10 Wrestlers Who Were Notoriously Difficult To Work With

5. Ole Anderson

shawn michaels sid
WWE.com

Ole Anderson, to borrow his bluntness, was a miserable sack of sh*t. An incredible heel - incredible - and genius wrestling mind, he was, nonetheless, a miserable sack of sh*t. Those aren't the words of your writer; they are the words of the men who worked with. The men, to a man, that he alienated.

"Nothing makes him happy," Bobby Heenan once said of him. Burying him with his next-level wit, Heenan described Ole as "the kind of guy with a size 10 foot who wears size nine shoes". As booker in Georgia Championship Wrestling, several - countless - performers sacrificed morale for a payday. The original Doink The Clown, Matt Borne, revealed that Ole relished breaking new guys into the business. But not just that: Ole, stretching an already troubling practise, would wait until the greenhorn was on his last legs before knocking them about. What was already euphemistically pitched as something "protective", in Ole's hands, entered the realm of pure sadism.

A consummate pro in the ring, Ole's inclusion differs from the rest. People didn't merely hate him, they feared him. No less a badass than Arn Anderson was intimidated by Ole, who referred to him as "tyrant" - "the one guy I was most afraid of in the wrestling business."

A true heel, you can trawl through YouTube all day long, and you'll not find anybody with a good word to say about him.

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!