#4 Randy Orton (Didn't Work)
This is only referring to Orton's 2004 face turn as his 2010 and other face turns were successful to some extent. So coming back to the topic, Randy Orton joined the heel faction Evolution in 2003. He soon adopted the "Legend Killer" gimmick and feuded with some of the best veterans such as Shawn Michaels, Chris Benoit, Mick Foley etc. Orton was bound to succeed but his success came quite early. At Summerslam 2004, Orton defeated Chris Benoit to become the Youngest World Heavyweight Champion at the age of 24.
Orton was betrayed the next night on Raw by his Evolution stable-mates and he turned face in the process. Although it looked like he would succeed as a babyface (based on the crowd reactions), it soon started becoming evident that Orton worked best as a heel. He turned heel and became the Legend Killer once again during the Wrestlemania 21 season when he started feuding with The Undertaker. Orton's popularity causes WWE to turn him face time and again but he fails to work as a face every time due to his natural heel characteristics.