When two wrestlers are engaged in a hot feud that’s igniting the territory, there will usually be a match with some sort of stipulation match to blow off the feud. Normally, these stipulations will be for a prestigious world title or a chance for a world title that bring fond memories to fans' hearts and minds.
However, then there are matches where the stipulation is so comical or terrible that they bring about looks of disgust on fans faces. If wrestling at its heart is about the struggle between good vs. evil, so it's natural to try and spice that up every now and again. So, sometimes, bookers think that a steel cage match has been done to death (and they have been but are genuinely always welcome), so they think there's a need to reinvent the wheel.
Wrestling has its roots in the Carnival / Sideshow / Vaudeville world where anything and everything went, so it’s no wonder that all kinds of bookers would try all kinds of ways to put a butt every eighteen inches. Here’s 15 dumb ways they tried.
13 Cry Baby Match
The 1–2–3 Kid had turned on Razor Ramon at the Royal Rumble, costing him the Intercontinental Championship and had been taunting him ever since by strolling to the ring during his matches with a stroller. Hence, the first, and thankfully last, Cry Baby match at In Your House 6, where the two Kliq members would do battle, only this time the loser would be diapered and fed a bottle by the winner. Out of all of the “loser gets humiliated” matches, this one has actually got to be the best, even though it was incredibly dumb, just because the fans didn't have to see someone’s backside or disgusting foot.
12 Custody of Dominick Ladder Match
Anytime Rey Mysterio and Eddie Guerrero locked horns, it was something special. Their match at Halloween Havoc 1997 is heralded as one of the greatest matches of all time. The stage was set for another world class battle between the two at Summerslam 2005, but this time in a ladder match. The match was a very good showing, but the stipulation and the storyline made it bad. Wrestling matches for careers, titles, valet services, or masks are one thing, but custody of a child is a whole different affair and this ventured into Springer territory.
11 The Title Can Change Hands on a DQ
When Superstars and Divas battle for a championship, there are two ways to win–pin your opponent or make them tap. Heel champions use that rule to their advantage and get counted out or disqualified to keep their title. Sometimes, that rule gets changed in order to make the heel have to fight, so they usually have a no DQ match that will involve weapons and a little more intrigue. At WrestleMania XXV, they implemented a rule into the Randy Orton/Triple H main event, where the title could change hands on a DQ. The build to this match was awesome and fans wanted to see them go after each other in a No Disqualification match, not a weird stipulation that didn't add much to the match.
10 Control of the Company
Can you imagine Tim Cook vs. Arthur Levinson in a San Francisco Strap Match for control of Apple? How about the Steinbrenner brothers in a New York City Street Fight for the future of the Yankees? However, for some strange reason, in wrestling, people are allowed to duke it out for control of the company. Whenever this dopey idea pops up in wrestling, it seems to be accepted. Especially in the WWE, where we all know Vince McMahon runs the show and probably will until he physically can’t, so it's hard to suspend disbelief with these kinds of matches.
9 Concrete Crypt
The Undertaker was a sight to behold and the last great character from the cartoony Hogan era. His manager and friend, Paul Bearer, was equally creepy. When Taker returned as the Deadman in 2004, Bearer came with him but was kidnapped by The Dudleys, who fought The Undertaker in a handicapped match at the Great American Bash. Per the match stipulation, if Taker lost, Paul Bearer would be cemented in a glass crypt, which was dumb enough since we’re not going to watch a man be murdered at a wrestling show. Sadly, it got even worse when The Undertaker won and, for some unknown reason, buried his friend anyway.
8 Pink Slip on a Pole
A variant on the Loser Leaves Town match back in 1999, the match was between the Rock n’ Sock Connection. When most people get a pink slip, they’re unfortunately being fired, but in this match, it was guy who grabbed the pink slip that kept their job. If that’s not strange enough for you, Mick Foley asked for the decision to be reversed after interference from Al Snow and ended up losing. However, a few days later, The Rock asked for the decision to be reversed. Pole matches and convoluted booking was usually WCW’s bread and butter, but it was WWE doing the honors here.
9. Hair vs. Hair
In the “Only to Amuse Vince” category, we have Eugene vs. “Uncle Eric,” at the inaugural Taboo Tuesday where the fans would vote on the loser’s fate. In what has to be most likely the most overbooked two minutes in wrestling history, Eugene pinned Bischoff and the fans voted for his head to be shaved. Coach, trying to lie to Eugene, had convinced him that the fans voted that Bischoff would be Eugene’s servants for five minutes, but Vince threatened to fire Bischoff if he didn’t get a haircut. As if hair vs. hair isn’t silly enough, this one just went a long way to embarrass a former rival.
7 Flag Match
When the big heel from another country dominates a territory and begin waving his nation’s flag, it’s time for the big American babyface to step up, Stars and Stripes in tow and have a good ol’ fashion flag match, where the winner gets to have their flag hoisted over the arena. Seldom does the heel win (the Harts and Rusev in recent memory), so it’s just an excuse to waive Ol’ Glory during the show. There's an even more foolish variant to this match, where sometimes the winner has their national anthem played.
6 Last Chance Challenge
The Last Chance Challenge is the most confusing match stipulation on this list. The match is a championship match, where if the challenger fails to the win the title, one of two cases can happen – they can never challenge for the title again or they can never challenge for the title again, so long as that person is champion. It gets a little strange when the challenger still is allowed to enter into contests like the Royal Rumble, #1 contender tournaments and other matches that could find ways to circumvent this not–dramatic–at–all–but–we’re–supposed–to–think–it–is stipulation.
5 Loser Wears A Dress
Bookers love to put wrestlers in dresses and see how they deal with it. Brian Pillman lost to Goldust and had to wear a dress until he won a match. Then, Saturn lost to Chris Jericho amd started wearing Goth dresses and enjoyed the comforts of wearing a dress. Two grown men fighting one another to not have to wear a dress... do they hate each other so much that either man can’t reconcile their differences long enough to not have to have this dumb stipulation included?
4 Loser Has to Work for Winner
Brian Pillman fought Goldust again, this time if Pillman won, Marlena would be his assistant for a month. The Bellas battled and when Brie lost, she had to be Nikki’s personal assistant for a month. There are a multitude of issues with this concept. The worst problem is that in hindsight Pillman had an unwilling partner for a month and with the Bellas, the whole angle was dropped because apparently we fans can’t remember anything that happened yesterday and Vince decided the Bellas didn’t need to be divided anymore. At WCW Fall Brawl 1998, Saturn avoided having to be Raven’s slave by beating him, which meant the Flock had to disband, but what if they liked looking like vagrants and following Raven around?
4. Battle for Trademark Rights
When D-X split up in 1999, X–Pac and Road Dogg fought Chyna and Billy Gunn for the rights to the D-X name and brand, in a snoozefest of a feud with a ridiculous stipulation for the last match.
Speaking of D-X alumni, were we supposed to believe that Shawn Michaels mismanaged his funds so much that he had to seek help from the evil JBL and that they would fight over the rights and career of HBK? Some stipulations are easier to believe than others and battles over branding are too ridiculous to believe, so these storylines pretty much fell flat.
3 Loser Goes to Jail (Mountie vs. Bossman)
This stupid stipulation only ever came up once at SummerSlam 1991, because the participants were both law enforcers, get it? The righteous and true Big Boss Man and the villainous Mountie went head to head with the loser having to spend 24 hours in a NYC jail. One would think that spending a night in jail would scare The Mountie straight, but instead he fought the NYPD at every turn while being fingerprinted and tossed in a cell. Thankfully, the Jailhouse Match was a one and done event.
2 Gulf of Mexico Match (Chavo vs. Punk)
WWE braintrust thought this would a classic, a match where you have to toss your opponent into a body of water to win, but not just any body–the Gulf of Mexico. ECW was in gulf–bordering Corpus Christie, TX when this match between CM Punk and Chavo Guerreo took place. The match started in the arena, so they had to brawl all the way outside. Hardcore matches are fun, but unless one of these guys had super strength to toss their opponent from the ring to the water, shouldn’t they have just started outside?
1 Kiss My (Insert Body Part Here) Match
The dumbest stipulation ever is a humiliating loss for the fans as well. It’s hard to convince non–watching friends how viable this sport is when WWE continues to have matches where the loser has to kiss the winner’s ass. Even worse was watching build–up to the anticipated Bret Hart/Jerry Lawler Kiss My Foot Match, where we had to sit through Lawler putting his feet into the grossest things imaginable. At least the match was good and Lawler wound up kissing his own foot. A worse match happened almost 20 years later when Michael Cole had to kiss the King’s foot, dipped in J.R.’s BBQ sauce.