Just who is Vincent Kennedy McMahon? To some he is the sports entertainment innovator and visionary corporate leader of a multimillion dollar company. To others he is evil personified- the manipulative sadistic boss of a corral of WWE Superstars who takes great personal pleasure in making others suffer. Mr. McMahon has achieved stunning successes and experienced humiliating defeats and yet keeps coming back for more. What other boss requires his employees to literally kiss his bare ass on national television? This 2 disc production takes a look back at what caused Vince McMahon to come out of the announcer booth and right into some of the most controversial moments ever seen on television. For the first time ever the onscreen and offscreen intrigues of the world’s most notorious boss are broken down by the people who know the man best. Exclusive interviews with Shane, Stephanie and Linda McMahon, Triple H, Hulk Hogan, Kurt Angle, Eric Bischoff, Paul Heyman, and more.
| Actor | Role |
|---|---|
 Vince McMahonMr. McMahon | Mr. McMahon |
 Steve AustinHimself | Himself |
 Paul LevesqueTriple H | Triple H |
 Stephanie McMahon LevesqueHerself | Herself |
 Shane McMahonHimself | Himself |
 Ric FlairHimself | Himself |
 Hulk HoganHimself | Himself |
 Mark CalawayUndertaker | Undertaker |