10 Most Disastrous Wrestling Heel Turns

The Charismatic Enigma's otherwise brilliant career has been marred by two disastrous heel turns - and yet something tells you that WWE writers could decide that third time may well the charm when he recovers from injury later this year.

Until then, it's his bizarre character shift in 2003 that stands out as the worst. A few months after nearly toppling The Undertaker in that ladder match on Raw, Jeff began sporting an attitude unbecoming of one of the company's brightest young rookies.

He briefly began feuding with sage ring master Shawn Michaels, but it was clear that he wasn't comfortable wearing the colours of evil. His performances just weren't convincing and, at any rate, real-life concerns around his lack of professionalism saw that the storyline was nixed before it reached its natural climax.

The former Team Xtreme member turned heel again in 2010, this time joining up with Hulk Hogan and Eric Bischoff at TNA's Bound For Glory. The result was largely the same, although it's almost tempting to give them a pass here for how brilliantly shocking the moment itself was.