4. Big Boss Man
If you want an example of the type of job security that was offered during the Monday Night Wars, look no further than the WWE snatching up the Big Boss Man as soon as his contract was up with WCW, just to stick it to them. Mind you, the Boss Mans arrival didnt shift the tide further in the WWEs direction. While it might be argued that he had a good run being a part of Vince McMahons Corporation stable, and a tag title run with Ken Shamrock, one need only look at some of the more infamous moments during Boss Mans Attitude Era run: The Kennel from Hell match vs. Al Snow, dragging the Big Shows dead dads coffin with a car, and being hung by The Undertaker at the end of one of the worst Hell in a Cell matches that wasnt the Kennel from Hell match.