Years active in WWE: 1988-1993, 1998-2003
Manager: Slick, Vince McMahon
Finishing move: Big Boss Slam
Best heel moment: Dragging the casket of Big Show’s father
Most heels are cocky or arrogant, but the Big Boss Man crossed that line into pure evil. He fed Al Snow his own dog. He wrote a poem insulting Big Show’s dead father. He even showed up to the father’s funeral, hooked his truck up to the casket, and dragged it away from the burial. The video of Big Show, crying on top of the casket as it’s being dragged, has become iconic. The Big Boss Man hit his heel prime in the middle of the Attitude Era; it’s highly unlikely that something like this could ever happen again.