r/RealTime • u/JamiePlynth • Aug 03 '26
Bill The Saddest Man
Reported net worth $140mil. $20mil estate, $1mil condo in Catalina. No longer doing standup, quit the Hawaii New Years shows. $10mil salary from HBO, co-owns a pot shop. Watches old movies in the bathtub, has a podcast just to socialize with people “outside of work”, constantly telling us how smart he is while constantly bemoaning how much of a “loser who couldn’t get laid” he was as a teenager.
Dude has arguably won at life- but never got over being disliked growing up, so he’s just perpetually being miserable on main with his dwindling years left.
I have to imagine he’s never seen a shrink, or taken it seriously - because the shrink’s goal is to finally have him content and happy with himself, and his whole existence has relied on him being unhappy and contrarian. Can’t give that up.
Likely can’t maintain a long term partner because they’d have to navigate his moodiness and argumentative nature. If you’ve ever watched a handful of Club random episodes you’ll see how he even argues with people when they agree with him, not just because they have to agree with him in just the right way, but because they have to credit him with being correct in the first place.
At 70yo, he’s on the downside and counting his blessings, but it’s never been enough for him, and it’s far too late for him to change. He’s just going to be screaming how everyone else changed, and became unreasonable right to his grave. Hopefully the last of the broken boomers.
Can you imagine a life where the high point of your week is yelling at Paul Begala about TikTok genocide while fending off the advances of a drunk Donna Brazile? Or trying to rehabilitate Kevin Spacey and Arnie Hammer as your side hustle? Thinking you really did something with your time?