2. Jeff Hardy
Jeff Hardy is easily one of the most charismatic performers in WWE history. As well, he may also be one of the most most famously injured, hurting and substance abusing performers, too. When it comes to Hardy dropping the WWE World Heavyweight Championship to "Straight Edge Messiah" CM Punk in 2009 and then being arrested 13 days later for having 262 Vicodin prescription pills, 180 Soma prescription pills, 555 milliliters of anabolic steroids, a residual amount of powder cocaine, and drug paraphernalia in his home, well...yeah...a lot of things make sense in the timing of dropping the title.