For the modern wrestling fan, the Attitude Era is fondly looked backed at as the greatest time in wrestling history. They had the greatest Superstars, the greatest storylines, and the greatest audiences of all time while the WWE was riding the biggest wave of momentum they ever had, or will ever have. Nostalgia has a funny way of making us look at the past with rose colored glasses as we're about to see when taking a look back at the darkest moments to come from the "greatest" time in wrestling history.
Between some of the most insane stories you could ever imagine and some of the worst wrestlers being employed in WWE history, there was no shortage of really awful moments to chose from. Even though The Attitude Era was rather short-lived, it did manage to produce some of the greatest moments in wrestling, as well as more than it's fair share of the worst.
20 Rikishi Does It For The Rock
The WWE found themselves in position yet again to create a new main event Superstar when Steve Austin had to be written off television so he could undergo neck surgery, leading to him getting hit by a car in the parking lot before Survivor Series in 1999. The biggest star of the era was going to be out for a considerable amount of time and whoever was responsible for the attack would surely be launched into the stratosphere, competing in his spot for titles right?
Well things didn't work out quite like that when the WWE decided that perennial mid carder, the dance machine, Rikishi would be tabbed as the one behind the wheel. Any possible chance that they had of making Rikishi the next big bad main event heel was ruined pretty much immediately when he admitted that his biggest motivating factor in the attack wasn't because he had a major change in attitude and was determined to do whatever it took to make it to the top. No, instead he "did it for The Rock."
It didn't take long for the WWE to realize the mistake they made and they quickly pushed the responsibility, and heat, for the attack from the big Samoan to Triple H instead.
19 Austin Nearly Gets Embalmed
It's really amazing that The Undertaker has been wrestling as long as he has, not so much because of the difficulty of being in such a physically demanding profession for 25 years, but because he should've been arrested for attempted murder on more than one occasion.
One example came during a Monday Night Raw segment with Steve Austin where The Rattlesnake was smothered by Taker backstage then dragged away to his famous hearse. The original plan was to simply bury Austin alive, but Steve woke up at the grave site and began fighting back until Taker was able to subdue him once again and decided that burying wasn't enough. Taker and Bearer ended up taking Austin to a local mortuary with the intent of embalming him alive and even got as far as having him set up on the coroner's table, shirt open, with a knife above his chest ready for the incision until Kane somehow showed up to stop The Deadman.
18 Mideon Gets Initiated
By the time 1999 rolled around, it was time for The Undertaker to reinvent himself, which is something he's had quite the knack for doing over the years as we'd find out. Re-emerging onto our TVs, The Undertaker appeared as a demonic cult leader looking to spread the power of darkness and take over the WWE.
There's no better way to get that idea over than with a bit of good old fashioned human sacrifice, as Dennis Knight found out the hard way. After being tortured by what turned out to be The Ministry of Darkness, Knight was brought out onto the stage seemingly unconscious while The Undertaker made his dramatic re-debut, telling the world about his plans to spread darkness. Knight was re named Mideon by Taker and forced to drink The Deadman's blood before having the symbol of The Undertaker etched into his chest with a dagger while Taker was speaking in ancient tongues.
17 Brawl For All
During The Attitude Era, the WWE was about one thing above anything else, realism. They wanted what was happening on screen to seem like it wasn't coming from a team of writers in the back and that the performers on screen weren't just following a script. They thought the best way to accomplish that was to stray away from their norm and actually make it real. So they came up with the bright idea to have a real life boxing/MMA tournament called Brawl for All. The main purpose of this tournament was to push "Dr. Death" Steve Williams to the top of the card by having him look like a legit bad ass, but there was one big problem with that plan; this wasn't scripted.
Williams was KO'd in the second round, destroying all the plans that the WWE had for the event, making them scramble for a new big finish, so they decided to bring in Butterbean to face off against the winner of the tournament, Bart Gunn, at WrestleMania XV. Things went about as well as you would expect from a wrestler taking on a world famous boxer in a straight boxing match with Bart Gunn embarrassing the whole company, keeping the image of wrestlers just being fake fighters who can't actually hold their own alive and well.
16 The Undertaker Hangs Big Boss Man
During the early stages of The Undertaker's WrestleMania streak, there were more than a fair share of duds, including his match against The Big Boss Man which took place within the confines of Hell In A Cell.
Obviously Taker went on to win the contes,t but it's what happened after the match that had people talking the next day, as with the help of The Brood, Boss Man was hung from the top of the cell as it ascended back up to the rafters. The poor Boss Man just couldn't catch a break back in The Attitude Era, as we'll talk about a little later, but this was certainly an example of things going a little too far in the wrestling ring. While we're fine with watching people punch each other in the face or hit each other with steel chairs, seeing someone get lynched right in the middle of the ring was a touch too much for most.
15 Vince Is The Higher Power
One of the biggest storylines that ran through The Attitude Era involved finding the identity of the mystery man that was pulling The Undertaker's strings, forcing The Ministry to do heinous things like kidnap Stephanie McMahon and force her to marry The Deadman. Luckily for her, Steve Austin was there to keep The Ministry at bay which led to one of the most underwhelming reveals in WWE history, as the Higher Power that was behind The Undertaker was none other than Vince McMahon himself.
The man behind the plans to torture the McMahon family and make life as difficult as possible for everyone unlucky to cross their paths was the patriarch of the McMahons...he really must have hated Steve Austin to put his family through all of that I guess.
Instead of using the golden opportunity that was sitting right in their laps to create a new star, the WWE went with the laziest route possible, choosing instead to reignite the McMahon/Austin feud that had really run it's course by that point.
14 The Artist Formerly Known As Goldust
Ever since his debut, the whole point of the Goldust gimmick was to test the boundaries of the audience and make them question exactly what it was they were watching. Immediately upon his debut, he was achieving that goal, pushing the limit of what the audience was comfortable watching week after week, but things got pushed even further during The Attitude Era.
After splitting paths with his wife Terri, Goldust found himself a valet that could match him in terms of strangeness, hooking up with Luna Vachon. This is when Goldust went in an entirely new direction and started being referred to as The Artist Formerly Known As Goldust, ditching the trademark gold outfit and facepaint for something a little more abstract. He began wearing more dominatrix like outfits in a wide variety of vomit inducing colors, along with the occasional bra and ball gag. He was truly a sight to behold, you just couldn't keep your eyes on it for too long.
13 Meat and PMS
This entry could have just been about PMS, the trio of Jacqueline, Terri Runnels, and Ryan Shamrock, as it didn't take long for the trio to live up to that awful name while messing with D-Lo Brown, but that's something we'll get into more detail about a little later.
While what they did to D-Lo was pretty awful, what they did to Shawn Stasiak was just as bad and this was back when he was known as Meat. Stasiak was used as a boy toy for the group, who quickly turned into a jobber after starting his run with an undefeated streak because he started getting too tired from making love to the trio before his matches. All that led to the classic comedy act of slipping an unknowing participant a certain pill to help with erectile dysfunction, causing Stasiak to try and work a match with an "erection." Comedic gold.
12 Mark Henry And The Transvestite
Poor Mark Henry never caught a break in the love department throughout The Attitude Era, despite being billed as 'Sexual Chocolate.' Henry found himself infatuated with the ninth wonder of the world Chyna and was desperate to do whatever it took to impress the mastodon of a women.
Henry kept chipping away at Chyna until she finally relented and proposed a wild idea to Sexual Chocolate, involving her good friend Sammy. Henry and his new friend Sammy got along rather famously and even found themselves alone in a hotel room one night where things were starting to get a little hot and heavy. While getting a little bit handsy with his new buddy, Henry felt something below the belt that didn't belong there and proceeded to freak out, vomiting right then and there.
11 Evening Gown Match Between Legends
The booking team back in The Attitude Era sure did love themselves gimmick matches. Some were good, some were bad and some were just downright ridiculous, such as this one. Not only were Pat Patterson and Gerald Brisco far too old to be stepping in the ring at all, they were doing so over a title. To be fair it was the Hardcore Title, which had become a bit of a joke by that point, but that's beside the point.
Not only were they facing off for a championship, but they did so in perhaps the most ridiculous gimmick match of all time, an evening gown match. While everyone back then loved a good ol' bra and panties match between two incredibly attractive Divas, the WWE decided to use a similar gimmick with two grandpas in a match where the winner would be the first to forcibly remove the other's evening gown. We saw two legit legends of the business being degraded to nothing but a wildly silly sideshow, which goes down as an embarrassment to everyone involved.
10 The Rock Nearly Kills Mankind With Chair Shots
In a moment made infamous thanks to the terrific behind the scenes documentary Beyond The Mat, the full damage a steel chair can do was on display during this I Quit match between The Rock and Mankind.
Wrestlers aren't even allowed to hit each other in the head with steel chairs anymore, mainly thanks to this match.
Obviously we know more about the damage multiple shots to the head can do today than we did back in the late 90s, but that doesn't make it any easier to watch, as Mankind took chair shot after chair shot to his unprotected head. It was a moment so brutal that you could almost feel the shots yourself through the screen as The Rock continued to pummel Mankind's head, leaving his scalp cut wide open after the assault.
9 Beaver Cleavage/Chaz
The man formerly known as Headbanger Mosh found a modicum of success in the WWE. winning the Tag Titles before his utter disaster of a re-branding. In The Attitude Era, the most successful stars didn't do anything too complicated, as they pretty much just played themselves turned up to 11.
The WWE tried to do the complete opposite of that with Chaz who was having vignettes aired about his return under the new ring name, Beaver Cleavage, which is indeed a play off of a TV show from 40 years earlier. The incredibly awkward vignettes tended to hint at the idea of Beaver being sexually attracted to his own mother, but thankfully these didn't go on too long, as just a week after his debut, Beaver spoke out against the insane gimmick and rechristened himself Chaz, with the woman playing his mother actually being his girlfriend.
That seems like a step in the right direction until WWE started playing up the angle of Chaz being a women beater and getting incredible heat from the other wrestlers for it. Going from a man lusting after his own mother to an alleged women beater surprisingly isn't the way become a main eventer.
8 Big Boss Man Crashes A Funeral
It seems that during The Attitude Era, any wild and crazy storyline that the writers could come up with would end up on TV, usually being carried out by The Big Boss Man. We already covered one incident and there's another on the way, but for now we'll talk about the time he got a little carried away during the funeral for Big Show's father, or more accurately Show's dad got carried away.
The camera came in on Big Show saying a few words over his dad's coffin while friends and family somberly watched on, until Boss Man came in, driving an old fashioned cop car with a comically large speaker attached to the top, spouting insults at every member of Big Show's family, including asking Big Show's mom if she'd go out with him now that she's single.
Obviously Show didn't take too kindly to this and tried to attack Boss Man, but it was all part of the plan, as after Show was knocked to the ground, Boss Man chained the coffin to the bumper of his car, while saying that Big Show's dad always wanted to be a drag queen, so he was going to make that wish come true by dragging the coffin around the cemetery. Big Show made one last ditch effort by jumping onto the runaway coffin as Boss Man drove away.
7 Birth Of A Hand
There isn't much doubting that this was one of the most iconic moments of The Attitude Era, something that has been permanently scarred into the minds of anyone unfortunate enough to have seen the event live.
The whole angle was pretty horrifying from the beginning. With someone the size of Mark Henry dating someone the age of Mae Young, you knew it wasn't going to end well for the pair. When Mae Young announced that she was pregnant, we knew something foul was going to come from it, but no one had any idea of what was about to come.
During a match that pitted Mark Henry against Crash Holly, Young delivered a splash before doubling over due to what appeared to be stomach pain. Once backstage and surrounded my medical personnel, it was revealed that it was time for Mae to deliver the child, but as the whole audience watched in disgust, we found out it wasn't a whole human in there, it was just a prosthetic hand.
6 Choppy Choppy Pee Pee
Perhaps the most infamous quote from the entire history of the WWE, "I choppy choppy your pee pee!" is truly something that could have only ever came from The Attitude Era. In classic late 1990s fashion, the feud between "adult star" Val Venis and overtly racist Japanese group Kaientai began when Venis made a new film starring the wife of the group's manager, Mrs. Yamaguchi.
When that news came out, Mrs. Yamagichi's husband was furious, threatening to take his frustrations out on his wife until Venis made the save. That was when the Japanese leader truly had enough, demonstrating his next plan of attack using a samurai sword and a salami, screaming at Venis that he was going to "Choppy choppy your pee pee!" The threat nearly came true too as the group had Venis tied up in the back mere seconds away from being able to deliver the castrating blow until the lights went out thanks to none other than John Wayne Bobbitt... who actually had his part cut off by his wife in real life.
5 Al Snow, Big Boss Man and Pepper
Poor Pepper, that little dog sure had a tough life in the WWE starting off with having the misfortune of being paired with Al Snow as a way to help silence the voices in his head. Things only got worse when Snow started feuding with The Big Boss Man.
Boss Man was so desperate to get a shot at the Hardcore Title that he kidnapped Pepper from Snow to threaten the puppy until Al granted him a shot at the title. Snow relented and gave Boss Man the title shot he so desperately wanted, but the former prison guard wasn't about to give up his leverage that easily, as he left the ring following their match with the dog still in his possession.
It seemed as if Boss Man was finally having a bit of a change of heart, as he offered Snow his dog back if he'd meet him at his hotel room. When Snow got there, the dog was nowhere to be found, which Boss Man blew off by saying Pepper was at the groomer, while Snow was offered a plate of beef and noodles. After Snow took a few bites, Boss Man revealed that Al Snow had just eaten his own puppy. The worst part of it all was still to come though, as they had an infamous Kennel From Hell match, which was the way they chose to end this feud.
4 Terri's Fake Miscarriage
We talked briefly about the PMS group and their diabolical plan to get D-Lo Brown on their side a little bit earlier, but now is the time to dig into how truly awful this story was. It all started with Terri Runnels managing and being in a relationship with Val Venis, who ended up getting her pregnant. When Val heard the news, he dumped her on the spot, leaving Terri struggling to find someone new to fill the void in her life.
While trying to win the favor of D'Lo Brown, for some reason, she got knocked off the ring apron by Brown, leading to a miscarriage for Ms. Runnels. Brown felt so bad that he started working with Terri and Jaqueline who were blackmailing D'Lo into doing all of their dirty work. This would continue until, in a classic Vince Russo twist, he found out that Terri was never pregnant, leading to a hostile split between the two. Wow.
3 Mae Young Flashes The Crowd
There are very few things that fans in the late 90s loved more than puppies. It was a huge marketing point for the company and pretty much the only thing that came out of Jerry Lawler's mouth as he boyishly ogled the women well beyond the point of making everyone listening feel uncomfortable. The only thing more unanimous among the WWE faithful than their love of puppies was their disdain over Mae Young's.
Back at the Royal Rumble in 2000, there was a Ms. Royal Rumble bikini contest, because that's a thing they loved to do back in the day, which was originally supposed to be contested by Ivory, Jacqueline, The Kat, Luna Vachon, and Terri Runnels until the last minute addition of Mae Young to the contest.
Young certainly had the most conservative of the swimsuits, rocking an old lady one-piece suit, but she didn't keep herself covered for long, as she would whip out her puppies in an attempt to impress the judges. Somehow, that was enough to win the contest over her much younger, and more attractive, competition and Mae Young became the first, and only, Ms. Royal Rumble.
2 Hawk Falls Off Titantron
It seems so obvious now, but even back in the late nineties, bringing The Road Warriors back into the fold couldn't have been considered a good idea. Ever since their initial run with the company roughly six years earlier, the pair deteriorated slowly, more so Hawk than Animal, into a world consumed by nothing, but drugs and alcohol.
Classic Attitude Era WWE decided that realism was more important than anything else and began incorporating the personal struggles of Hawk into storylines, having him "portray" an alcoholic who wasn't able to compete in the ring anymore. Animal found a new partner in Droz, which had less than a zero percent chance of succeeding in the first place, and they found themselves involved in one of the most ludicrous moments in wrestling history.
Eventually, Hawk had enough of being pushed aside by his former friend and climbed to the top of the titantron, threatening to jump and kill himself, only for Animal's new partner to follow him to the top, attempting to reason with the man. As if that wasn't insane enough, it ended with Droz casually pushing Hawk off the top and a silhouette being shown behind the screen of Hawk's body falling to the floor.
1 Trish Forced To Bark Like a Dog
Nothing defines the glorified era quite like Vince McMahon degrading women and inflating his own ego, and in this instance we get classic examples of both! Early in her WWE career, Trish Stratus wasn't seen as a wrestler, as she was just arm candy for whoever the flavor of the month was to try and garner some interest. It didn't take long for Trish to find herself paired up with Vince McMahon, but let's face it, if you were in charge, you'd book the exact same thing.
Trish started showing signs of wanted to break free of the oppressive relationship, but when her first attempt failed, Vince wanted to make an example out of the future Hall of Famer. Vince forced Trish to make an absolute fool of herself, ordering her to get on her hands and knees, screaming ""Now then, I want you to tell me in dog language just how sorry you are! Okay? Yeah, tell me in dog language! Speak, Trish, speak! YEAH, BARK LIKE A DOG!""
If that wasn't horrifying enough, he followed that with orders for Stratus to strip while apologizing to him in one of the most disgusting segments of all time.
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