10 Embarrassing Times Wrestlers Tried To Be Funny

2. Riddle Gets The Main Roster Treatment

The Miz Scared
WWE.com

On principle, this is a bad and drastically inept thing to have happened, not that it scans as any great shame post-2020.

Matt Riddle was un-f*ck-up-able - almost a living litmus test for Vince McMahon's descent into objective incompetence. Were he to f*ck up Riddle, you'd know that the WWE rot was truly irreversible. He naturally wore the smile Vince mandates, was in outrageously shredded shape, worked like an ass-kicker, and was far from the "entitled millennial" Vince loathed. Riddle did not give a f*ck about annoying anybody en route to grabbing the brass ring and putting himself forward for the main event.

Vince, at least initially, f*cked Riddle up.

He was presented not as a dumb, endearing stoner but a sh*t-brained moron who could barely complete a sentence. In various attempts at comedy, Riddle pitched various business ideas. Sh*t for brains is right; as a WWE "independent contractor", he wouldn't have been allowed to build his empire of "bronuts", "broghurts" and "fun sticker paper".

A babyface you were meant to like that spent more time pestering wrestlers than fighting them, Riddle has subsequently got over through sheer force of will.

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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!