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July 14, 2025

Roasting the worst tech billionaire haircuts

In 2018, Drew Magary wrote a hilarious piece for GQ about bad conservative hair. Since then, I’ve often wondered if anyone was going to write about bad tech billionaire hair—but sometimes, if you want something in the world, you need to do it yourself. Here we go.

Elon Musk

Elon Musk smiles awkwardly while standing in front of a blue curtain. Image via https://www.dvidshub.net/image/7132409/usafa-hosts-elon-musk

This photo should be included as a caution on every hair plug provider’s website — your plugs could come out looking pretty good, or they could look like this. This guy has more money than he will ever need, and his hair still looks like this. It’s not as bad as that one time he had the General Zorg/world’s least appetizing cinnamon bun haircut, but just barely.

Alex Karp

Photo of Alex Karp standing in front of a gray background. Image via https://www.flickr.com/photos/192333790@N05/53302457013/

Ah, the last gasp effort of a guy who knows he’s balding to tell everyone “but I have HAIR, you guys!”

Jeff Bezos

Photo of Jeff Bezos smiling awkwardly at a Space Force event. Image via https://www.dvidshub.net/image/3908618/jeff-bezos-visits-laafb-smc

Jeff’s Lex Luthor look is…uh…unexceptional, I guess? At any rate, it’s not as strange and off-putting as his laugh.

Peter Thiel

Peter Thiel smiling and looking at something out of frame. Image credit: Gage Skidmore.

Remember Coach Buzzcut from Beavis and Butthead? Peter Thiel sure does. Anytime someone busts out the stereotype that gay men are more stylish, concerned about their appearance, or something similar, I would like to show them this photo.

Mark Zuckerberg (early 2000s to mid-2020s edition)

Mark Zuckerberg smiling at something out of frame and to the left. Image via https://en.wikipedia.org/wiki/Mark_Zuckerberg#/media/File:Zuckerberg-Jourov%C3%A1_meeting_(2020)_(cropped).jpg

Enough ink has been spilled on Zuck’s godawful Caesar cut, but I’d like to point out that his longtime hairstyle also resembled off-brand LEGO man hair. Compared to this decades-long mistake, his current hairstyle is an improvement. Bonus cringe: if you haven’t listened to his Lil Jon & the East Side Boyz cover with T-Pain from late last year, it’s…really something. Zuck debuted the explicit cover song on his Instagram, complete with a dedication to his wife. SO ROMANTIC.

Larry Page

Photo of Larry Page speaking into a microphone. Image via https://en.wikipedia.org/wiki/Larry_Page#/media/File:Larry_Page_in_the_European_Parliament,_17.06.2009_(cropped).jpg

I like to imagine that Larry asked his hairstylist to “Give me the 2000s Zuck, but with a little more edge” and this was the unfortunate result.

Marc Benioff

Photo of Marc Benioff in a blue polo shirt. Image via https://www.flickr.com/photos/salesforce/52304269299/

This is giving ‘90s Michael Douglas in a big way (exception: the beard).

Marc Andreessen

Photo of Marc Andreessen looking to the right while clasping his hands. Image via https://www.flickr.com/photos/jdlasica/10082059294/

Wilson Fisk? The many unsettling “egghead” sculptures randomly placed around my undergrad alma mater? Or both! No wonder this guy gives off rancid supervillain vibes, especially when he says shit like this.

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