Story of our times: Gen-X counterculture jerk grows up railing against The Man. Grows up, gets rich, famous, becomes The Man. His mind, however, is stuck in the past, still thinks he's a rebel, still thinks he's railing against The Man. In reality, he has become a sadistic asshole hurting others for his self-righteous pleasure. But no amount of pain inflicted on others will make him feel good, he dies a miserable crank.

Adams, Musk, Andreesen, Stephen Miller, Chappelle, Maher. They're everywhere.

"Once you wanted revolution

Now you're the institution

How's it feel to be the man?

It's no fun to be the man."

- Ben Folds, "The Ascent of Stan" https://www.youtube.com/watch?v=caCuRqedslY

So true! And Maher is probably the worst of the lot.

While a little reductive and caricatured, as a Gen-X counterculture type myself I can confirm that there's quite a bit of accuracy in this comment. And a lot more examples in more boring parts of the world than these famous people you are mentioning.

With that said it's not exclusively a Gen-X thing to go from counterculture to establishment while preserving the same root personality driver of narcissism and selfishness. It's obviously recognizable as the trajectory of the Woodstock generation as well.

I thought there were people whose lives followed that trajectory in many generations, but it's just the one. What a relief! /s