25 Most OUT OF POCKET WWE Attitude Era Moments

As a content creator, it really is hard celebrating the WWE Attitude Era in 2026 - about as hard as Jerry Lawler was underneath the commentary table. There are two key reasons here. 

Firstly, that mine has been drilled - about as much as Jerry Lawler wanted to drill every last blonde who turned up on WWE television. In addition to every last YouTube channel and newz site, WWE itself has exhausted the Attitude Era, the buxom shadow of which loomed over the promotion throughout most of the 21st century. Ruthless Aggression was basically a continuation of the Attitude Era. Attitude Era stars were parachuted into several 2010s WrestleMania events because Vince McMahon was incapable of creating new stars. WWE dedicated hundreds of hours to the Monday Night Wars on its Network in order to brag about its great victory. You get it. 

Secondly, most “out of pocket” Attitude Era moments are simply too crass and offensive to find amusing. You aren’t 14 years old anymore. Chris Jericho’s slut-shaming of Stephanie McMahon is unpleasant, and all too common in today’s real world. The Rock’s pet name for Kevin Kelly was just horrible and alienating to a marginalised and ritually abused community of people. An obsessive Triple H treated racism like a collectathon. 

The goal here is to list and laugh at the few moments that strike a very delicate balance; the skits and the sh*t-talk that meet the definition of “out of pocket”, but aren’t gross for the sake of popping unpleasant people. It was tough. 

But unlike Jerry Lawler in 1993, it got done…

The phrase “rip you a new asshole” is - mostly - a figure of speech. It’s a mere verbal threat. If somebody wants to physically attack you, they won’t actually rive your ass cheeks apart with such force that a second hole appears. They’ll just repeatedly punch you. Or, if they’re a pro wrestler, they’ll hope that you stand there long enough for them to dive through the ropes in order to execute a gentle shove. Because 1997 was the year in which so much new ground was broken, however, D-Generation X took this literally. 

Now, this might seem like typically crass Triple H comedy, but there is at least one more incredible level of cruelty to the gag. 

Michael Cole had only recently debuted for the WWF. Indeed, this was the purpose behind the bit; to give the new broadcaster a belated and ironic warm welcome. But Cole really was new and nervous, and was so eager to impress that he fashioned his goatee beard with surgical precision. Take a long look at that thing. It’s so uncannily precise in an “off” way that it almost looks like 2026 AI. Clearly, an anxious Michael Cole spent a very long amount of time and care in getting his “I’m on TV!” look perfect. Only for D-Generation X to almost literally tear him a new asshole.  

Chyna gave him a wedgie. It looked painful. Triple H decided that it wasn’t enough. Triple H then proceeded to lift the hapless geek so high up in the air that he could execute a slam dunk. His gooch would have looked like Abdullah the Butcher’s head after that. 

Very cruel at the time, but Cole became a bit of a bully himself towards Tony Chimel, so it’s probably fine.