#1 Randy Orton (2009) - Winner - 3 Eliminations
Despite being a third generation superstar, a member of the impressive Evolution stable and a multiple time World and WWE Champion, it was still 7 years into his career before 'The Viper' Randy Orton won his first Royal Rumble.
Despite having several successful gimmicks before 2009, including the Legend Killer gimmick, it wasn't until his run as the leader of the Legacy stable alongside fellow multi-generational superstars like Cody Rhodes and Ted DiBiase that he would win the Rumble.
Coming out as the 8th entry, one after second-place finisher Triple H. Orton would dominate the Rumble alongside his stablemates Ted DiBiase, who came out as the 10th entry, and Cody Rhodes, who came out as the 15th entry. With the last four coming down to the three members of Legacy against Triple H, it was still impressive that Triple H was able to eliminate both Rhodes and DiBiase before Orton managed to eliminate him.
During the Rumble, Orton only eliminated two competitors aside from Triple H, Big Show and Kane, whom he eliminated with the help of Rhodes and DiBiase.