WWE in the 1990s: 10 iconic, era-defining photos and the stories behind them

Two of WWE's biggest 90s stars, Stone Cold Steve Austin and The Undertaker met at Summerslam in 1998
Two of WWE's biggest 90s stars, Stone Cold Steve Austin and The Undertaker met at Summerslam in 1998

The 1990s are, for many fans, the definitive decade in professional wrestling. From the dawn of the Attitude Era to the peak of the war with WCW, it was the decade that had it all.

Comparing the ringing in of 1990 to the final days of 1999 draws arguably the biggest contrast of any period in the industry as the slow, deliberate, and exaggerated style so famed in the 1980s gave way to a higher-paced, athleticism-based product that now so clearly defines the decade.

In WWE or, as it was in 20+ years ago, the WWF, the 1990s produced some of the most thrilling matches, compelling stories, unforgettable moments and, sadly, some real tragedy. It was the decade that gave us The Undertaker, Bret Hart, and Stone Cold Steve Austin, and the ten-year span that saw wrestling once again enter the mainstream thanks to celbrities like Mike Tyson and huge acts like D-Generation X and the aforementioned Steve Austin.

Trying to surmise an entire decade so steeped in history into just ten photos has been no easy task, but for the ideal trip down memory lane, here is a selection of snaps that will have you dining out on nostalgia for the rest of the day.


#10 Brother vs. Brother

This clash opened arguably the greatest Wrestlemania of the 1990s and, perhaps, of all time.
This clash opened arguably the greatest Wrestlemania of the 1990s and, perhaps, of all time.

As WWF Champion for long spells in 1994, 1996, and 1997, it would be fair to say that Bret Hart's status as the premier wrestler of the 1990s is unquestioned. Despite his various victories and memorable encounters, however, Hart actually features various times in our ten-image collection in losing efforts - not least here, against his own brother, Owen.

Owen Hart, Bret recalled many years later, had been considering retiring from wrestling in 1993 after failing to really establish himself in the company. Bret would convince Vince McMahon to pair the two in a 'sibling rivalry' storyline that would go on to produce some of the best stories and matches of 1994 and beyond.

This image shows Bret and Owen opening the show at Wrestlemania X at Madison Square Garden, the birthplace of WrestleMania. Thanks to an ingenious pinning combination after his elder brother had attempted a victory roll, the youngest of all the Hart siblings picked up what would be the biggest win of his career. Owen would, of course, tragically pass away at the end of the decade after an accident at a pay-per-view event. This is one bout for which he'll be forever remembered.

#9 International 'Mania

The Ultimate Warrior and Hulk Hogan lock horns in 1990.
The Ultimate Warrior and Hulk Hogan lock horns in 1990.

Throughout the 1980s, Hulkamania ran wild in WWE as Hulk Hogan established himself at the top of the company, and helped establish Vince McMahon's empire in the mainstream. From t-shirts, to movies, commercials, music albums, and a whole lot more, Hogan was very much the top dog in the worldwide professional wrestling industry.

As the 80s gave way to the 1990s, however, Hogan's powers were thought to be on the wane, with heads turned by the arrival and explosion into prominence of the Ultimate Warrior.

The Warrior was already Intercontinental Champion, but was believed by many to be, ultimately (pun intended), the figure who would assume Hogan's mantle and keep WWE at the forefront of the industry into the next generation. This image captures a moment during their iconic meeting at 1990's Wrestlemania VI. It was the first time 'Mania had been held outside of the United States, as it emanated from the SkyDome in Toronto, Ontario, Canada, with a huge crowd watching on as the face-painted, frenzied challenger snared the title from Hogan in what was seen, at the time, as a definitive passing of the torch moment. That did not end up turning out to be true, but the match stands out as iconic nonetheless.

#8 Shawn's swansong

Shawn Michaels bowed out of the WWF in 1998 after this effort against Stone Cold Steve Austin.
Shawn Michaels bowed out of the WWF in 1998 after this effort against Stone Cold Steve Austin.

If, earlier, we noted Bret Hart as the ultimate wrestler of the 1990s then, surely, the moniker of 'greatest entertainer' of the decade has to go to Shawn Michaels.

The Heartbreak Kid is, today, a celebrated, decorated two-time Hall of Famer and comfortably agreed upon as one of the greatest of all time. Much of what earned him that reputation came between 1990 and 1998, a period in which he would both establish himself in WWE, and bow out - at least for a while.

The third entry in our collection was taken just before what would be his last match of the 1990s, and at the time believed to be his final match, period. With countless classics behind him, this outing against Stone Cold Steve Austin at Wrestlemania XIV certainly won't go down in the 'Vintage Michaels' category, but it was a pivotal moment in so much as it crowned Austin as WWE Champion and truly ushered in the Attitude Era that Michaels had done so much to start.

Michaels' back issues and overall health meant he was, by his own standards, in a state of decline by the time he reached this 1998 battle with the Texas Rattlesnake. Afterward, he would go on to take a break from the ring that, miraculuously, he returned from after just short of 4 and a half years away.

#7 "Is Hulkamania dead?"

Hulk Hogan is blasted by a 'photographer' at King of the Ring 1993
Hulk Hogan is blasted by a 'photographer' at King of the Ring 1993

Those were the very words uttered by a shocked commentator, Jim Ross, as viewers attempted to soldier on through the broadcast of WWE's 1993 King of the Ring pay-per-view after having just seen Hulk Hogan assaulted in horrific fashion.

Come '93, Hogan's already unsteady status as a full-time performer in the company was starting to raise its head as a problem. Knowing that he was ultimately destined for movies, acting and - as it transpired - WCW, Vince McMahon needed a way to move Hogan out of the spotlight and to get the title on Yokozuna, WWE's choice to be the dominant heel of the new generation. While there was no love lost between Hogan and McMahon, the Chairman of the Board did not want to lose or destroy the power and status that Hulkamania had amassed for his promotion over the prior ten years.

The plan, then, was for Yokozuna to claim the belt in typically heelish fashion, leaving Hogan's reputation as a superhero relatively in tact in the eyes of fans. They opted to have a 'photographer' hop up on to the apron to take an ill-timed photo with Hogan, who had been shaping up to put Yokozuna away at the match's conclusion. At that moment, though, the would-be snapper's camera 'exploded' right in the champ's face, leaving him, it appeared, totally blind. Visually, the explosion was convincing, even if Hogan's selling was less so! Unlike in late 1991 when The Undertaker defeated Hogan to win the WWF Championship, this truly was the end of Hulkamania (at least for 9 years). Hogan wrestled for the WWF for the next two months, mostly during the company's European tour, but was not seen on TV again until 2002.

#6 The Bulldog's best day

The British Bulldog contemplates the biggest win of his WWE career
The British Bulldog contemplates the biggest win of his WWE career

Every dog, they say, has its day. Few can dispute that for Davey Boy Smith, the British Bulldog's best day came in 1992 at SummerSlam.

That night at Wembley Stadium in London, England, more than 80,000 of the Bulldog's compatriots roared him on to victory against his very own brother-in-law, Bret Hart, in the main event. He would capture the Intercontinental Championship for the first and only time. It was Smith's first big WWE win as a singles star, and his only major singles title win. He had short stints as European and Hardcore Champion in the late 90s after departing and returning to the company for a final run.

The image perfectly captures the story of the match and, indeed, the night. The realisation on Davey's face that he has indeed accomplished such a feat, and Bret's recognition of exactly the opposite. So much is tragic about the image, too, given the Bulldog died at the age of just 39 only ten years later in 2002 a few months shy of the 10th anniversay of the big victory, having never again reached the heights of this very special night in London.

#5 Bearer does the unthinkable

Paul Bearer heartbreakingly turns on The Undertaker at the 1996 edition of Summerslam
Paul Bearer heartbreakingly turns on The Undertaker at the 1996 edition of Summerslam

For fans of WWE in the 1990s, The Undertaker and Paul Bearer were so closely aligned, it is almost difficult to remember that they actually split in 1996 after Bearer turned heel on the Deadman at that year's SummerSlam.

Undertaker had first been introduced to WWE by Ted DiBiase, who quickly moved him to the tutelage and guidance of Brother Love. Love then in turn decided he was just a little too busy to steer the career of the Undertaker, who'd go on to become arguably WWE's greatest ever character. Instead, he introduced us to Paul Bearer, the pale faced, high-pitched mortician as the man who'd lead 'Taker going forward. And lead he did. He oversaw The Undertaker's WWE Championship victory in 1991 over Hulk Hogan, as well as memorable feuds against Jake Roberts and Yokozuna and others. Bearer was by his side as he went from a feared and despised character in the eyes of the WWE Universe, to a beloved fan favouritie.

Imagine the shock, then, when the above pictured scene played out at SummerSlam. Undertaker was against Mankind in the infamous Boiler Room Brawl. Mankind had become a real thorn in the side of the man from the darkside, so Undertaker undoubtedly needed to keep his closest ally, Bearer, close. It was a real shock when, at the climax of the bout, Bearer stunningly turned on his charge and friend, aiding Mankind to victory before going on to manage him and Vader among others

Paul Bearer and The Undertaker would reunite years later, but this act from 1996 was probably the betrayal of the decade.

#4 THAT Survivor Series...

This was arguably the most controversial moment of the 1990s
This was arguably the most controversial moment of the 1990s

Though the 1990s was packed with incidents, matches, storylines, and Superstars that generated emotion, highs, lows and unforgettable drama, there are few moments that can match this latest image and the story surrounding it for pure controversy.

It's the fall of 1997. Bret Hart is the WWF Champion but, owing to the company's relative financial difficulties, Hart is told that its unlikely they'll be able to meet the demands and commitments of a contract he'd recently penned with them and, as such, he was free to negotiate with and sign for their arch rival, WCW.

While this is the very brief version of this long and sorry saga, the crux of the issue is that this is exactly what Bret went on to do. But, while Hart was Atlanta-bound, Vince had a problem - the Excellence of Execution was still his world champion. What to do, what to do? The circumstances were extremely difficult for all concerned. To get out of the sorry mess with a credible solution, Vince McMahon felt Bret needed to drop the title to Shawn Michaels.

That wouldn't have been an issue, save for the fact that the upcoming event, the Survivor Series, was in Bret's native Canada. In character or not, there was no way, Hart felt, The Hitman would ever be pinned or submit to Michaels in the Great White North. Hart, as the story goes, offered to lose the title to anybody but Michaels, and even offered to willingly vacate the championship the following night on RAW, which was also set to take place in Canada, this time in Ottawa. Michaels vs. Hart was the advertised match, so that's the match that had to happen. Bret expected a non-finish so there would be no winner, no loser, and specifically, no title change. As it turned out, Vince McMahon wasn't prepared to take the risk of Bret keeping his promise and not showing up for his company ever again after that November evening.

The result? The Montreal Screwjob. Bret didn't get his expected non-finish, instead going on to 'submit' to Michaels and lose the WWF Championship. Vince ordered the bell to be rung while Hart was in the Sharpshooter to make it look as if the submission was genuine. It wasn't, and the above photo perfectly encapsulates the emotions of the moment - it's taken just seconds after the bell rings. McMahon is sheepish, Michaels - who knew what was being planned all along - was embarrassed and looking to McMahon for guidance, and Hart was furious.

#3 Shawn loses but wins

Perhaps the most iconic Wrestlemania match of the 1990s?
Perhaps the most iconic Wrestlemania match of the 1990s?

The eighth image of our collection was probably the one you could have bet your house on us including - the iconic shot of Shawn Michaels splashing Razor Ramon from the top of a ten-foot ladder at Wrestlemania X in 1994.

Michaels had legitimately failed a drug test some months earlier and, as the reigning Intercontinental Champion at the time, he had to lose the title. Trying to play up to his cocky, arrogant ways, they cited on screen that the Heartbreak Kid was being stripped of the title and suspended, essentially, for not bothering to defend it often enough.

The result? A vacancy. There was a battle royal on Monday Night Raw as 1993 edged towards its conclusion and, after Rick Martel and Ramon were left standing at the end, they were paired together in a one-on-one match to crown the new champ, a bout that Razor would go on to win.

Soon enough, though, Michaels would be re-instated, and back in action. He cleverly maintained that, as he hadn't actually lost his championship in a legitimate match, he was still the 'true' title holder. He was never officially recognised as such, so the future Hall of Famer would get right under the skin of The Bad Guy, who Shawn claimed to be an imposter champion. The two would trade words and fists, but the end result was the famous Wrestlemania X ladder match in Madison Square Garden.

Razor won it in the end, but few remember that as the take-home moment - for most, the picture above, Michaels soaring through the air, is the fondest memory. It was an unforgettable moment.

#2 Sharpshooting into singles stardom

Bret Hart captures the Intercontinental Championship from Bret Hart
Bret Hart captures the Intercontinental Championship from Bret Hart

Countless millions of fans remember WWE Hall of Famer Bret Hart's career for the stellar matches he helped produce as one of the best singles stars of the 1990s.

From his battles with brother Owen, to a bitter rivalry with Shawn Michaels, to a war on virtually any American he could find by the time the Canadian hero turned heel in 1997, his work on a solo basis was incredible.

It's worth remembering, then, that Hart originally found fame in WWE as a tag team wrestler alongside the late, great Jim 'The Anvil' Neidhart as The Hart Foundation. They were former tag team champions and put on some absolute clinics with the likes of The Rockers. Bret needed, therefore, a way to transition from tag team wrestling into singles stardom once it was decided he was to go it alone. Arguably, the above pictured encounter with Mr. Perfect at SummerSlam in 1991 was the very match that solidified his status as a genuine singles star.

Bret crunched in the Sharpshooter to ensure Perfect gave up, surrendering the Intercontinental Championship in the process. At Madison Square Garden no less, it was the perfect battle between two absolute masters of their craft. Perfect was, well, perfect in so many ways and was the perfect foil for Hart in this match, ensuring the newly-crowned champ was made to look a million dollars.

#1 A star is born

Some images need no caption
Some images need no caption

If you need too much explanation as to what this photo represents, then chances are you're not wholly familiar with the WWF in the 1990s. That's fine - it's exactly why we're here to help! In all seriousness, this photo truly does define an era.

Before Stone Cold Steve Austin hosed down his foes in beer, before he flipped the finger and before he truly hated Vince McMahon on screen, he was the winner of the 1996 King of the Ring.

Having beaten Jake "The Snake" Roberts in a the final, the Texan was crowned King of the Ring, but had exactly zero interest in the pomp and circumstance that had awaited the likes of Owen Hart and Mabel in previous years. Instead, Austin would go on to bury Roberts and, indeed, the rest of the WWE locker room with a blistering promo that included the following immortal line:

You sit there and you thump your Bible, and you say your prayers, and it didn’t get you anywhere. Talk about your psalms, talk about John 3:16…Austin 3:16 says I just whipped your ass!

Indeed, what became known as the 'Austin 3:16' promo helped catapult Austin into the top level of WWE competition, and spurned an entire attitude and culture amongst many WWE fans that has never truly been rivalled.