Every Heel WWE Royal Rumble Winner Ranked From Worst To Best

3. Shawn Michaels (1995)

Ric Flair Vince McMahon Charlotte Flair
WWE.com

A stellar performance that would have babyfaced anybody else on the night had it not been performed with Shawn Michaels' typical psychological excellence, the 1995 Royal Rumble might have been reduced to 30 minutes but 'HBK' masterfully obscured it when the company needed it most.

A barren Rumble featured Michaels and The British Bulldog going end-to-end with some disparate dross in between, but a heel victory had never felt so in keeping with the continuity the 'Heartbreak Kid' had built up over two strong Rumble showings.

1992's was his first night on camera as a newly-minted heel, whilst 1994's final four appearance showed his wily aptitude for such a concept. The win felt earned, not least considering the icing on top of a WrestleMania cake. Pamela Anderson as the uncomfortable valet for sh*thouse sleazeball Shawn was quality wrestling shmaltz that was paid off neatly when she defected to Diesel's corner at the 'Show Of Shows' itself.

Contributor
Contributor

Michael is a writer, editor, podcaster and presenter for WhatCulture Wrestling, and has been with the organisation over 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. Within the podcasting space, he also co-hosts Benno & Hamflett, In Your House! and Podcast Horseman: The BoJack Horseman Podcast. He has been featured as a wrestling analyst for the Tampa Bay Times, Fightful, POST Wrestling, 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