Supreme Mike Tyson 2007 Tee

After two rap-themed portrait tees, Supreme looked to James Jebbia’s beloved boxing for its next subject. Mike Tyson dominated heavyweight boxing from the late ‘80s-‘90s and was never shy of controversy throughout his career.

Born in Brooklyn, Tyson was the third New Yorker to be featured for the Supreme portrait series, but the tense shoot actually took place in a Las Vegas hotel room and casino.

With its lack of a conventional portrait pose, the edgy image remains one of the most iconic in the series.