5 WWE Superstars who won the Royal Rumble in their first attempt

#1 Ric Flair (WWF Royal Rumble 1992)

Ric Flair

Coming less than six months after his WWE debut, the 1992 Royal Rumble Match will forever be known as the Ric Flair Rumble. He was an ever-present in the match after entering at number three. Flair was supported on commentary by Bobby Heenan, with this being his finest hour.

Lasting an hour and eliminating five Superstars, The Nature Boy was a deserved winner of the Royal Rumble and as a result, the WWF Championship. The fact that the Rumble was for the vacant world title makes the 1992 edition so fondly looked back upon. The star power in this match was truly astonishing.

Aside from Ric Flair himself, top names like Roddy Piper, Randy Savage, and The Undertaker were part of this Royal Rumble Match. This doesn't even take into account the final sequence which saw Hulk Hogan get thrown out by Sid Justice, before acting like a heel and trying to pull him out. Flair duly took advantage to eliminate Sid and win the match.

It was a memorable end to this incredible match - the first Royal Rumble with actual stakes to it. Ric Flair faced Randy Savage at WrestleMania VIII, but the big money match was between him and Hogan. The two never faced off in WWE, at least when they were both at the top of the industry at the same time.