22 Strangest Wrestling Gimmick Matches

William Regal really is a good sport, from “Real Man’s Man” to Mr. McMahon’s Kiss My Ass Club, Regal has done whatever asked no matter how mad, and made the very best of it. But in 2002, when Monday Night Raw emanated from Las Vegas, and matches were decided by the Raw Roulette wheel, he found he would face Goldust in a ‘Las Vegas Showgirl Match’. Which he thought meant a showgirl would accompany him to the ring. Nope. You had to dress as a showgirl for the match. Regal has called this one of the most fun things he has ever done in his WWE career and it was great to watch, as Regal in full drag stumbled to the ring in heels (the heel in more ways than one). He played it brilliantly and even got the win when he clocked a distracted (by an interfering Lance Storm) Goldust with his trusty brass knuckles...and threw in a Rockettes kick dance for good measure! Good ol’ William!

Big Boss Man would often talk about “servin’ hard time” in his earlier years in WWE and at Summerslam 1991 The Mountie really did, in their Jailhouse Match. A match where the loser would spend 24 hours in a New York City jail cell. Of course Bossman got the win and poor old Mountie was cuffed and carted off to be finger printed and locked away! Hardly a classic, it was still goofy fun but arguably this kind of thing wouldn’t play very well nowadays.

At Fully Loaded 1998 audiences were treated to a bizarrely filmed Dungeon match between Owen Hart and Ken Shamrock, with Dan Severn serving as special guest referee. Essentially it was a match filmed at the renowned Hart Family Dungeon training facility in the basement of the Hart home, which meant no ring, just mats, pipes and wood frames. It was a short but unique encounter and while not a varied match (the setting only allowed so much) from a wrestling standpoint, as a one off oddity, this one holds up quite well and is a hard hitting battle. Despite a screwy finish, the late great Owen still looked like the warrior he was here, with his cheating win over Shamrock.

WWE is no stranger to angles that are, shall we say, in bad taste or controversial, and while the late great Eddie Guerrero and Rey Mysterio’s series of matches in 2005 were excellent, the storyline involving Rey’s son Dominick and Eddie being his biological father, was a story many were not taken with. Though it did give us the “I’m Your Papi” Eddie T-shirt, so it’s not all bad. Seriously though, Rey would fight for his son’s custody, quite literally at Summerslam 2005 in the “custody of Dominick Ladder match”. No, they didn’t hang the poor kid up there, it was a contract thankfully, though Vickie Guerrero would get involved (in a botched manner) and the angle was kind of unnecessary, as WWE already had a good plot here with Eddie being driven to madness by his inability to beat his friend Rey in the ring, which eventually he did - just not here. Sadly, this was the last fully formed Eddie feud, before his tragic passing later that year, but the quality of the matches compensated for some of the creative decisions and Eddie could make anything work. One of the best ever, Eddie is truly missed.

Razor Ramon and The 1-2-3 Kid’s rivalry saw shifts in character and Ramon played the face here (resisting the urge to say Babyface!) as he battled the 1-2-3 Kid (who later became X-Pac) in the first ever Crybaby Match at WWE (then WWF) In Your House 6. The match was standard, but the aftermath was not, as the loser would be powered, put in a nappy and given a big baby bottle. Kid took the loss and seeing him get powered and placed in a comically oversized nappy was certainly embarrassing...especially to explain to any mates/family who weren’t viewers and happened to walk in on you watching it.

In the revived Extreme Championship Wrestling (ECW) days back in the late noughties, where ECW was initially reborn before being revamped into third brand of WWE, a few stars got time to shine, the biggest of which was future mega-star CM Punk. And in early 2008, Punk and Chavo Guerrero had a bit of a rivalry going, which ended up with a Gulf of Mexico match being booked on ECW TV. The match ended when, you guessed it, the fight ventured outside and someone was thrown into the Gulf of Mexico. Punk ended up getting the win by GTS’ing Chavo into the murky waters. A bizarre and quite dangerous stipulation really but it’s not the first time WWE has incorporated the Gulf of Mexico into feuds (Rey Mysterio/Jack Swagger’s No DQ match in 2010 or Cody Rhodes tossing Damien Sandow’s Money in the Bank contract into the gulf in 2013) and in 2006 Edge had a similarly-themed experience when John Cena threw him in the Long Island Sound.

It was rather typical back in the WWE Attitude era that you would see ladies compete in softcore porn-like encounters like Bra and Panties matches, lingerie pillow fights or “matches” (read: flailing n’ gasping) contested in huge bowls of Gravy/Pudding/Mud/Egg Nog. However the evening gown match was another of those creations, only at King of the Ring 2000 there was a twist. As the WWE Hardcore Championship was contested in a “Hardcore Evening Gown” match, where ageing wrestling legends Pat Patterson and Gerald Briscoe competed in drag and battled to states of undress. Our eyes are still recovering, and the match was pretty bowling shoe ugly as commentator Jim Ross would say. In fact, he and Jerry ‘ The King’ Lawler’s bewildered commentary on this one is pretty hilarious. After all, what can you say calling something like this?

There have been a number of Hog Pen matches in WWE, few of them any good. The actual rules change depending on what rivalry this one is dusted off for. But the basis is that there is a pen of pigs, with slop, mud and you know what everywhere. People either fight in the pen itself, or have to be thrown in to lose. The first (and best) one saw Hunter Hearst Helmsley (yes, Triple H) lose to Henry O. Godwinn at In Your House 5. The last - if memory serves - was the atrocious Miss WrestleMania Crown Handicap Hog Pen match between ‘Santina’ Marella and Vickie & Chavo Guerrero at Extreme Rules 2009. This one could realistically make a comeback anytime in PG era WWE, so beware.

Yes, it’s real, back in The Rock and The British Bulldog’s brief and forgotten WWE feud in 1999 (after Bulldog’s return), WWE booked a Dog Poo match on Monday Night Raw, where the loser would be the one who was slammed into a piled high tray of dog crap, which Mankind kindly collected from the local pound. An impactful Rock Bottom saw Bulldog land back first onto the stink mountain. What a load of...

Shark Cages have often been used in wrestling as a way of containing a troublesome manager or wrestler from interfering in a match, as they are often suspended above the ring (Chris Jericho at Royal Rumble 2017, Chyna at Unforgiven 1998) but way back in 1977, Chief Jay Strongbow faced Don Kent literally in a shark cage in the middle of the ring, where the winner had to pick the lock and escape. The space was so confined any exciting action was impossible, leading to a 7-minute series of grabs in a cage. Strongbow would emerge victorious thanks to some outside interference, in a match so absurd many would think were an April Fools gag.

Before cinematic matches truly caught fire in WWE this year, early experiments were made. Arguably the pioneers were Mankind and The Undertaker’s classic Boiler Room Brawl at SummerSlam 1997 but it was Impact Wrestling’s (then TNA Impact) The Final Deletion match (between Matt and Jeff Hardy) that was the medium’s media-gaining breakout. WWE would follow with their own attempts, some of which were rather great or even better (The Wyatt Family/New Day at the Wyatt Compound or Bray Wyatt and Woken Matt Hardy’s Ultimate Deletion match in 2018) but at Payback 2017 Bray Wyatt and Randy Orton ended their feud in the “unforgettable” House of Horrors match. A weird blend of in-ring and cinematic approaches but its construction was really rather confusing. Starting as a fight at a gimmicky rundown horror house, a limo journey back to the arena would mean the final fall could take place in the ring. Utterly unfocused and messy. WWE would later nail the cinematic approach with the likes of Bray Wyatt/John Cena’s Firefly Funhouse Match and The Undertaker/AJ Styles’ Boneyard match at this year’s WrestleMania 36.

If it ain’t broke don’t fix it they say. Well during Vince Russo’s TNA (now Impact wrestling) tenure, fans would witness the reverse battle royal, which you have to applaud for its warped originality but also have to ask why?! It’s a mystery as to whose idea this actually was, as the chief writer was unconfirmed at the time, and nobody has really owned up to this one and with good reason. The match was stage one in the Fight For The Right Tournament, which ran in both 2006 and 2007. Let us make an attempt to highlight the rules. The superstars start outside the ring and battle to enter it, when half of them do so, the other half are eliminated and the match becomes a standard over the top rope battle royal, with the last one standing winning and advancing. Let’s not even get into the differing year’s tournament rules. This was an overthought mess that re-mapped out a wrestling staple that didn’t need it. The wrestlers tried their best with it but what an incomprehensible faff.

Then Commissioner William Regal, and his battles with the rebellious Chris Jericho in early 2001, was a fun little rivalry, one that often goes overlooked in history. Their matches at Wrestlemania 17 and Insurrextion 2001 are fabulous (the latter especially) but at Backlash 2001 “the goodwill ambassador” Regal would get one over on his fan-favourite rival in the bonkers Duchess of Queensbury Rules match. Basically, this involved a lady dressed in a ridiculous wig and dress, claiming to be the “Duchess of Queensbury”, changing the rules in Regal’s favour as the match went along (adding time limits, no DQ’s and whatnot to help Regal out). As silly as it was, it was rather enjoyable, and Regal/Jericho rocked their respective roles beautifully.

Taking the lead from Mad Max 2: The Road Warrior (on a budget), WCW at Uncensored 1995 booked the King of the Road match between Dustin Rhodes (best known as Goldust) and The Blacktop Bully. Taking place on the back of a 18-wheeler truck, as it was driven around the roads, the combat area was confined with cage walls and padded with hay bales, and the objective of the match was to make your way to the front of the truck and climb to the top of the trailer’s cage and sound the horn. An incredibly interesting idea but one nigh on impossible to perform in, as the moving truck meant both men stumbled and struggled to stay on their feet. Aside from some guerrilla-style wall cams, the action was shot far from above with a helicopter or from an accompanying pick up truck. Bully would eventually get the win in this memorably mad match.

Never before, never again. The WWE Hardcore Championship rivalry between Al Snow and The Big Boss Man back in 1999 was at the height of Boss Man being the ultimate onscreen baddie (with the Big Show’s dad’s funeral debacle following only a month or two later). Their feud revolved around Al’s new little mascot dog (who replaced his original mascot, Head) Pepper, who Bossman kidnapped and eventually “killed, cooked and fed” to Snow in a highly controversial storyline. The finale came in the infamous Kennel From Hell Match at Unforgiven 1999. And boy were they unforgiven. The concept saw Snow/Bossman compete in both a standard steel cage and Hell in a Cell structures, and patrolling the outside of the first cage were trained Rottweiler attack dogs. In concept, this sounded deadly, in execution, it was a snooze fest brawl that has to be seen to be believed. The dogs were more taken on with each other than the wrestlers (who can blame ‘em), as puddles were made, dog trainers fell face first, and canine horniness ran wild. This one lives on in infamy and Mick Foley would even include it on his Hard Knocks, Cheap Pops DVD as an extra, with his hilarious own commentary on it, in the ultimate rib on his pal Al. Don’t expect the dogs to be let back out again folks.

When it comes to wrestling, we’ve had everything on a pole matches. Mistletoe, Fuzzy Dice, Pink slips, paddles, piñatas, leather jackets, you name it! Some have worked (Edge and William Regal’s underrated Brass Knuckles on a Pole match at WWE No Way Out 2002), others have bombed hard (The Sandman vs. Carlito in a Singapore cane on a pole match at WWE The Great American Bash 2007) and some have just been ridiculous (Buff Bagwell vs. Chris Kanyon in the infamous Judy Bagwell on a Pole - well, forklift - match at WCW New Blood Rising 2000). Well, when Vince Russo took over at WCW, ‘On a Pole’ matches went crazy. We all remember the baffling San Francisco 49ers Match with Booker T and Jeff Jarrett yeah? Well, the gimmick scraped barrel bottom when Billy Kidman took on Shane Douglas in a Viagra on a Pole match, as part of their rivalry revolving around Torrie Wilson! Ironically this one was a limp affair, and a reminder that anything - and we mean anything - can happen in wrestling...and not always in a good way.

What a doozy of a night Halloween Havoc 1995 was, as Hulk Hogan took on The Giant (aka The Big Show) in a Sumo Monster Truck match. Which saw both guys tussle behind the wheel of huge monster trucks and have to push each other out of the circle on the roof of the building (well, a nearby building) and then have an in-ring title match soon after. The truck portion of the bout went as expected, and after charging each other for 5 minutes, Hulk pushed Giant’s truck out the circle, the two then got in a heated exchange on the rooftop and Hogan accidentally knocked The Giant off the building into the dark waters below. A shocked commentary team was left wondering how the two would compete in their scheduled in-ring match only minutes later. Well, quite easily as it would happen, as - after a Randy Savage vs. Lex Luger match - Hogan came to the ring to explain the situation, and a very un-wet The Giant arrived to fight for the WCW Championship. Very believable stuff this isn’t it? The two then had a nondescript title contest, which ended in a DQ, with all manner of manager betrayal and shenanigans, and Hogan being group bear hugged (or dry humped, you decide?) by The Giant and an interfering The Yeti (Ron Reis) (a bandage covered 7’ 1” wrestler) after the match. God, what a sport this is!

People are split on WCW’s Chamber of Horrors match at Halloween Havoc 1991. This match is wrestling at its most anarchic but there is fun to be had with its horror-inspired so-bad-its-hilarious results! Abdullah The Butcher, Cactus Jack, Big Van Vader and The Diamond Studd faced the team of El Gigante (better known as WWE’s Giant González), Sting and Rick & Scott Steiner, inside a huge haphazard-looking Hell in a Cell sized cage. The aim was to await the lowering of “the chair of torture” (a big ridiculous flimsy electric chair housed in a mini-cage which took up huge space in the middle of the ring) and strap in a member of the opposing team and switch the fake-looking switch on the cell wall (which kept falling down) to “electrocute” your opponent. Yes live murder on PPV...yeah, right. This was a mass brawl with some gimmicky additions (the refer-eye camera helmet anyone?), including folk jumping out of coffins randomly placed in the cage, and talcum powder-faced people ready to cart a body off. This was pure mayhem from the get go and when Abdullah got zapped (as Cactus Jack inadvertently pulled the switch on his mate - after an awkward in-ring switcheroo) to end the match, a pyro display set off for effect, with flames and all sorts...and he was dead! Gasp! That is, before  he wasn’t and the “electrocuted” Abdullah rose from the chair post-match in a wild-eyed craze, kicked a stage hand or two and wondered off with Cactus Jack. This is a must-see occurrence in the wrestling foolishness hall of fame.

Death Matches have undergone countless configurations in promotions as far and wide but back in 1995, in Japan’s Kawasaki Stadium, IWA aimed to crown “the King of the Death Match” in a potentially fatal eight-man elimination tournament. Naturally it all came down to Cactus Jack and Terry Funk in the final - of course it did! On this night both Funk and Foley fought two times to get to the final and the brutality dished out was inhumane and forever lasting. However in the ludicrously titled No Rope, Barbed Wire, Explosive Barbed Wire Board, Time Bomb Death Match, both men showed why they are known as hardcore legends. C4 explosive barbed wire boards, blood, serious injury and an almost mythical depiction of violence ensued. The ring was supposed to even explode (as was custom in many matches of this ilk) but an issue led to pyrotechnics being used instead, leading to an angry crowd and Funk was none too happy either. The atmosphere was frantic, the match dangerous and the commitment to the craft incredible. Bodies were torn in barbed wire and, as Foley detailed in his autobiography Have A Nice Day, a shopping list of injuries and stitches were attained from this match, which saw him beat the legendary Terry Funk in the end. This match among many others earned Foley a respect in this business that knows no equal and continues now and ever more.

The 1992 Bungee Cord Match between Chaz Taylor and Steven Dane from the now defunct GWF is a piece of cult wrestling trivia still talked about, not especially favourably. The match came about as a result of Chaz feuding with Dane and agreeing to sign in any match where Dane’s manager cannot interfere, which led to the first and only ever bungee match...outside...in a car park. Classy touch. Both men enter a yellow cage, which is lifted just under 200 feet from the ground, and the battle begins. We see practically sod all, except the odd arm and leg flail about up in the night sky, despite the commentary team’s inexplicable enthusiasm. Eventually the combatants emerge into view, as Chaz looks like he’ll fall, before grabbing Dane and tossing him off the cage instead. As Dane is left to violently swing back and forth on the bungee cord for what seems like ages, the commentators scream and shout. Chaz may have won but frankly they both won here, by emerging alive and unscathed!

You’ll never see the likes of this again dear readers! In 1996 at BJW Summer Night’s Dream, Kazuo Sakurada (under the Kendo Nagasaki name) fought and defeated Mitsuhiro Matsunaga in an Amazon River Piranha & Barbed Wire Board Death Match (who thinks this stuff up?!). The objective to submerge your opponent in the piranha tank and cover it with the board. A bloody Matsunaga actually had a small hole bit into his chest as a result of being in the tank (the footage is scary) for just ten seconds or so. Remarkably, this match type actually took place again, at Wrestling Society X’s final unaired show in 2007, in a match between The Cartel and Los Pochos Guapos, but it is believed actual piranha were not used in that match.