10 Wrestlers With Longest Time Between First & Last WWE Raw Matches

The Long & Winding Raw...

Matt Hardy
WWE

The pop generated by Edge's Royal Rumble return wasn't just rooted in nostalgia but the thrill of a former favourite beating the odds.

The man that retired in 2011 did so because he was forced to by the grind of his dream job. A job that rewards longevity outwardly but internally erodes the skin and bones of the men and women that seek to achieve it. This was Edge's story just like it was the story of hundreds of others that have thrown themselves back-first onto thinly-covered plywood for a living.

As the biggest televised stage upon which to do just that, wrestling on Monday Night Raw remains a pinnacle for most, even if they put a quarter of a century between their first and last appearances. And that's what we'll have a look at here.

There's not a lot of rules, and (pleasant) corrections and comments are welcomed below the line, but names and gimmicks will decide the fate of the long-standing stars. And it's about how they started and ended, not the friends they made along the way - K-Kwik wasn't exactly a world away from R-Truth philosophically, but whilst Ron Killings may be ageless, his original moniker was not.

Kane rocked up as a dentist in 1995, but 'The Big Red Machine' didn't wrestle on Raw until 1998, and his 24/7 Championship turn as "Mayor Glenn Jacobs" in 2019 squeezes him out too. Other former holders of that prize were a little luckier...

10. The Big Show - 20 Years, 9 Months, 1 Day

Matt Hardy
WWE

First Raw Match: 13th April, 1999

Last Raw Match: 13th January, 2020

Sneaking in to the top 10 ahead of The Undertaker, The Big Show would have added a few extra months to his record had he not kickstarted his WWE career working as Paul Wight before taking on the more familiar moniker.

Starting as he intended to go on over the next two decades, Big Show had already turned once by the time he actually worked under the name and went to a disappointing no contest with The Corporate Ministry's Viscera in 1999.

The gradual Russofication of Monday Night Raw around that time resulted in hardly anybody even noticing how the matches concluded, let alone the twists and turns that spun out either side of them.

Show was a victim and a symptom of the roster he strolled into, regardless of how well Vince McMahon thought he could book him. He deserves credit for remaining active and athletic enough to still be an occasional physical presence all these years later.

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Michael is a writer, editor, podcaster and presenter for WhatCulture Wrestling, and has been with the organisation over 7 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 30 years. As one third of "The Dadley Boyz", Michael has contributed to the huge rise in popularity of the WhatCulture Wrestling Podcast, earning it top spot in the UK's wrestling podcast charts with well over 50,000,000 total downloads. He has been featured as a wrestling analyst for the Tampa Bay Times and Sports Guys Talking Wrestling, and has covered milestone events in New York, Dallas, Las Vegas, 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