Whats the challenge? That was CM Punk's response to Vince McMahon when told he was turning heel for the first time in his WWE career in the summer of 2009 during his feud with Jeff Hardy. Five years later, it is a fair bet to make that CM Punk the self proclaimed Best in the World is one of the best heels to ever grace WWE television. Whether it is the villainous cult leader, the rebellious, subordinate rebel or the deceitful champion demanding respect, he was always entertaining and at his absolute best with the crowd against him. Unfortunately, it seems CM Punk is long gone from the WWE after his controversial exit after the 2014 Royal Rumble and is showing no signs or interest in returning especially after his recent interview where he stated in spectacular Taylor Swift fashion that he was never ever, ever going back to WWE. As much as this may suck for fans, we can still look back on CM Punks career and enjoy the moments where he hurt us, offended us and made us downright want to storm the ring and fight him ourselves. Its hard to imagine that Vince McMahon once doubted the Chicago born superstars ability to get over as the villain as we look back on some of the finest heel moments of CM Punks WWE Career.
Honourable Mention: CM Punk Walks Out On Chicago
CM Punk can do no wrong in the eyes of the Chicago faithful, one of the biggest fan reactions of all time was at Money in the Bank 2011 when CM Punk not only defeated John Cena for the WWE Championship, but he outsmarted Vince McMahon and walked out on the WWE as their champion with a dynamic crowd supporting his every step. Since that day, Chicagos passion and loyalty to CM Punk has always been a hot talking point when WWE heads back to the Windy City (especially after Punks sudden departure). In the summer of 2012, CM Punk had just turned heel and earlier in the night had bested Sheamus in a war of worlds (oh that promo fell apart, fella). Despite his heel status, the fans were still behind him as expected and WWE had to do something to change that. CM Punk came out for a match with Sheamus, only to take a day and leave the arena without a care in the world. A chorus of boos rained down on Punk as he walked out on those most faithful to him, another shining example of just how easily Punk can gage a crowd and manipulate them to an outcome best suited for him. It's a testament to Punk's heel ability that he can turn even his most loyal of followers against him.