#1 Kane and Lita
Kane has been depicted throughout his career as a vile and sadistic monster, with some of WWE's most controversial storylines attached to him. He has a tragic background and messy love life, with his first on-screen love Tori betraying him by partnering up with his former tag team partner, X-Pac.
When it comes to Kane’s troubled romantic history, nothing compares to Lita. After his loss at WrestleMania XX, Kane fell in love with Lita, who simply wasn't interested. This led to him kidnapping Lita in May. When she later announced that she was pregnant with Matt Hardy, Kane claimed that he was the dad and that he had impregnated Lita in order to continue his legacy.
Kane defeated Hardy and married Lita after defeating Matt Hardy in a “Till Death Do Us Part” match at SummerSlam. The baby miscarried when Gene Snitsky collided with her. Even though for the next couple of years he maintained that it wasn’t his fault, was caught on camera kicking a baby into the crowd. It was a pretty distasteful display.