#3 Shawn Michaels (2007) - Eliminated 29th - 4 Eliminations
Shawn Michaels initially retired from in-ring performing after suffering a serious spine injury in 1998. However, Michaels would return to in-ring competition 4 years later in a feud against Triple H.
Michaels' second run lasted 8 years before retiring a second time in 2010. During his second run, Michaels would enter the Royal Rumble coming close to winning his third Royal Rumble on so many occasions.
This includes the 2007 Royal Rumble where Shawn Michaels would enter the match as the 23rd entrant, before being eliminated by eventual winner and wrestler that would later retire him, The Undertaker. During his time in the Rumble, the Heartbreak Kid would eliminate Finley, Shelton Benjamin, Randy Orton, and Edge before the Deadman got the better of him.
Shawn Michaels would still end up competing at WrestleMania for the WWE title as Undertaker faced Batista for the World Heavyweight belt. Michaels would lose his title challenge after losing to John Cena via submission.