The 10 most awesome moments in WWE SummerSlam history

In a bit of trivia to make you feel old, SummerSlam turns 30 years old in 2018. Shockingly, WWE hasn’t yet advertised it as “The 30th anniversary” like they usually do — for a company that just signed a billion dollar deal, math doesn’t seem to be their strong suit. 

Regardless, I’ve been watching wrestling for a long time, and I’ve followed the history of SummerSlam from the beginning in 1988 to where we are today, and there’s been some huge moments and great matches.

I’ve already done a million different “Best matches” lists, so this is more of a listing of 10 cool, memorable and downright awesome moments that we all remember long after the show is over. To keep things fair, we’ll do this in chronological order.  Buckle up!

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SummerSlam 1988

The show that kicked everything off, featuring one of the all-time defining moments for the promotion: Honky Tonk Man had held the Intercontinental title for a mind-numbing year-and-a-half, getting himself disqualified and counted out and cheating his way into retaining it against all challengers. Until, finally, he talked himself into an open challenge to anyone in the back at SummerSlam, resulting in Ultimate Warrior storming down to the ring and destroying him to win the title for the first time.

Whereas everyone else had overthought the problem and tried to outsmart Honky, Warrior simply cut the Gordian Knot and beat the hell out of him before he ever had a chance to cheat and save his title. A strategy brilliant in its simplicity, which made Warrior into an instant main eventer. 

SummerSlam 1990

A moment sadly apropos this week, as the Hart Foundation completed their comeback from failed singles pushes all the way to WWF Tag Team champions again, defeating Demolition in a memorable 2-out-of-3 Falls match to claim their second and final title. Demolition had recently begun using a three-man team with new member Crush (under the “Freebird rule” of tag title defenses) and cheating like crazy as a result, leading to the Harts challenging for the belt as huge underdogs.

However, some timely distraction from the debuting Legion of Doom resulted in Crush getting rolled up and pinned, sending the Philly crowd into hysterics. Jim Neidhart’s gleeful cackle after the victory remains a highlight of his career and one of my favorite moments. 

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SummerSlam 1991

Although the actual match between the Mountie and the Big Bossman in MSG wasn’t particularly memorable on its own, it was the stipulation that keeps people talking about it today. The loser of the match would have to spend a night in a New York City jail, and after Mountie spent most of the evening taunting and insulting the NYPD, he proceeded to lose and get hauled off to the pokey.

Mountie got all his abuse thrown right back at him, all the way from fingerprinting to meeting his new cellmate for the evening.

SummerSlam 1992

I mean, although I didn’t specifically want to do a list of great matches, you kind of have to include the British Bulldog’s amazing five-star match with Bret Hart, as he won the Intercontinental title in a sold-out Wembley Stadium in front of 80,000 of his people. All the more impressive considering Bulldog’s injury issues and noted drug problems at that point, which left Bret having to carry the entire match on his own.

SummerSlam 1993

Not my favorite — or anyone’s favorite — SummerSlam by any means, but the undisputed show-stealer in ’93 was Bret Hart’s showdown with Jerry “The King” Lawler, which was sadly delayed by Lawler having to rescue a busload of nuns from a horrific car accident, resulting in a leg injury that put Doink the Clown into the match in his place.

Lawler’s amazing pre-match story, combined with Hart destroying the clown and then finally getting Lawler in the ring after months of trash-talking, made for an instant classic. Although Bret lost the match due to cranking on the Sharpshooter until he got disqualified, I don’t think anyone was particularly disappointed in Lawler finally getting what was coming to him. 

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SummerSlam 1998

Jumping ahead a bit, 1998 was a real comeback show for the WWF, as the past few SummerSlams tanked on PPV, but their return to Madison Square Garden really energized the show. My favorite moment is the Ladder match between the Rock and Triple H, which was great on its own, but more importantly made both guys into much bigger stars than they were coming in. That’s always the goal for these kinds of matches, although I don’t think anyone suspected just how huge of a star that Rock would quickly become, as he was almost instantly turned into a babyface by the New York crowd based on his amazing performance here, even in the loss.

But the Rock always was someone who could bounce back from a loss as a bigger star than ever.

SummerSlam 1999

Another match that made both participants bigger stars happened the next year, with the admittedly silly romance between Test and Stephanie McMahon leading to a showdown against … her brother?

Yeah, it was a literal soap opera plot, but Shane McMahon suddenly made it hilariously fun by bringing in his ridiculous backup in the form of the “Mean Street Posse,” three friends of his from Greenwich who were absolutely no threat but threw themselves into the role with such enthusiasm that it couldn’t help but get over.

The “Love Her or Leave Her” match itself was much better than expected, with Test overcoming all the ridiculously stacked odds and interference to emerge victorious, earning the respect of the family as a result. Unfortunately, Test wasn’t able to ride that momentum into anything later on, but he’ll always have that match to be remembered by.

SummerSlam 2000

OK, well, another great match wins by default here, as everyone’s favorite trio of teams (Edge & Christian, The Dudley Boyz and the Hardy Boyz) proceed to invent the Tables, Ladders and Chairs match and shorten their careers for our pleasure, diving off stuff and smashing stuff into each other and generally being awesome.

Unfortunately Edge and Christian both ended up retired years early and Matt Hardy is kind of a mess these days, but man this was great.

SummerSlam 2002

At the time we were all a bit skeptical about the comeback of Shawn Michaels, who had been out for four years and was now claiming that the healing power of religion had fixed his back. But Shawn is no one if not someone who delivers in the big matches, and boy did he ever deliver in his street fight with frenemy Triple H.

They destroyed each other for 20-plus minutes, using all the smoke and mirrors and weapons available to them, stealing the show from everyone else.

What was only supposed to be a one-time comeback soon stretched into two, and then ended up being an entire second career for him, lasting another eight years before ending at the hands of the Undertaker.

SummerSlam 2005

Speaking of Shawn delivering in the big matches, 2005 saw Hulk Hogan making yet another comeback, leading to a dream match with Michaels that headlined the show that year. Unfortunately, Shawn and Hulk had a philosophical disagreement about how the proposed series of matches between them should go, leading to Shawn putting on perhaps the greatest bad match in history.

He spent the entire match silently protesting Hulk’s ego by flying all over the ring in exaggerated manner, flailing around like a ragdoll and acting like a cartoon character before succumbing to the big boot and leg drop. What could have been a forgettable loss suddenly became a memorably hilarious middle finger to Hulkamania, brother.

So there we have 10 of my personal favorite memories from the show. Stay tuned for the counterpoint, as I look at 10 of the most memorably awful moments next time!