2. Scott Hall
One of pro wrestling's perennial bad boys, Scott Hall's drinking and partying were legendary in pro wrestling circles.
A prominent figure in the Monday Night Wars, Scott Hall jumped ship to WCW after spending years as Razor Ramon in WWE. His final days with that company were often spent on suspension for his poor behavior and propensity to no-show events.
His poor behavior continued in WCW, where his drinking was even turned into a storyline angle. Eventually, Scott Hall was released by the company, and when WWE chose to restart the NWO after the collapse of WCW he was not invited to join them.
Hall would go on to work for TNA, but he still had his issues. After no-showing a PPV where he was to team with Kevin Nash and Samoa Joe, it seemed he had used up his final chance and was fired.
These days he works behind the scenes and seems to have finally conquered his demons. While Hall has had a great career in spite of his issues, he never held a world championship, which would almost certainly have happened if he'd been able to keep his behavior in check.