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10 of the Greatest Matches from The Attitude Era

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The Attitude Era was a treasure trove of avant-garde matches that spanned the years between late 1997 and 2002. Arguably, it was the greatest era in sports entertainment and for good reason. Today, we take a look at ten of the greatest matches that defined the era and changed the business as it was previously known.

Shane McMahon vs. Steve Blackman—SummerSlam 2000

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Steve Blackman is perhaps one of the most underrated wrestlers of the Attitude Era. There will be a few underrated wrestlers from said era and beyond in this piece that weren’t as heralded as they should have been. Especially when looking back on matches like this one here.

It sheds an even further light on the types of matches that Shane McMahon was capable of having. If there’s something to be said about the McMahon family, and something positive, it’s that they would never ask their wrestlers to do anything that they wouldn’t do themselves, and Shane McMahon definitely proved that much in this match from SummerSlam 2000.

If you look back on the matches that Steve Blackman had during his time in WWE, you can see what he brought to the table every time he stepped into the ring—his martial arts techniques always showcased, and it was those techniques that be brought to the forefront in his arsenal of matches against the likes of Owen Hart and Ken Shamrock.


He was a technical wrestler that unfortunately didn’t come out of his shell and prove all that he was obviously capable of. They went the comedic route with him eventually, playing off of the old adage that someone who never cracks a smile can sometimes be the funniest of all.


There was nothing funny about this match, of course; except for Blackman’s face as he watches Shane take the bump, falling off of SummerSlam display siding and into oblivion.

Like I said, it was a precursor of things to come for McMahon, but falls like that aren’t seen all that often these days.


Stone Cold Steve Austin vs. Vince McMahon in a Steel Cage Match—St. Valentine’s Day Massacre (1999)

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And like I said, the McMahon’s weren’t ones to forego a hardcore match, or a Steel Cage Match, as was proven at St. Valentine’s Day Massacre in 1999.


It was in that very year that the business of professional wrestling was red hot and they primarily had Stone Cold Steve Austin and the dastardly boss man himself, the chairman of WWE, Vincent Kennedy McMahon to thank for that.

The two had a feud for the ages and it garnered quite a bit of attention. This resulted in countless matches; this one here perhaps being the best of the best, McMahon putting his life and his body on the line. Vince actually broke his tailbone in that match falling off the side of the cage and onto the announce table, and all before the match officially started.

Technically (meaning on a technical match basis), it wasn’t the best, but that’s not what we’re taking a look at here. When it came to these two, entertainment was what you were looking for, and that’s what they delivered every time out and especially in this match.

The New Age Outlaws vs. Cactus Jack & Chainsaw Charlie in a Dumpster Match—WrestleMania 14

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WrestleMania 14 makes this list twice, and it’s for very good reason both times over. In this one you had the New Age Outlaws, who had made the scene and were racking in some pretty impressive memories on WWE TV.

This match featured another duo that at the time didn’t need an introduction to the then jaded audience full of hardcore wrestling aficionados, especially fans of ECW, where both of these legends in this match had incredible portions of their careers.


This match didn’t disappoint in any department and the ingenious finish showcasing the cleverness of the OGs in the match has gone down in history, essentially cementing the legacies of one tandem and catapulting the other to superstardom in an era in professional wrestling that’ll hardly be forgotten.

Kurt Angle vs. Chris Benoit—Judgment Day (2001)

These two faced each other numerous times during their careers and it wasn’t at all the best match that they put on, but it helped define the potion of WWE’s roster at that time that could put on one heck of a technical wrestling match.


In the Attitude Era, the product was a tad watered down as far as technical wrestling was concerned, especially in favor of entertaining the casual fan, whom the Attitude Era catered most to.

The late Chris Benoit, along with Eddie Guerrero and Dean Malenko brought along with them a style of wrestling that hadn’t been seen in WWE since Bret hart and The British Bulldog, and Benoit put that style forth with another technical genius of the squared circle in Kurt Angle, 1996 Olympic Gold Medal winner.

Triple H vs. The Rock in a Ladder Match—SummerSlam 1998

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Many say that the greatest ladder match to be put on was the ladder match between Razor Ramon and Shawn Michaels at WrestleMania 10, and although Shawn Michaels is undoubtedly one of the greatest to ever step into the ring and dominate it as he did, I’d say that his buddy Trip definitely did it a tad better in this bout featuring The Rock.


It was in this era that The Rock was gaining steam, having started in the business only two years prior, but after finding success in a heel turn and a gimmick where he referenced himself in the third person, there was no one better that he could have faced in his run to be Intercontinental Champion than Triple H.

Stone Cold Steve Austin vs. The Rock—WrestleMania 15

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To stay on The Rock for a few more seconds, this match is an equally important piece of his history for him as much as it is for Steve.

For Steve, the match would come at an incredibly low point in his personal life, as he was going through a divorce from the mother of his two children, Jeanie Clarke, who also served as his valet back in the WCW days.

As for his character, Vince had put him through one heck of a grueling few months on the road to WrestleMania that year, which ultimately culminated in his victory and his reestablishing himself as the WWE Champion.

For The Rock, this was the build for his ultimate win over Steve at WrestleMania 19… “Act 3,” as Dwayne Johnson referenced to it himself in his promo before that match in 2003… “Everybody remembers act 3,” he said.

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