10 Worst Simultaneous WWE/WCW Heavyweight Champions

8. The Undertaker/Kevin Nash (1999)

Diesel Hogan 95
WWE

The future 'Big Evil' and 'Big Sexy' were making the most money of their entire careers as the wrestling business continued to boom in 1999, but match quality wasn't at a premium with these two men as the top title stewards across the brands.

Approaching his in-ring nadir, The Undertaker via Vince Russo was a curious concept. Modernised beyond logic from the humanised 'Deadman' of 1997 and 1998, he fully embraced the occult as the scowling leader of the Ministry Of Darkness before having that persona diluted by becoming a goth heavy for Vince and Shane McMahon's Corporate Ministry. It was utter sh*te, and his matches with Steve Austin, The Rock and others - no matter how much money they were making - with didn't remotely transform the perception.

Writing his own reign from a position of power at the time, Nash at least had a faith in himself he didn't feel like could extend to Hulk Hogan and others that held power beyond rationale in WCW. It was a thankless task for sure, but not one he was able to manage. Worryingly, the belt was beginning its descent into Atlanta insanity anyway - 'Big Sexy' didn't have bangers in him, but soon the legacy of that title would be destroyed by bad booking rather than anything happening bell-to-bell.

 
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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