alt Hacker NewsStory 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.
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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
"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