25 Most OUT OF POCKET WWE Attitude Era Moments

7. Shane McMahon Is Sick

Shane Stephanie McMahon
TSN

Michael Landsberg loved interviewing WWE Attitude Era stars back in the day. The general thrust of each chat was that Landsberg would ask the wrestlers if they were corrupting the nation’s youth, they would say no, and he’d keep asking again and again until he got them to say something out of pocket. This gegenpress of an interview tactic yielded spectacular results the likes of which Landsberg couldn’t even dream of when chatting with the McMahon siblings. 

Not remotely media trained, and making an ultra-rare venture outside of the WWE realm at a time when they were both snot-green, this was destined to be extremely disconcerting in a very McMahonian way. It was. 

Landsberg broached the topic of breast augmentation surgery. He pressed Stephanie McMahon about what her limits were as a performer. Is there anything she wouldn’t do? 

Steph asked Landsberg to clarify. Not wanting to say it outright, Landsberg asked Steph if she’d do what Debra does. “Puppies,” a flustered Landsberg eventually said. He could not actually bring himself to say “Would you get them out for the lads?”

Steph said she’s not built like Debra. 

It was at this point that Shane, incredibly, went to bat for his biological sister’s sweater meat. “They’re just smaller puppies, that’s all,” Shane said, looking down at Steph’s rack. “They’re cute”. Cute? What? You shared the same womb! You can’t say that. That's insane. What the hell was he thinking?

“My sister doesn’t have tig old bitties, but they’re still diesel,” Shane might as well have said. 

Contributor
Contributor

Michael Sidgwick (Creative Writing BA Hons) is an editor, writer and podcaster for WhatCulture Wrestling. With over a decade of experience in wrestling analysis, Michael was published in the influential UK 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 AEW World Champions Kenny Omega and MJF, and 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!