Bill Maher and Identity
I always enjoy seeing Big Joel work his way around a topic - he never quite takes it in the direction I'm expecting. In watching his latest video about Bill Maher (cw:the video examines a cavalcade of anti-woke talking points) I thought it a good jumping off point for a general point about Bill, and the general class of person I think he represents.
Bill appears to build his political identity around the idea that he's "normal" and that everyone who disagrees with him is abnormal and to blame for the world's ills. As he's got older and less intuitively in line with the contemporary idea of "liberalism" this has made him a conservative in the modern day. Conversely, he also views people like him as fundamentally "normal" as well, a dangerous play for a wealthy media pundit - it leads to him unironically putting credulous weirdos like Joe Rogan and Elon in his camp of "regular people".
I don't think Bill has ever held a belief that took work. He's of a clade of liberals who hit upon some decent views as teenagers, generally an opposition to a dominant conservative narrative, and figured that they were just special little thinkers that intuitively understand what's right and wrong. They're just conservatives with better base assumptions.
The prominence of Bill and those like him is an indictment of a society that prizes opposition to bad things over the promotion of good things.
He's also clearly way too online.
Most of this stuff Joel covers in the video, but I think it's easy to get too focused on the specimen rather than recognising the overall pattern of people who found themselves as prominent (either in the media or their own social circles) self-proclaimed "liberals" who assume that the label of "progressivism" comes from them approving of it. It's a whole class of guy imo.