42. Mr. McMahon

Era: Late '90s to 2000s

When the Attitude Era took hold, Vince McMahon, the uber professional, pastel blazer wearing commentator revealed himself as the real-life, Chairman of the Board of the WWF/E. Turns out the straight laced, Kosel-esque commentator was the gimmick, and the ball-busting, bravado spewing, epitome of the boss you've always wanted to punch in the face, Mr. McMahon character was closer to his true identity. This "turn" not only made him the on-air authority figure/protagonist in every major story line since, but also led to Mr. McMahon competing in the ring in black jeans and a black cut off sweat shirt right out of Rocky Balboa's wardrobe from Rocky 1. You'd think a billionaire could afford nicer ring attire, right? Well, you thought wrong, and now YOU'RE FIRED! -AG