What defines a true heel is bad guy tactics. Traits such as but no limited to cheating, low blows, heel promos, cowardly acts, bullying, sneak attacks, etc. What ultimately pegs a real heel is the ability to garner heat regardless of how "cool" or "bad ass" they are. This is the reason why, as much as I loved heel Stone Cold, I do not include him on this list.
Honorable mention: Big Boss Man - heel moments: feeding Al Snow his own dog, ruining Big Show's dad's funeral
Edge - The Ultimate Opportunist: A very unique character. He had typical heel moves but what elevated him into an original heel was his character relying on surprises and, no pun intend, seizing the opportunity. Whenever I would be swayed into liking him, he would always piss me off with some surprise. For instance, when he beat Mr. Kennedy for the case I was on his boat. Then he cashed in on the Undertaker and the kid at heart just wanted to kick his ass.
Most heel moments:
-con-chairto on Ric Flair
-cashing in on John Cena and Undertaker
-losing the WWE title and winning the world title in the same night
-entering the triple threat in place of an injured Jeff Hardy at Survivor Series 2008
-stealing Lita from Kane
Undertaker - Lord of Darkness: How do you make a guy the biggest heel in the company? Give him a good feud with the biggest babyface. 1998 he confused the fuck out of fans by being heel one day and face the next. It was obvious he was heading towards the turn but not the way they did it. Not to mention the Ministry was probably the coolest faction of the time.
Most heel moments:
-hanging Big Boss Man
-sacrificing Stephanie
-kidnapping Ryan Shamrock
-The line on SmackDown 8/26/99 "If I lose, everybody loses." Best line of his career
-sacrificing Dennis Knight
Randy Orton - Legend Killer/The Viper: The ultimate scumbag. I'm just going to list his heel moments to explain it all
Most heel moments: Legend Killer
-RKOing Stacy Keibler
-spitting on Mick Foley and brutally attacking him so many times
-telling Carlito that his girlfriend (Trish Stratus) was a bitch and that nobody cared about her retiring
-attacking Hogan while simultaneously trying to get with his daughter
-telling Shelton Benjamin that he's uppity and "that's the problem with you people"
-setting the casket on fire with Undertaker in it
-crashing a car with Undertaker in it
-sneak attacking Undertaker and hitting him with several chairs and an urn
Most heel moments:The Viper
-telling Kelly Kelly that their night together wasn't memorable and he used her
-the many punts to the head
-kissing Stephanie in front of HHH
-the several ambushes and beatdowns from Legacy
Honorable mention: Big Boss Man - heel moments: feeding Al Snow his own dog, ruining Big Show's dad's funeral
Edge - The Ultimate Opportunist: A very unique character. He had typical heel moves but what elevated him into an original heel was his character relying on surprises and, no pun intend, seizing the opportunity. Whenever I would be swayed into liking him, he would always piss me off with some surprise. For instance, when he beat Mr. Kennedy for the case I was on his boat. Then he cashed in on the Undertaker and the kid at heart just wanted to kick his ass.
Most heel moments:
-con-chairto on Ric Flair
-cashing in on John Cena and Undertaker
-losing the WWE title and winning the world title in the same night
-entering the triple threat in place of an injured Jeff Hardy at Survivor Series 2008
-stealing Lita from Kane
Undertaker - Lord of Darkness: How do you make a guy the biggest heel in the company? Give him a good feud with the biggest babyface. 1998 he confused the fuck out of fans by being heel one day and face the next. It was obvious he was heading towards the turn but not the way they did it. Not to mention the Ministry was probably the coolest faction of the time.
Most heel moments:
-hanging Big Boss Man
-sacrificing Stephanie
-kidnapping Ryan Shamrock
-The line on SmackDown 8/26/99 "If I lose, everybody loses." Best line of his career
-sacrificing Dennis Knight
Randy Orton - Legend Killer/The Viper: The ultimate scumbag. I'm just going to list his heel moments to explain it all
Most heel moments: Legend Killer
-RKOing Stacy Keibler
-spitting on Mick Foley and brutally attacking him so many times
-telling Carlito that his girlfriend (Trish Stratus) was a bitch and that nobody cared about her retiring
-attacking Hogan while simultaneously trying to get with his daughter
-telling Shelton Benjamin that he's uppity and "that's the problem with you people"
-setting the casket on fire with Undertaker in it
-crashing a car with Undertaker in it
-sneak attacking Undertaker and hitting him with several chairs and an urn
Most heel moments:The Viper
-telling Kelly Kelly that their night together wasn't memorable and he used her
-the many punts to the head
-kissing Stephanie in front of HHH
-the several ambushes and beatdowns from Legacy