma I have ever seen.