We usually throw on a pair of micro shades when we’re trying to make our friends laugh. But in 1999, Pitt grabbed a pair of micro shades and rocked them. 1999 was the year of The Matrix, and even though Brad Pitt didn’t star in the film, he made it look like he did. For a maximum look, he topped the shades off with a completely black outfit. In the photo, he’s even flicking his wrist like he owns the place. Maybe he does (via GQ Magazine).