#2 Randy Savage
In terms of legends of the ‘80s and ‘90s, there really is only one or two who can match the Macho Man.
Since debuting with the then-World Wrestling Federation in 1985, Randy Savage would go on to become a pop culture icon by the time all was said and done, transcending the wrestling business itself, whether in the WWF or in WCW.
Savage was involved in five Royal Rumble matches during his time in the WWF, with his elimination by Hulk Hogan in the 1989 Royal Rumble being the catalyst for the Mega Powers “exploding” and feuding over the WWF Championship at WrestleMania V.
Despite being involved in those matches and being such a high profile figure in the WWF during that time, Savage was surprisingly not victorious in a single one of the Royal Rumble bouts that he competed in. The closest he would come to a Rumble win was in 1993, where he would be the last person to be eliminated as Yokozuna won the contest.
The Macho Man is someone who is synonymous with WrestleMania and synonymous with huge matches throughout his career, but Randy Savage is one of the legendary figures who never mustered up a Royal Rumble win in their career.