The 10 weirdest matches in WWE SummerSlam history

ASFN Admin

Administrator
Administrator
Moderator
Supporting Member
Joined
May 8, 2002
Posts
1,245,972
Reaction score
59
WWE SummerSlam is right around the corner, and for decades it's been billed as "the biggest party of the summer." For many wrestling fans, it's the second-biggest event on the WWE calendar behind WrestleMania. That status feels even more locked in now that SummerSlam has grown into a two-night event.

This year's edition in Minneapolis features a rather unexpected attraction: Gunther against "WWE SmackDown" general manager Nick Aldis.

In just the last calendar year, Gunther has retired legends Goldberg, John Cena and AJ Styles, continuing one of the most dominant runs in company history. But after a WrestleMania 42 match with Seth Rollins that felt undercut, I expected something bigger for "The Ring General" here. Perhaps a World Championship match, something with some major main-event stakes. Instead, however, he finds himself opposite the "SmackDown" GM, Aldis, who has not had a match in WWE since joining the company in 2023.

The pairing feels odd, even if it does pay off their ongoing story. But the announcement sent me down a different road, thinking about the strangest matches this show has ever produced. SummerSlam, after all, is where supernatural happenings take place and where bizarre stipulations go to from concept to execution.

So let's look back at what I believe to be the 10 weirdest SummerSlam matches of all time.

No. 10: "The Fiend" Bray Wyatt vs. Braun Strowman: Falls Count Anywhere Match (SummerSlam 2020)


If there was ever a year built for strange wrestling, it was 2020. The COVID-19 pandemic shut down live events, yet professional wrestling was deemed an essential business. WWE kept producing weekly television inside its "ThunderDome," an arena painted with walls of LED screens showing fans watching from home. The presentation alone felt like something out of 1984. Then came this main event: Braun Strowman defending the Universal Championship against "The Fiend" Bray Wyatt in a Falls Count Anywhere match.


This came during the most polarizing stretch of Wyatt's career. The Fiend was one of WWE's most compelling characters, but the supernatural layers of the gimmick often buried how good Wyatt was between the ropes. It also made him nearly impossible to book, as the widely panned Hell in a Cell match against Seth Rollins the year before had already proven. Strowman, meanwhile, was fresh off beating Goldberg for the title at WrestleMania 36 and looked poised to plant himself in the main-event scene for good.

The match was as odd as advertised. Critics weren't impressed either; Dave Meltzer of the Wrestling Observer Newsletter gave it one star, the lowest rating on the card. And yet it's remembered less for anything between the bells than for what came after The Fiend won the strap: Roman Reigns returned from nearly five months away, laid out both men and stood in the middle of the ring holding a title he hadn't wrestled for.

That was the beginning of "The Tribal Chief."

No. 9: Hulk Hogan vs. Shawn Michaels (SummerSlam 2005)


Legend versus icon. Hulk Hogan, arguably the biggest star in wrestling history, against Shawn Michaels, who by 2005 had cemented himself as "Mr. WrestleMania" and one of the greatest in-ring performers of all time.

What's interesting is that this rivalry wasn't supposed to be one-and-done. The reported plan was a trilogy, with each man taking a win before a decisive third match. Somewhere along the way, that fell apart. Hogan still seemed to see Michaels the way he had a decade earlier, as the tag-team guy from The Rockers. Michaels knew exactly what he'd become by 2005, and it wasn't that.

Hogan reportedly had no interest in losing to him, so creative turned Michaels heel instead, ending a long babyface run that had started with his in-ring return at SummerSlam 2002. The turn produced some of the best promo work of Shawn's second run — the best of which was a Larry King parody, when Michaels, dressed as Hogan, said he was a great guy whenever the cameras were rolling, "but when the cameras go off, brother, it's another story. Brother, brother, brother."


The match is still an entertaining watch, just not for the reasons anyone expected. Whether he was making a point or simply leaning into the moment, Michaels sold Hogan's offense like Wile E. Coyote taking a run at the Road Runner. He flew across the ring at the lightest jab from Hogan and launched himself into the air on the big boot before jumping off the mat and falling again.

Instead of the strait-laced WrestleMania-style classic fans wanted, this one turned into a parody of Hulkamania. Michaels' overselling reduced Hogan's signature comeback to a "Saturday Night Live" sketch. Anyone who knew the backstage story understood immediately. Everyone else just wondered why Michaels was ricocheting around the ring like a pinball. It's remembered now as a case of Hogan's politics spilling directly into a match, and that is exactly what lands it on this list.


No. 8: The Rock vs. Billy Gunn: Kiss My Ass Match (SummerSlam 1999)


File this one under not only one of the weirdest matches in SummerSlam history, but one of the strangest stipulations the company has ever produced.

In 1999, the WWF was trying to push Billy Gunn past his role as the muscle of the New Age Outlaws and into a real singles run. He won King of the Ring that June and looked headed for the main event. During his rise, he faced off with The Rock, who was at the absolute height of his powers and spent weeks delivering some of the funniest and most scathing promos of his career — at Gunn's expense.


The build was something to be noted here. The Rock had poison ivy applied to Gunn during an on-camera massage segment. Gunn answered by shoving The Rock's face into his own backside. That escalated into a Kiss My Ass Match at SummerSlam, where Gunn brought a large, cloaked woman as his valet. Rock rammed Gunn's face into her hind parts, hit the People's Elbow and won.

Classic Vince Russo-era gimmick booking. Crash TV not at its best, but absolutely at its weirdest.

No. 7: Hulk Hogan & Brutus "The Barber" Beefcake vs. Randy Savage & Zeus (SummerSlam 1989)


In 1989, WWF released the film "No Holds Barred," its first real attempt to cash in on Hulk Hogan's crossover appeal, decades before WWE Studios existed. Hogan had already dipped a toe into acting as Thunderlips in "Rocky III," and Vince McMahon believed his biggest star could carry an action movie of his own. To play the villain, the film introduced Zeus, portrayed by Tiny Lister Jr., who a different generation eventually came to know as Deebo in "Friday."

Rather than leave Zeus on screen, the WWF did something that felt unprecedented at the time: it made a movie character into an on-screen and in-ring performer. Zeus became Hogan's newest rival and eventually teamed with Randy Savage to face Hogan and Brutus "The Barber" Beefcake in the SummerSlam main event at the Meadowlands. Lister, mind you, had no wrestling background at all. Whatever he knew, he learned on a movie set.


In other words, fans were being asked to accept a film villain as a legitimate main-event attraction. The New Jersey crowd went along with it, but the match never came close to what a SummerSlam main event should be.

The rivalry didn't end there. Hogan and Beefcake met Savage and Zeus again inside a steel cage on WWF's No Holds Barred pay-per-view that December. Taking a step back, the whole experiment is hard not to admire. Wrestling has never been shy about borrowing from Hollywood; it just rarely borrows the actual actor.

No. 6: Ken Shamrock vs. Owen Hart, Lion's Den Match (SummerSlam 1998)


Long before the Fight Pit in NXT, or Ronda Rousey and Shayna Bazler's "MMA Rules" battle, there was the original Lion's Den Match at SummerSlam 1998 — an enclosed, cage-like pit with no ropes, where the only way to win was by submission or knockout.

The concept was made for a rising star, Ken Shamrock. Before MMA went mainstream, Shamrock was one of the faces of the early UFC tournaments. He had pro-wrestling experience before he ever fought professionally, but fans knew him as a shoot-fighter first, and WWF leaned all the way into it making him "The World's Most Dangerous Man."

You must be registered for see images attach

Ken Shamrock was the first crossover star to bridge the worlds of UFC and WWE.
Ross Dettman via Getty Images

Shamrock was the obvious choice for a match like this; Owen Hart, however, was not. When you picture a shoot fight, Hart wasn't the first name that came to mind. But he had one of the sharpest minds the business produced, and that high in-ring IQ let him adapt to this match type. Shamrock won the match, and it was competitive enough to justify the gimmick.

The presentation was still strange, though. A UFC-style cage parked off to the side of the entrance ramp, instead of a ring in the middle of the arena, is a hard sell for a major SummerSlam attraction. It was unconventional. It also worked far better here than it did a year later.

No. 5: Ken Shamrock vs. Steve Blackman, Lion's Den Weapons Match (SummerSlam 1999)


By the summer of 1999, Vince Russo's influence on WWF creative had peaked. Hardcore wrestling was everywhere, ECW had reset the industry's expectations, the Hardcore Championship was a weekly attraction and nearly every feud required a stipulation. SummerSlam 1999 is the evidence of that notion.


Shamrock and Steve Blackman were genuinely the right two men for a Lion's Den Match. Left alone, it could have been the most realistic "fight" on the card. But … they didn't leave it alone. The company added weapons, and the moment kendo sticks came into the Den, it stopped being a fight and became one more Attitude Era gimmick.

SummerSlam 1999 also gave us a Greenwich Street Fight between Test and Shane McMahon, the aforementioned Kiss My Ass Match, a Tag Team Turmoil Match, and a Triple Threat main event between Steve Austin, Triple H and Mankind with Jesse Ventura as special referee. Everywhere you looked, a gimmick, brother.

No. 4: The Big Boss Man vs. The Mountie, Jailhouse Match (SummerSlam 1991)


I'm a fan of the Big Boss Man. His original run in the late 1980s and early 1990s, his later work as Vince McMahon's enforcer during the Attitude Era — it didn't matter. Boss Man committed completely, every time.

Part of what made the character land is that Ray Traylor had actually worked as a corrections officer in Cobb County, Georgia. That gave him a hard edge that held up even during one of the company's most cartoonish stretches.

Across from him was Jacques Rougeau as The Mountie, a character every bit as ridiculous as it was entertaining. After a strong tag run, Rougeau reinvented himself as an arrogant Canadian lawman whose catchphrase was, "The Mountie always gets his man."

An American corrections officer against a Canadian Mountie? The only logical stipulation is a Jailhouse Match — and at SummerSlam 1991 inside Madison Square Garden, the first and only one took place. The rules were wonderfully simple: loser spends the night in jail.


Boss Man won. WWF cameras then followed The Mountie through an entire arrest and booking at a real New York City precinct, handcuffing, fingerprinting and all.

This was never meant to be a technical masterpiece. In fact, I couldn't tell you anything about the actual match. What I remember is The Mountie getting hauled off to jail afterward. Super weird, but it fit that cartoonish period in the WWF.

No. 3: Mankind vs. The Undertaker, Boiler Room Brawl (SummerSlam 1996)


The Undertaker was built for gimmick matches. Throughout his career, the WWF used him as the centerpiece for nearly every stipulation it wanted to test. Casket Match, Buried Alive Match, Inferno Match, Bodybag Match, Last Ride Match, Hell in a Cell, and even a Paul Bearer in a Cement Coffin Handicap Match.

Mankind was the ideal opponent for such an experiment. This was still the early Mick Foley character, years before the Rock 'n' Sock Connection turned him into one of wrestling's great comedic babyfaces. In 1996 he was unpredictable and genuinely disturbed, and that shrieking promo voice made it easy to believe he'd be at home in whatever environment the company dreamed up. Like, say, a boiler room?


Which is where this one started. The match opened deep inside the arena's boiler room rather than the ring, and the only way to win was to escape and take Paul Bearer's urn. Bearer turned on The Deadman and aligned himself with Mankind, a feud that lasted for years, eventually giving us their infamous Hell in a Cell match.

The timing of this one should be pointed out. SummerSlam 1996 came just weeks after Hogan turned heel at Bash at the Beach and formed the New World Order in WCW, and the WWF was suddenly under real pressure to be interesting. The Boiler Room Brawl wasn't a direct answer, but it showed a company willing to think outside its proverbial box and attempt to draw an audience. The Attitude Era was just beginning to brew and they pulled off its cinematic-style matches years before anyone had a name for it. The Boneyard Match between Taker and AJ Styles at WrestleMania 36 owes this one a debt.

No. 2: Rey Mysterio vs. Eddie Guerrero, Custody of Dominik Ladder Match (SummerSlam 2005)


"I am your Papi!" might be the most infamous words Eddie Guerrero ever said, screamed at a young Dominik Mysterio in the middle of one of the most outrageous storylines of the Ruthless Aggression Era. You see, Guerrero claimed that he, rather than Rey Mysterio, was Dominik's biological father.

These two were real-life friends and one-time WWE Tag Team Champions who made magic in the ring at WrestleMania 21 earlier in the year. But their friendship went awry by the time SummerSlam arrived, and this feud went in the direction of a daytime soap opera. But this wasn't "Days of our Lives," it was SummerSlam.


Instead of a championship, Mysterio and Guerrero fought over custody of 8-year-old Dominik. The legal papers naming the boy's father hung above the ring, and the only way to win was to climb a ladder and pull them down. Dominik got physically involved that night, climbing up to shake Eddie loose, and with help from Eddie's real-life wife Vickie Guerrero, Rey took the papers and won custody of his own son.

Rey has said the idea came from Eddie himself. At one point the pitch was to suspend Dominik above the ring instead of the papers, which thankfully never happened. Eddie understood the angle would get people talking and draw money precisely because it went too far. It's tabloid absurdity in every conceivable way

This is still one of the most talked-about matches in the show's history. The sheer absurdity of professional wrestling never stops amazing me, and this rivalry might be the purest example of why. If someone who has never watched a match asked me to explain what makes this form of entertainment unique, I'd show them this.

No. 1: The Undertaker vs. The Undertaker (SummerSlam 1994)


I told you the Undertaker was built for gimmick matches. Nothing proves it better than the strangest match SummerSlam has ever booked: The Undertaker vs. The Undertaker.

After losing a Casket Match to Yokozuna at the 1994 Royal Rumble, Undertaker vanished from WWF television for months, nursing a real injury. In his absence, Ted DiBiase produced what he insisted was the "real" Undertaker, played by Brian Lee, who did a genuinely convincing job of replicating the Deadman's look and mannerisms. All the while, Paul Bearer kept insisting the true Undertaker would return.

WWF went all-in heading into SummerSlam 1994 trying to find The Undertaker. Leslie Nielsen, riding a "Naked Gun" wave, turned up in a run of vignettes as a detective hunting the missing Undertaker. Week after week, the investigation continued … until the original Deadman finally walked back through the curtain at the United Center in Chicago.


This match was never about the match, but about the sight of two identical Undertakers standing across the ring from one another. Character spectacle over match quality was the norm for WWF at the time.

The Undertaker vs. The Undertaker isn't a wrestling classic and was never going to be. It's remembered because we watched two supernatural morticians fight over which one of them was the superior supernatural mortician. Wrestling in a nutshell.

That, more than anything, is what SummerSlam has always been. A showcase for spectacle. Whether it's Brock Lesnar lifting the ring with a tractor in 2022 or Gunther facing a general manager in Minneapolis this year, this is the show where WWE takes the big swing. History says this one will be unforgettable and wonderfully weird.

Continue reading...
 
Top