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Jack “Space Monkey” Dorsey

Photo: Andrew Burton
Photo: Andrew Burton (Getty Images)

Our shiny CEO shows some(?) sort of human emotion. This was taken in 2013, on the trading floor the night Twitter had its stock market debut. The platform was enough of a cultural phenomenon at this point that the IPO turned into a media event, too—this was the first time that the New York Stock Exchange ever livestreamed a company’s IPO. And what better way to commemorate this massive career milestone than paying homage to the buzz cut Brad Pitt was rocking towards the end of Fight Club.

Before you fire off an angry comment about how that shaved scalp “definitely isn’t an homage to anything” and that “dude was probably just being comfortable under all those fluorescent lights”—I know. Let me have this. 5/10.