Ranking EVERY WWE Royal Rumble's Biggest Surprise 1988-2022

29. 1999 - Mr McMahon Wins!

Edge Royal Rumble
WWE.com

With money hanging over the head of 'The Rattlesnake' at 1999's Royal Rumble, Vince McMahon the booker seemed to know that the true surprise wasn't in Steve Austin three-peating, but in just who would stop him and claim the bounty.

That he managed it (and that it worked so well), was an audaciously brilliant bit of booking - not only did it create a new obstacle for Austin to overcome, but did away with the idea that McMahon couldn't theoretically end up as the physical opposition for his nemesis. They'd double down on that at St Valentine's Day Massacre a month later.

Contributor
Contributor

Michael is a writer, editor, podcaster and presenter for WhatCulture Wrestling, and has been with the organisation nearly 8 years. He primarily produces written, audio and video content on WWE and AEW, but also provides knowledge and insights on all aspects of the wrestling industry thanks to a passion for it dating back over 35 years. As one third of "The Dadley Boyz" Michael has contributed to the huge rise in popularity of the WhatCulture Wrestling Podcast and its accompanying YouTube channel, earning it top spot in the UK's wrestling podcast charts with well over 62,000,000 total downloads. He has been featured as a wrestling analyst for the Tampa Bay Times, GRAPPL, GCP, Poisonrana and Sports Guys Talking Wrestling, and has covered milestone events in New York, Dallas, Las Vegas, Philadelphia, London and Cardiff. Michael's background in media stretches beyond wrestling coverage, with a degree in Journalism from the University Of Sunderland (2:1) and a series of published articles in sports, music and culture magazines The Crack, A Love Supreme and Pilot. When not offering his voice up for daily wrestling podcasts, he can be found losing it singing far too loud watching his favourite bands play live. Follow him on X/Twitter - @MichaelHamflett