
#1.) Randy Orton
Randy Orton is a superstar who has a lot of unsuccessful experience as a babyface. He first turned face properly in 2004 after Evolution turned on him, but what should have been his breakout moment turned into a reality check as fans failed to get behind The Legend Killer. It was evident that he was a natural heel and over the course of the next decade and a half, he would have multiple runs as a babyface, all of which ended in a heel turn.
The period between 2015 to 2017 saw Orton have a run as a babyface but he was clearly stagnating and he himself admitted to being a much better heel.