Decades before Rick Ross could even dream of getting dropped by Reebok, Run-D.M.C. broke boundaries—and made serious bank—with a show at Madison Square Garden in 1986. The trio's road manager, Lyor Cohen, in one of his earliest, smartest power moves, invited Adidas exec (and former soccer star) Angelo Anastasio to see Run-D.M.C. performing at Madison Square Garden.
When the group performed "My Adidas," Run asked the crowd to hold their sneakers in the air. The sight of tens of thousands of young fans holding up their shell-toes reportedly brought Anastasio to tears, and led to him convincing his higher ups to sign the group to an unprecedented $1 million deal that included their own signature line. It was rap's first endorsement deal, kicking down doors at a time when most of the world saw hip-hop as a fad at best, and a cultural danger at worst.