Rogan is full of himself. He's also a horrible standup comic. He thinks of himself as some sort of Lenny Bruce/Bill Hicks. A self appointed guru. He's just another example of a Matrix buried Hollywood clown. That said, if he ever wakes up, he would be formidable, and highly influential to countless semi-awakened "Patriot curious."
As to what would it take for Hollywood to wake up? I'm afraid the only solution is mass humiliation and rejection by America proper. Expose the whole rotten system, who they are, what they've been up to. They rank among the worst of the worst in terms of being informed citizens, and should be treated as such. No deals, no compassion.