#1 Big Show (2000) - Eliminated 29th - 4 Eliminations
Over his 20 year history in the WWF and WWE, the Big Show never managed to win the Royal Rumble.
Despite having a decorated career, winning several championships along the way, the Giant never managed the feat during his time. He came the closest at the 2000 Royal Rumble, with the Rock being recognized as the victor, despite the fact that there was video evidence that showed the Rock's feet hitting the floor first.
The Big Show came to the Royal Rumble as the 26th entry, eliminating Test, Gangrel, Road Dogg, and X-Pac, before being left in the final two with the Rock. The Big Show threw the Rock around the ring and picked him up onto his shoulder to throw him over the top rope. However, the Rock managed to hold on to the top rope and seemed to send the Big Show over the top using the Giant's own momentum.
The Big Show would then pitch to WWF Champion, Triple H, that he was the true winner of the Royal Rumble and defeated the Rock for his spot in the title match at Wrestlemania. The Rock and Mick Foley would be added to the match to make it a fatal four-way elimination match.