Back in the 1980s, the WWE was known for having very safe and tame matches. It was the classic good guy versus bad guy stories that got kids hooked into it, and many still watch it today. As those kids grew up, though, they wanted to see something a little edgier, and that’s where the Attitude Era came into play.
That era gave us some of the strangest and most brutal matches of all time in the WWE, giving us offensive storylines that probably wouldn’t swing today. A lot of the matches got scaled back in terms of violence once the PG Era came around, but the late 1990s and early 2000s gave us a lot of disturbing matchups that probably shouldn’t have happened.
These are the kind of matches that you either felt uncomfortable watching it from the get-go. There are some matches that may have been fun for you to watch as it was unfolding, but looking back on it now, they might make you squirm.
You won’t see too many recent matches on this list, with only one coming after the year 2005. You also won’t see any matches older than 1998, because that’s when it seems that the matches really got ramped up into a Rated R setting. Between intergender beat downs, extreme blood loss and lack of general safety, there were a lot of disturbing matches in the era.
Which ones stand out as the most disturbing of all time, though? Here are the 20 matches that had you looking away from the screen out of horror or disapproval.
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20 John Cena vs. Brock Lesnar - Extreme Rules 2012
Brock Lesnar departed from the WWE after Wrestlemania XX and didn’t get back into a WWE ring for a match for another eight years when he came back to fight John Cena. After spending time in the UFC, it was clear that Lesnar was having trouble pulling his punches. Lesnar has a reputation for making things look just a bit too real, and this was one of those cases. Cena took a quick beating and busted open his forehead that kept opening up throughout the match. Lesnar also took a chain wrapped fist to the face, perhaps overselling it. Still, it was good to see Lesnar back in a WWE ring.
19 Undertaker vs. Vince McMahon - Survivor Series 2003
Vince McMahon was already a heel throughout the Attitude Era, but he ramped it up big time in 2003. After taking on seemingly all of the Smackdown roster, Vince McMahon turned his sights onto The Undertaker by costing him a match against Brock Lesnar the month before. At the Survivor Series pay per view, the two went head to head in a Buried Alive match. Undertaker split McMahon’s forehead open almost immediately into the match. The boss was bleeding all over the place for the entire match, which he ended up winning after interference from Kane.
18 Pat Patterson vs. Gerald Brisco - King of the Ring 2000
Pat Patterson and Gerald Brisco were the hired stooges for the authority of sorts back in the Attitude Era, and were subject to humiliation when they crossed the boss. For some strange reason, the two were forced to square off for the Hardcore Championship at King of the Ring in 2000. That sounds alright, but they were forced to wear evening gowns while doing it, along with full makeup. What made it even worse is that it’s likely that some of the higher ups at the WWE knew that Pat Patterson was gay and probably took humor in it.
17 Al Snow vs. Big Boss Man - Unforgiven 1999
There are a lot of things that make this awful match a disturbing one. The most disturbing part was the storyline where Big Boss Man served Al Snow a dinner, only to reveal that he was eating his dog, Pepper. The two decided to take out their frustrations on each other in a Kennel From Hell match that featured large dogs relieving themselves on the arena floor. Seeing dogs chained up in front of a large crowd like that and freaking out was a pretty disturbing sight that upset some animal rights activists.
16 Edge vs. Mick Foley - WrestleMania 22
If you’re a fan of hardcore matches, then this one between Edge and Mick Foley at WrestleMania 22 was an instant classic. If you get a little queasy by seeing blood and violence, then this match was awfully disturbing. The feud was a memorable one that started when Foley was the referee in a match that Edge lost, so the two settled the score on the biggest stage. By the end of the match, Edge had lost a tremendous amount of blood and did a good job of making it look like he was going into shock after spearing Mick Foley through a flaming table.
15 Undertaker vs. Big Boss Man - Wrestlemania XV
During the early parts of 1999, the Undertaker was the leader of the Ministry, a dark stable that took multiple ‘sacrifices’ that almost nobody was safe from. That included the Big Boss Man during their Hell in a Cell match at Wrestlemania XV when The Brood descended to the top of the cell and dropped a noose down to The Undertaker. The Deadman then went on to literally hang the Big Boss Man in the middle of the ring while people looked on in horror during the biggest event of the year.
14 Brock Lesnar vs. Undertaker - No Mercy 2002
The Undertaker and Brock Lesnar made a lot of history with each other during the early portions of Brock Lesnar’s career. The two went head to head inside of a cell during the 2002 No Mercy pay per view that saw a lot of blood being lost in the ring (and even outside of the cell). All of the members involved ended up getting bloodied, even Paul Heyman. Lesnar even slammed a chair into Undertaker’s arm cast multiple times that made people wince. Lesnar would end up winning after giving Undertaker the F5 onto a blood-soaked mat.
13 John Cena vs. JBL - Judgment Day 2005
JBL was the top of heel of the beginning of the Ruthless Aggression era, and perhaps he was just a little too good at it. As John Cena was elevated into the main event and took on JBL in an “I Quit” match at 2005’s Judgment Day, he got a nice welcome to the big show. JBL whipped Cena with a belt, and even choked him multiple times with it and an extension cord. By the end of the match, Cena was wearing a crimson mask, one of the worst to be seen in a WWE ring. As per usual, though, Cena was able to overcome the odds and forced JBL to quit.
12 Zach Gowen vs. Brock Lesnar - Smackdown, 2003
Zach Gowen was hired into the WWE in a pretty unique way, especially since he only had one leg. Gowen was smaller than pretty much every wrestler on the roster, and is probably even smaller than the average man. He got fed to Brock Lesnar on an episode of Smackdown by Vince McMahon in the of the most one-sided fights in WWE history. Lesnar destroyed Gowen left and right in front of his mother, even throwing Gowen’s prosthetic leg in front of her. Hearing Gowen’s mother pleading with Lesnar to stop the beatings was tough to watch.
11 Shane McMahon vs. Steve Blackman - SummerSlam 2000
Shane McMahon didn’t have much formal training, and he was the boss’s son. So to win some respect with the rest of the locker room, Shane tried a bit too hard to take some crazy bumps. In a match at SummerSlam 2000 for the Hardcore Championship, McMahon went all out with his spots. The craziest was when McMahon climbed all the way above the titantron on the ramp and leaped down what had to be at least 40 feet. For a second, people in the crowd legitimately thought they were going to see a millionaire die in person.
10 Vince McMahon vs. Hornswoggle - Raw, 2008
The WWE’s history with little people in the ring is questionable at best, and this might have been the epitome of mistreatment. Vince McMahon was in an angle with Hornswoggle that revealed that the leprechaun character was his son. JBL was doing his usual heel tactics back in 2008 and once again ended up taking it too far when he joined the steel cage. JBL handcuffed Finlay to the steel cage and forced him to watch the beating that he gave to Hornswoggle. JBL tossed him around the ring, and seeing Finlay desperate to get out of the handcuffs was a disturbing sight that not many people in the crowd reacted kindly to.
9 Stone Cold, Triple H and Stephanie McMahon vs. The Hardy Boyz and Lita - Monday Night Raw
Stone Cold Steve Austin was coming off perhaps the most memorable heel turn in history. The only problem, was that people were still cheering him, so he knew he had to get more heat. Stone Cold teamed up with the other top heel, Triple H and had a mixed tag match along with Stephanie McMahon to take on the Hardy Boyz and Lita. Stone Cold got the heat he was looking for when he started blasting Lita with a steel chair repeatedly. Lita earned a lot of respect because it was her idea, but it was still disturbing.
8 Chyna vs. Pat Patterson and Gerald Brisco - Monday Night Raw
Those that were watching this match at the time in 1998 had to do a double take when all of a sudden the screen got blurred out. During this handicap match between Chyna and the Stooges, the two men were able to get the upper hand on Chyna momentarily. Chyna held her own, so it wasn’t the men fighting women mentality that was really the disturbing part. That came when Brisco groped Chyna’s breasts on the air and then the beatdown that happened after some interference. Michael Cole and Jerry Lawler cackling like hyenas the entire time certainly didn’t help things either.
7 Triple H vs. Cactus Jack - Royal Rumble 2000
Triple H was in need of a heel push during the middle parts of the Attitude Era, and getting in a hardcore Street Fight at the Royal Rumble against one of the most lovable guys in wrestling was the way to do it. Both men took an absolute beating and got split wide open. The match was considered to be one of the best that either one has had, but there were some uncomfortable parts that included getting a Pedigree face first into thumbtacks, even sticking out of Mick Foley’s eyebrows.
6 Edge, Lita and Mick Foley vs. Tommy Dreamer, Beulah McGillicutty and Terry Funk - One Night Stand 2006
Technically this is an ECW match, but the WWE had already taken over the company at that point so their wrestlers could show up on either roster. This six person intergender tag match featured just about every disturbing aspect that you can think of. There was blood, a massive array of weapons, women taking a beating from men, you name it. The most dynamic part of the match was when Terry Funk was screaming to Mick Foley about his eye and asking for help. It was very convincing to the point where people thought his eye really got knocked out by Mick Foley.
5 Stephanie McMahon vs. Vince McMahon - No Mercy 2003
What other company in the world would proudly display the boss getting into a fight with his own daughter? That’s what happened back at No Mercy 2003, just before Stephanie was going to get married to Triple H. What made it even worse is that the match was an “I Quit” match, so you knew it was bound to be way too brutal. There are already a lot of people that call the McMahon family a bunch of carnies, and that did nothing to squash that reputation. Vince ended up winning when Linda threw in a white towel to stop the match.
4 Eddie Guerrero vs. JBL - Judgment Day 2004
At this point, you shouldn’t be too surprised to see JBL’s name on this list. The two did battle at Judgment Day in 2004 for the WWE Championship, but even the setup to the match was hard to watch. JBL cut a promo on Eddie Guerrero about how his family was filled with illegal immigrants. JBL split Eddie’s head open, and it looked like Eddie was going to pass out from blood loss at any moment. Just to make matters worse, JBL slammed him on the head with a chair after he had already lost a ton of blood on the mat.
3 Kurt Angle vs. Shane McMahon - King of the Ring 2001
Kurt Angle and Shane McMahon got into an angle together in 2001 when Shane announced that the WCW was coming back and interfered in a bunch of Angle’s matches. At the King of the Ring even, Kurt Angle defeated Christian, but lost to Edge in the finals. To take out his frustrations on Shane McMahon, the two had a nearly 30 minute Street Fight where Angle was told not to take it easy on the boss’s son. Watching Shane get thrown into the glass multiple times and watching it not break while he landed on his head had you wondering if the guy was even sane.
2 The Rock vs. Mankind - Royal Rumble 1999
When it comes to telling a good story, this match between The Rock and Mankind at the 1999 Royal Rumble did a great job. However, they did it at the expense of Mick Foley’s safety, and even did it in front of his family. While filming “Beyond the Mat”, Foley’s wife and children were sitting ringside and had to watch the patriarch of the family get his hands tied behind his back and eat chair shot after chair shot in an unprotected manner straight to the head. At least you got to hear The Rock call Mankind a “fat piece of monkey crap” during the match.
1 Mankind vs. Undertaker - King of the Ring 1998
When people talk about the match that got them into watching the WWE, this is usually one of the first ones that gets brought up. That still doesn’t mean that it wasn’t the most disturbing match of all-time. The match seemed like it was over just after starting when Mankind got tossed off the top of the cell and through the announce table. After being carried away on a stretcher, Mankind came back just to get put through the cell’s ceiling and onto a bed of thumbtacks. How Mick Foley survived that match is a complete mystery, and it really cemented him as the “Hardcore Legend”.
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