1 Mr. Perfect
Originally was suppose to win the 1990 Royal Rumble until Hogan used his backstage power to change all that. - egnomac
2 Kurt Angle
Kurt Steven Angle is an American professional wrestler, actor and former amateur wrestler currently signed to professional wrestling promotion WWE, where he was the on-screen general manager of the Raw brand and an occasional wrestler.
The closes he came to winning the Rumble was back in 2002 after making to the final two before being eliminated by Triple H - egnomac
3 Andre the Giant
André René Roussimoff, known as André the Giant, was a French professional wrestler and actor. André He most famously feuded with Hulk Hogan, culminating at WrestleMania III, and his best-remembered film role was that of Fezzik, the giant in The Princess Bride. His size was a result of gigantism ...read more.
4 Macho Man Randy Savage
Randy Mario Poffo, better known by his ring name "Macho Man" Randy Savage, was an American professional wrestler and color commentator best known for his time in the World Wrestling Federation and later the World Championship Wrestling.
The closest he came to winning was in 1993 got eliminated by Yokozuna after he awkwardly launched him self over the ropes. - egnomac
5 Ted DiBiase
Theodore Marvin "Ted" DiBiase Sr. is an American former professional wrestler, manager, ordained minister and color commentator.
Made it to the final two in the 1989 Rumble was eliminated by Big John Studd. - egnomac
6 Rowdy Roddy Piper
Roderick George "Roddy" Toombs, better known by his ring name "Rowdy" Roddy Piper, was a Canadian professional wrestler and actor.
7 Ultimate Warrior
Warrior was an American professional wrestler, who most famously wrestled under the ring name The Ultimate Warrior for the World Wrestling Federation from 1987 to 1991 and again in 1992 and 1996. During his 1998 stint in World Championship Wrestling, he was known as The Warrior.
8 Booker T
Booker Huffman Jr., better known by his ring name Booker T, is an American professional wrestler, promoter, and color commentator who is currently signed with WWE as part of the pre-show team on Raw.
9 Rick Rude
Richard Erwin "Rick" Rood, better known by his ring name "Ravishing Rick" Rude, was an American professional wrestler who performed for many promotions, including World Championship Wrestling, World Wrestling Federation, and Extreme Championship Wrestling.
10 Jake The Snake Roberts
11 Eddie Guerrero
Eduardo Gory "Eddie" Guerrero Llanes, was a Mexican-American professional wrestler and a member of the Guerrero wrestling family.