10 Embarrassing Times Wrestlers Tried To Look Cool

9. And So Does Triple H

Stephanie McMahon
WWE

More supporting evidence in the "Stephanie McMahon wasn't being self-aware" file - in addition to the fact that her surname is 'McMahon' - is that, were she actually wearing a Kangol to make herself look cringe on purpose, she'd had to have acknowledged that her husband looked cringe by accident two years earlier.

"Darling, you looked a right t*t with that hat on when you were trying to get over as a main eventer - can I use that to look like an idiot?"

Triple H eventually got it, or was given it, four or so years after making his WWF debut. Sh*te gimmick; boring, heat-bereft matches; a very good breakout babyface run overshadowed by the fact that his heel opponent, the Rock, was really the guy the audience wanted to get behind as a babyface: at the turn of the millennium, Triple H was finally undeniable as an elite-tier wrestler. When he fancied it, the man was exceptional at showing ass with his frantic selling all the more effective for how well he built his phases of offence.

After an inadvertently hilarious summer, he almost didn't. The embryonic 'Game' character was fatally try-hard - he was the one who could say "f*ck" on TV, because he was that damn edgy - and with his Kangol hat and hippy-adjacent shades, he didn't know which generation of cool person to look like.

The Franchise-uh instead tried very hard to look like them all.

Contributor
Contributor

Michael Sidgwick is an editor, writer and podcaster for WhatCulture Wrestling. With over seven years of experience in wrestling analysis, Michael was published in the influential institution that was Power Slam magazine, and specialises in providing insights into All Elite Wrestling - so much so that he wrote a book about the subject. You can order Becoming All Elite: The Rise Of AEW on Amazon. Possessing a deep knowledge also of WWE, WCW, ECW and New Japan Pro Wrestling, Michael’s work has been publicly praised by former AEW World Champions Kenny Omega and MJF, and current Undisputed WWE Champion Cody Rhodes. When he isn’t putting your finger on why things are the way they are in the endlessly fascinating world of professional wrestling, Michael wraps his own around a hand grinder to explore the world of specialty coffee. Follow Michael on X (formerly known as Twitter) @MSidgwick for more!