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I remember reading his blog like 25 years ago and it was pretty interesting. Some funny stories, thought experiments, interesting comments. I remember that he was trying to help some young author get into papers. The idea for comic was solid but drawing wasn't good enough so they organized a competing for artists and blog readers voted. Other time he told people to write phrases that sounded like they mean something but didn't and then made it into a song. Supposedly that's how The Beatles wrote their lyrics. At some point he got married and become a stepfather so he wrote about that as well. Stuff like that. He wasn't that famous, the internet wasn't that big, it was all just for fun.
I stopped following it for couple of years and next thing I know he got divorced, his new girlfriend was 20 something Instagram model and he started writing about how great Trump was. WTF happened?
It's one version of the white guy midlife crisis. They realize they aren't special and it makes them angry and they turn to conservatism for some reason and acclimate to the racism and misogyny they surround themselves with and then them amplify it. It's a miserable pipe line. With trumpers instead of getting the flashy car they get a young, trophy girlfriend. Or both if they have the money. Trumpism frees you from shame.
Seems to be particularly prevalent among celebrities when they fall out of popularity.
In the 90s, he was top of the world, the biggest comic strip, a TV show, and just so much merchandise.
Then in the 2000s, people just kind of got over it. It's not like it became any worse or anything, just everyone had seen it by now, and it just became another strip among many.
So he joined the ranks of other celebrities that everyone just got bored with, like Kevin Sorbo, Kid Rock, etc. When fame leaves them they get all pissy and blame the world.
There are multiple episodes about him on Behind the Bastards, if that helps paint a picture.
https://omny.fm/shows/behind-the-bastards/part-one-how-the-dilbert-guy-lost-his-mind
https://omny.fm/shows/behind-the-bastards/part-one-the-religion-war-by-scott-adams-with-matt
Life broke him I guess.