As much as WWE fans tend to romanticize the Attitude Era, it has to be noted that a lot of it wasn't as good as remembered. Much of that era wouldn't fly in today's world, especially the treatment of women and some bad gimmicks. There's also the sad fact that it went too far trying to present "edgy" wrestling with less-than-spectacular results.
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For every absolute classic match of this time, there was another that lands itself on lists of the dumbest ideas wrestling has ever seen. Astonishingly, several of these had some top stars involved who somehow got themselves into a match that wouldn't pass muster today. Some matches may have sounded great on paper and faltered in execution, while others were stupid from the get-go. With a lot of candidates, these are 10 of the most ridiculous matches of the Attitude Era as a reminder not everything was golden at this time.
10 Iron Circle
Ken Shamrock and Steve Blackman were two top-notch fighters who could make a great brawl work. This was not a good way to do it. Rather than a ring or even an octagon, the pair faced off in a parking lot surrounded by cars with various weapons. Like many "outdoor matches," the lighting was awful and made it hard to see the action.
There was also how the setting served no real purpose with the idea that whoever got out of the circle could win, but then Shamrock was declared the winner, choking Blackman out with a chain. It was another concept too much for a simple bout.
9 The Dungeon Match
For years, the legends had grown of Stu Hart's Dungeon, where he trained wrestlers in a cramped room with a regiment that would make Marines wince. Having an actual match held there sounded good, but it didn't quite work as planned as Owen Hart faced Ken Shamrock for a pre-taped match at Fully Loaded 1998.
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It was two grown men fighting in a cramped basement room that didn't offer much for serious action. That included Owen managing to smash Shamrock's head upward into the ceiling. Owen hit Shamrock with a barbell for a submission win in less than five minutes for a match that needed a larger space to work.
8 Dog Poop
WWE really had a thing for making dog-themed matches for Davey Boy Smith. It was one thing for a bout involving eating dog food, but they went the extra mile for No Mercy 1999. The Bulldog and Rock faced off in a match where the only way to win was to slam your opponent in a massive pile of dog droppings right in the middle of the ring.
It's as disgusting as it sounds with various close calls by both guys while the announcers talked of how much the ring stank. The Rock finally Rock Bottomed Davey Both into the pile to end a bout that truly stunk from start to finish.
7 Striptease Match
While the ladies of WWE could be great in this time, they often had to put up with some demeaning matches. This was one of the worst as in In Your House: Rock Bottom, Jeff Jarrett faced Goldust in a "striptease match." This meant that if Goldust won, Debra would have to do a striptease, while if Jarrett won, Goldust would strip.
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The match wasn't too awful but hampered by that strip stipulation. Shawn Michaels somehow interfered to let Goldust win only for Debra's striptease to be interrupted by the Blue Blazer. A bad match marred two good wrestlers.
6 Halftime Heat
Long before 2020 made them a necessity, "empty arena" matches were used now and then. Having it air during the halftime of the 1999 Super Bowl sounded fun and The Rock and Mankind was ready to go at it.
But the "match" was an overly choreographed affair, and the empty arena lacked the spark needed to make it a big deal. The ending was goofy with Mankind using a forklift to lower a pallet on The Rock, who lay helpless, moaning for help rather than moving. It's not exactly a shining moment in the Rock/Mankind feud.
5 Hardcore Evening Gown
In terms of downright painful matches of the Attitude Era, it's hard to top this. Former friends Pat Patterson and Gerald Brisco were feuding over the Hardcore Title and the decision was made to have them fight in a Hardcore match...in evening gowns.
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Yes, two men in their 50s and long past their prime dressed in drag and fighting with weapons. Jim Ross and Jerry Lawler openly apologized to the audience for having to watch it. To the joy of everyone, Crash Holly raced in to win the belt himself and put this atrocity to bed.
4 Dumpster Trash
On paper, Mick Foley and Terry Funk in a hardcore tag team match should have been terrific. But WWE marred it with the pair facing The New Age Outlaws in a Dumpster match at WrestleMania XIV.
The rules were simply whoever tossed their opponents into a dumpster won. It was a messy fight that ended with the hardcore icons winning the belts by tossing the Outlaws into the trash. The Outlaws regained the belts the next night while joining DX. Amazingly, WWE revived this gimmick for Braun Strowman despite being one of the goofier stipulation matches of this era.
3 Too Much Vs Al Snow & Head
Al Snow was never known for playing with a full deck, but this was nuts even for him. At King of the Ring 1998, Snow faced Too Much (later known as Too Cool) with his partner being...Head, as in the mannequin head he would bring to the ring. Yes, Snow would have Head balanced on the ring corner and occasionally go over to ask for "advice" while Brian Christopher and Scotty 2 Hotty just stared at each other.
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Oh, and Jerry Lawler was the guest referee, clearly not believing this was happening. It ended with Christopher pinning Head with a shampoo bottle for the "Shoulders" part. Even as a comedy match, this was bizarre.
2 Tables And Dumpsters
Imagine the WWE brain trust in 2000. "Okay, so the Dumpster match was bad. But folks love table matches, so combine those, and we have a winner!" Sure enough, at King of the Ring 2000, The Dudley Boyz took on Road Dogg, X-Pac, and Tori in a Dumpster Table match.
Unfortunately, the tables had little purpose other than knocking guys into them while Tori just hid in the Dumpster. Finally, DX was able to get the Dudleys into the dumpster to win. Afterward, the Dudleys put Tori through a table to end a bad mix of matches.
1 Kennel From Hell
No list of the most ludicrous Attitude Era matches would be complete without this. Someone thought a Hell in the Cell with actual dogs for a match between Big Bossman and Al Snow sounded funny. But it was too late before they realized dogs are harder to control in a situation like this. The dogs would run around with one defecating right at ringside to make it a ridiculous sight. Even if the match had been a five-star affair, it wouldn't make up for how stupid this gimmick was and idiotic to watch.
