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10 FUNNIEST Wrestling Moments Of The Attitude Era

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10 FUNNIEST Wrestling Moments Of The Attitude Era

I could write an epic tragedy about WWE’s relationship with comedy.

Through the years they’ve had a near endless fleet of some of the most gifted physical specimens through their doors, who have an overabundance of natural charisma, a killer instinct for timing & playing off a crowd, and years of training on houses shows where every day is substitute teacher day. Yet trying to find anything in the attitude era that isn’t “lol women, foreigners & the gays” is like panning for gold in a river of turds.

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The Attitude Era is very exciting, mostly because a hot crowd makes any wrestling show exciting, but it’s also, for the most part, TOO MUCH, MAN. That being said there were some real comedic gems on reflection and, to be clear, this isn’t a list of botches or things that are so bad they’re funny, christ we’d be here all day, this is a list of times where WWE or a wrestler tried to be funny, and succeeded in the actual way that they intended. That eliminates a LOT of competition.

Warm up your chuckle gear, because these are the 10 Funniest WWE Moments of the Attitude Era.


10. And I’m Gonna Get You Too Rhyno (Raw – August 13, 2001)

https://www.youtube.com/watch?v=l3RoNU1xEdk

Ok sure, when you take out slut-shaming, 95% of Y2Js attitude era promos are him just saying the word “again”, but let’s be clear, Chris Jericho’s long-term rivalry with Stephanie McMahon is a thing of legend, mostly because you can tell that they’re actually deeply in love, but since Triple “Billy Zane in Titanic” H is always around and controlling their lives they’re forced to turn that love into hatred.

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It’s actually very nuanced, and if I remember right it was actually booked by Arthur Miller, who originally coined the term ‘Trashbag Ho’ in the Crucible. The pinnacle of their verbal jousting was in 2001 on the August 13th episode of Raw. Therein sits the classic bait-and-switch line, “at Summerslam I’m going to take care of the smelly, greasy, nasty animal… and I’m gonna get you too rhyno” before the next 10 mins becomes a relentless bagging on Stephanie for having cosmetic work done.

It’s borderline stuff, but what really makes it work is Stephanie’s face selling the whole thing. She’s complicit in the bit and her excellently timed outrage sparks major heat. Bonus points for this segment also being the one where Rock shows up and says that Booker T thinks 2+2 is Thomas Jefferson, which is also the only thing from that rivalry that still holds up. And speaking of the great one…


9. But My Name’s Billy (Heat – July 11, 1999)

I really tried to limit myself to having just one entry featuring The Rock, because during the Attitude Era, the man turned out zingers like Mr Kipling turns out exceedingly good cakes. Call me a heretic but I actually think Rock does his best promo work in the ruthless aggression era but that’s another story for another list. There’s a fairly strong contender in the promo rock cut on all 5 of his opponents at Armageddon 2000 where he slaughters Triple H especially, but in terms of someone being absolutely ruined, to the point where it may have done actual career damage, it has to be the promo he cut on Billy Gunn on the heat before SummerSlam 99.

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He pretends to be Billy talking to God, sad about how he absolutely sucks before the immortal response “bob” “but my name’s billy” “IT DOESN’T MATTER WHAT YOUR NAME IS”. Bonus points as well for this being the first time the rock actually used this catchphrase. First and best.

8. DX State of Union (Raw – February 2, 1998)

https://www.youtube.com/watch?v=qloWK0cNVFQ

The Attitude Era was dumb, crass and immature, and no one exemplified those qualities with as much by-god pride as D-Generation X. DX may have gotten less and less funny as the men slipped further and further into dadhood, but their 90s run had some moments that made even the most high-minded of us go, ‘ok you got me’.

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None of them were as good as the DX State of the Union address from 2nd February 1998 where Shawn Michaels, Triple H and Chyna responded to WWE’s network superiors telling them to sanitise their output by politely indicating their genitals. They list off all the words they’re not allowed to say with WWE even showing the rare maturity of understanding that well-timed censorship is funnier than the swearing itself.

Also, it becomes very clear that one of the reasons that DX deteriorated massively is the fact that they lost Chyna, who played the vital role of straight man and did it better than anyone else at the time. 


7. Shawn Stasiak Runs Into Things (Raw – August 13, 2001 & SummerSlam 2001)

It’s not a main event gimmick, but goddamn if Shawn Stasiak didn’t live it. So when the Alliance invaded, Shawn Stasiak came with them, reappearing in WWE years after his previous gimmick of Meat in Pretty Mean Sisters which, spoilers, has not made this list.

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The gimmick this time? Stasiak would try and impress Stone Cold Steve Austin by attacking members of the WWF roster, which normally ended with him interrupting a backstage promo, missing his target, knocking himself out and this is what elevated every segment to absolute genius…the segment would then continue as if nothing had happened.

The pinnacle of this happened with The Rock and WIlliam Regal, himself one of the WWE’s low-key greatest comedians of all time, talking at SummerSlam. Rock asks Regal what he smells when Stasiak shoots past them, smashed into the shutter behind them and the two men move back into frame for the final ‘if you smell what the Rock is cooking.’ It’s an absolute burial, but dammit if he didn’t sell it beautifully, and proof that Planet Stasiak is governed by Looney Tunes physics.


6. Steve Austin Is CEO of WWF (June 14, 1999)

Steve Austin is rightfully known as one of the toughest SOBs in the wrestling business, but an oft-overlooked part of his character is that he’s also one of the funniest. His anti-WCW promos during his stay in ECW are proof enough alone of that.

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Some of his best work took place during one of the weirdest angles he was ever part of, when he briefly took over as WWF CEO in June 99. What followed were several amazing segments of Austin deadpanning his way around Titan Towers and making some changes around here.

There are many highlights, including Austin having a briefcase full of beer, firing a guy for looking stupid, teaching the receptionist to answer the phone with ‘who the hell is this’, and when someone tells him that they’re responsible to bringing Vince his Chateaubriand, he responds “I like a good wine from time to time myself”.

However, the best is Austin taking ‘several zeros from Vince’s salary to Mick Foley’s because he needs help with his medical bills.’ Surprisingly understated comedy chops from the rattlesnake in a year when everything was shouting all the time, and while we’re talking about Mick Foley

5. Mr Socko (Raw – October 5, 1998)

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Mick Foley is famous for bumps rather than punchlines but he’s subtly been at the centre of most of the great moments of comedy throughout the Attitude Era. Spoiler alert: he’s in 3 of the top five. No matter who he was partnering with, being Stone Cold, The Rock or Vince McMahon, Foley’s sheer force of personality steals the scene with every mumbled, tragic, barely audible aside while the louder personalities shout. Case in point, the October 5th 1998 episode of raw.

Vince is in hospital after having his ankle crushed by the undertaker (the previous Raw) and the purest soul in the history of wrestling tries to cheer the chairman up with a host of goodies, including balloons (aren’t they colourful), chocolates (I know you like the sweet stuff) and Yurple the clown (she does a trick with a dog you wouldn’t believe).

Watching actual millionaire Vince McMahon in a hospital gown saying ‘don’t show me any damn trick with the dog’ is a surreal but wonderful sight, but of course the best is yet to come, as Foley introduces Vinnie Mac to Mr Socko. It’s perfect, the way it creeps into shot, the way Foley’s voice cracks slightly when he says Socko, to the moment Vince breaks and growls ‘dammit, leave’. Bonus points to later in the same episode where Austin attacks McMahon featuring the best timed bedpan shot in the history of entertainment.


4. Milkomania (Raw – August 20, 2001)

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During his active years, Kurt Angle was everything the WWE ever needed in a wrestler. He was a mat genius, had inhuman cardio, but most importantly, he was consistently one of the greatest personalities on the roster.

Who else could seamlessly transition from colossal dork to the wrestling machine with perfect consistency? Who else could win a gold medal for America and still generate huge heel heat every single week with his amazing ‘Three Is’ promos. There are many examples in the attitude era of Kurt shelving his ego and debasing himself for the greater comedic good, whether it be mocking the Undertaker on a tiny scooter, wearing the tiny cowboy hat, or dressing up like a mini-me version of ‘Taker.

But actually, his greatest crowning moment in the attitude era was a rare moment of Kurt being the dominant babyface as he crashed Steve Austin Appreciation night the Raw after SummerSlam 2001 and soaked the entire Alliance with milk. Tony would have been proud. It succeeds both as a hilarious parody of Austin’s beer bath whilst also being uniquely cool in its strange nerdy badassery, which is pretty much Kurt Angle’s career right there. Bonus points to JR for the line ‘the billion dollar princess has become a dairy queen’ and a special guest appearance of Shawn Stasiak running into a thing.


3. Heel Austin (2001)

https://www.youtube.com/watch?v=jIOMEymyLnY

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Taken as a whole, when you consider its potential, the Invasion of the WWF by the Alliance was a lot of things. Bad, crap, s***, but it actually had some great stuff nestled in amongst the money pouring through WWE’s fingers.

Milkomania was one, but greater even than that was Steve Austin’s run as a bizarrely affectionate heel. After turning at Mania X-7, Austin went from being the biggest badass on the planet to a colossal McMahonophiliac as even his own mind couldn’t comprehend the turn and melted in the sun. Austin began telling Vince he loved him, serenading him with Kum By Yah, and best of all, while Vince was trying to rally the troops before invasion, repeating the last word Vince said whilst puffing out his chest like he was a superhero .

Stone Cold Steve Austin trying to look tough is odd to seem, but absolutely hilarious and everyone who shared a promo with him got to shine. Even legendarily bad promo Debra got some laughs when onscreen with Heel Austin. One great promo saw her get soaked in milk. “You look ridiculous” said Austin, before shouting “I’m the champion” to which Debra responds “I’M DEBRA”.

2. Pretty Much Everything Team ECK Did

https://www.youtube.com/watch?v=WHPW52LuD_0

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Team ECK were Edge, Christian and Kurt Angle, and they were the funniest thing going in 2000. If dunking on the hometown crowd’s local sports franchise was an Olympic sport all three of them would be gold medallists and there are so many highlights of them as a team.

Christian playing Triple H’s theme on a kazoo while Edge screams “IT’S MY TIME” over and over, the five second pose of Kentucky’s greatest cultural achievement, “the jug band”, the period of time when Edge and Christian pretended to be Los Conquistadors by dressing in Film Academy Gimpsuits, dressing in Elvis fatsuits, Edge turning to Christian in the locker room saying “you know the best thing about my boots? It says Edge on them,” to which christian responds “that’s pretty cool I’ve never noticed that before”.

They also proved to be the perfect goofball foils to Commissioner Foley, because as has been made clear, Mick Foley makes everything better with his cuddly presence, including a great PPV long angle at No Mercy of Edge and Christian trying to get out of defending their tag titles by faking food poisoning. There was a worry about them having “bad nuts” but fear not “their nuts rule all”. Stupid. Great. Stupid.


1. This Is Your Life (Raw – September 27, 1999)

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God bless Mick Foley, king of nice. The Rock n Sock connection are the greatest odd couple in WWE history, two stars with unique charisma, bouncing off each other perfectly. You could describe their dynamic in a number of ways – Incredibly confident dad and his weird son, Versace male escort and his weird son, high school jock and high school murderer.

The peak of their brilliance was, of course, the This Is Your Life segment where Foley tried to celebrate the Rock’s birthday by bringing out people from his past, like his home economics teacher, his old coach and his high school sweetheart. Despite the segment lasting approximately 80 mins it’s carried by Rock’s brilliant no-selling of the festivities, cussing out all the guests for past slights, including scrubbing rock from the team, cutting him off at second base and, worst of all, not letting him make pancakes.

Watching the rock tell an older woman to check her ‘Aunt Jemima no pancake having ass into the Smackdown hotel’ is an important memory. It’s amazing, with the perfect punchline being that The Rock’s birthday is ‘May 2nd you dumb son of a bitch’. After being mistreated by the rock for the entirety of their partnership, Foley got the last laugh months later with a secret bonus moment.


Number 0. Foley Foley Foley (Raw – July 3, 2000)

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This is the funniest moment of the attitude era and I don’t care if you disagree. July 2000 and Foley had just been made Commissioner Foley, absolutely the best version of Mick Foley.

No career shortening bumps, just cheap pops and constant hilarious segments, peaking with this. One week into his tenure, the Rock welcomes Foley back to the WWF who asks Rock how it feels to be WWF Champion once again. As he answers, Foley screams “IT DOESN’T MATTER HOW IT MAKES YOU FEEL” as the crowd erupts.

Then, because he is the purest distillation of a likeable man, Foley then gives himself a victory lap, running around the ring chanting his own name as the rock just stands there grinning, ‘yup, you got me’.

Perfect.

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