#3 Stone Cold Steve Austin (1999) - 2nd - 8 Eliminations
Stone Cold won the 1997 and 1998 Royal Rumble, but he was put in a difficult position when he was drawn the first entry "randomly" by Vince McMahon. On top of this, McMahon put a $100,000 bounty on Austin that would go to the superstar that could eliminate Austin.
After failing to enter himself at the 30th entry, the WWE CEO was forced to enter the Rumble second, leaving the two in the ring for 90 seconds before the next entrant came to the ring. After Golga's elimination, McMahon escaped the ring with Stone Cold in pursuit. McMahon lead Austin around the arena, before leading him into a trap, where Austin was jumped by members of the Corporation stable.
After the attack, Austin was loaded on to a hospital gurney, packed into the back of an ambulance and taken to a nearby medical facility. Later in the event, Austin returned in the ambulance and re-entered the rumble.
Austin would go on to eliminate Ken Shamrock, Billy Gunn, Test, Chyna, Triple H, Owen Hart, and the Big Boss Man before being eliminated by Mr. McMahon. Stone Cold's 56 minutes and 38 seconds was a record for a first entry until Chris Benoit in 2004.