WWE Royal Rumble winners: Where are they now? (1988-1999)

"Winning the Royal Rumble" is one of those career achievements in WWE that's as prestigious as winning an actual championship. After all, only 26 men (27 if you want to count Braun Strowman winning the "Greatest Royal Rumble" in Saudi Arabia, although we advise against it) and three women can claim such an accomplishment. So, it's a bit of an exclusive club. Even the records held within the event (longest time spent in the match, number of eliminations, etc.) are sources of pride.

Most of the Superstars who have won the Royal Rumble match have gone on to have some pretty great - even Hall of Fame worthy - careers. Others, well... haven't. But all of them deserve a place in history.

In this piece, we're going to look at the careers and current whereabouts of the winners of the Royal Rumble Match from the very first year, 1988, until the final one of the 20th century, 1999. We'll have another piece about the winners from 2000-2009 shortly after. We might even do 2010-2020, although that one should be fairly easy to write.

So, let's get to the very first entry, and the very first Royal Rumble winner ever.... TOUGH GUY! HOOOOOOOO!

10. Royal Rumble 1988 - 'Hacksaw' Jim Duggan

The Pride of Gens Falls, NY, "Hacksaw" Jim Duggan is one of the most recognizable pro wrestlers of his era. For starters, he's one of three wrestlers in the history of the business to get a single word - "Hoooooo!" - over as a crowd-chantable catchphrase (if you can guess the other two, list them in the comments).

In 1988, an exhausted Duggan won the innaugural Rumble match (aired on the USA Network), when he pulled down the top rope to eliminate a charging One Man Gang.

Like a lot of his contemporaries, Duggan continues to wrestle sporadically on the independent scene. In 2014, he was a cast member on the WWE Network reality show 'Legends House', along with Roddy Piper, Gene Okerlund, and Pat Patterson. While he was most recently in the hospital for a heart condition, as of this writing, he is alive and well and happy, living with his wife Debra in South Carolina.

9. Royal Rumble 1989 - Big John Studd

It's appropriate that a "giant" won an early Royal Rumble.

John Minton was everything his ring name said. He was big, he was a stud, and his name was John. He was also one of the most underrated performers of his era.

(Thank you to Wrestling Bios on YouTube)

While Studd had a prolific career in the territories and the AWA, as well as the early years of the WWF - back when they had an extra W in their name - his first big moment came during his feud with Andre the Giant, when he and the Giant fought in a "$10,000 Bodyslam Challenge" at the very first WrestleMania. Standing at 6'10" and weighing in a just over 350lbs., Studd was hardly dwarfed by the legendary Andre. However, Andre prevailed and their feud continued.

In 1986, Studd retired from wrestling and the WWF. That would last for two years, when Studd announced his return on a "Brother Love Show" segment on WWF Superstars. While Studd's former manager, Bobby "The Brain" Heenan, was elated to see his former charge back in action, Studd wanted nothing to do with The Weasel - who was also now the manager of Studd's former rival, Andre.

So, in 1989 and as a babyface for the first time in his career, Studd won the Royal Rumble by eliminating Andre's cohort, "The Million Dollar Man" Ted Dibiase - then fighting off an attack by Virgil.

The Royal Rumble win would, sadly, be the major highlight of Studd's career. After a diagnosis in 1993, John Minton succumbed to a long battle with liver cancer on March 20, 1995. He was 47 years old.

8. Royal Rumble 1990 & 1991 - Hulk Hogan

When Hulk Hogan entered his first Royal Rumble match, he was in the midst of his second WWF Championship reign - having won the title back at WrestleMania V. He would go on to win that Rumble but, more notably, it set up his program with The Ultimate Warrior that would lead to their WrestleMania VI main event.

The following year, Hogan was without his championship - having lost it in that bout with the Warrior - entered the Royal Rumble match and, for the second year in a row, won. Coincidentally (well, not really), the Ultimate Warrior had lost that same title to Sgt. Slaughter - thanks to interference from "Macho King" Randy Savage. Hogan would go on to face - and defeat - Slaughter for the belt at WrestleMania VII.

Following WrestleMania VII, Hogan seemingly vanished off the face of the Earth.

Seriously, though, you all know what Hogan's career was like after that. Nowadays, Hulk has mostly kept a low profile - probably due to the fallout of his sex tape/saying racist stuff scandal from a few years ago. Hogan has appeared ata number of WWE events over the years - most recently alongside Jimmy Hart at the latest Raw Legends Night.

7. Royal Rumble 1992 - "Nature Boy" Ric Flair

The fact that we live in a world where 'Nature Boy" Ric Flair not only won a Royal Rumble match - but won the WWF Championship because of it - means that we somehow live in a just world.

Ric Flair left WCW back in 1991 after decades of being the face of the NWA/Jim Crockett Promotions organization. Following the purchase of the organization by Ted Turner, Jim Herd was put in charge of the promotion. Jim Herd used to run Pizza Hut. Jim Herd wanted Ric Flair to shave his head and call himself 'Spartacus'.

So, Ric Flair told Jim Herd to stick it and then joined the WWF. And then Ric Flair won the 1992 Royal Rumble and became WWF Champion.

Ric Flair won the Royal Rumble - and the title - in 1992. And he still managed to be The Man for years afterwards. He's Ric G'D'd Flair. Nowadays, he's involved in the career of his daughter... someone you might have heard of by the name of Charlotte.

Over the past half decade, Flair has gone through a lot - medical scares, marriages, family tragedies, bad suits. These days, he's involved in an angle between Charlotte and Lacey Evans, where's he's... well... being Ric Flair with Evans.

Granted, despite the really crummy booking The Queen has had to deal with over the years, and despite the fact that 2020 has been a garbage bag of years set on fire - it's still something to behold.

6. Royal Rumble 1993 - Yokozuna

Following the Royal Rumble match where Ric Flair won the world championship, it was determined that there needed to be something to make the Royal Rumble relevant as far as the current stories being told went. So, it was decided that every year, the winner of the Royal Rumble match would go on to wrestle for the WWF Championship at that year's WrestleMania.

It's kind of like how Major League Baseball decided to award home field advantage of the World Series to the league that won the All-Star Game. Otherwise, those All Star Games would go on forever because none of the players gave a tookus about it. Before 1992, the Royal Rumble was kind of like the MLB All-Star Game of wrestling matches.

Also in 1993, WWF presented their newest Final Level Big Boss Bad Guy, Yokozuna. At the time, the relations between Japan and the United States were a bit frosty, as the economy in the US wasn't so great and the economy in Japan was awesome and how dare they!? So, WWF found a Samoan guy who looked to be the size of a Sumo wrestler, said he was from Japan, and made him a bad guy.

Like a lot of stupid ideas the WWF came up with at the time... it worked...

Yokozuna would go on to defeat Bret Hart for the WWF Championship at WrestleMania IX - and then immediately lose it to Hulk Hogan right afterwards. Of course, the Hulk Hogan reign didn't last very long and Yokozuna would eventually get the title back, and Hogan would end up on Thunder In Paradise before ending up in WCW.

And we all know how that ended.

Unfortunately, Rodney Anoaʻi - after a career that saw him also win Tag Team gold with Owen Hart and even a short-lived face turn that saw his manager, Mr. Fuji, wave the American flag as opposed to the Japanese one (and is something I still consider one of the coolest things ever) - would pass away in England in 2000. He would go on to posthumously be inducted into the WWE Hall of Fame.

5. & 4. Royal Rumble 1994 - Bret "Hitman" Hart and Lex Luger

1993 and 1994 were a couple of weird years for the World Wrestling Federation, even outside of the Royal Rumble. Hulk Hogan had come back, won the WWF Championship in the dumbest way possible, lost it also in the dumbest way possible, and then left. So, we were back where we started, with Yokozuna WWF champion and Bret Hart seeking revenge.

Meanwhile, WWF's other top draw, Lex Luger, was still being groomed to be the second coming of Hulk Hogan - especially because Hogan made it clear he was done with pro wrestling. Lex would have a high profile world title match with Yokozuna at the 1993 SummerSlam, which he would win... by countout. So, despite the gigantic, put-him-on-your-shoulders celebration the babyfaces of WWF held for him afterwards, Luger wasn't the champ.

Flash forward. So, the 1994 Royal Rumble ended with Bret Hart and Lex Luger as the last two men in the ring and both of them - in a move that sill boggles the mind in the timing and precision is had to have taken - both eliminated each other at the same time.

And thus we have the first and only time two men were named winner of the Royal Rumble.

Well, there was a convoluted solution at WrestleMania X, which is way too long to get into right now, but it ended with Hart winning the title and Luger congratulating him.

Coincidentally enough, both Luger and Hart would end up in WCW together years after, and renew this rivarly, although by that point, nobody really cared.

Lex has been through a lot in the years since then, including a lot of personal and emotional trauma - way more than we need to go into now - but these days, he's working with WWE to bolster their wellness and nutrition programs and seems pretty at peace these days.

Bret Hart has also been through a lot following that Royal Rumble, but nowadays he's a two-time WWE Hall of Famer and seems to be enjoying retired life quite a bit.

3. Royal Rumble 1995 & 1996 - Shawn Michaels

Three years before winning his first Royal Rumble, Shawn Michaels watched his hero, Ric Flair, enter the match at number three... and win.

Michaels, being Michaels, pretty much said "hold my beer." I mean, he may have said that, as he was drinking beer in those days.

In 1995, Michaels won his first of two back to back Royal Rumble matches at entry number one. It was, at that point, the most impressive Rumble match performance ever. Even the way he won caused WWE to emphasize the "both feet must hit the ground" rule from then on.

That win earned him a WrestleMania XI WWE Championship match against his former bodyguard Diesel. While the next year he won less impressively (as if winning the Royal Rumble is ever not impressive), it led to his legendary Ironmatch match against Bret Hart for the championship at the following WrestleMania.

Following the kind of career - personally and professionally - that one could make a movie about, Michaels retired from competition after WrestleMania XXVI in a Streak vs Career match against The Undertaker. He's only made one appearance as a competitor since then that we're not going to talk about nope I am not you can't make me, but still has shown up in plenty of non-wrestling roles over the years.

Currently, he's working with Triple H in NXT as a trainer.

2. Royal Rumble 1997 & 1998 - Stone Cold Steve Austin

Stone Cold Steve Austin and his imaginary watch

Even with the Royal Rumble, what can we say about Stone Cold Steve Austin? When Vince McMahon inducted him into the WWE Hall of Fame, he called him "the greatest WWE Superstar of all time" and it's hard to argue with that. After all, who's going to argue with Vince? Other than Stone Cold, anyway

Considering he's got three Royal Rumble wins under his belt, there's not a lot we need to go into about each Royal Rumble win. Especially considering how long this piece already is. So, here's some videos:

Stone Cold Steve Austin is currently living the good life, taking the ocassional movie roles (he was in The Expendables, don'tchaknow?) and hosting his really freakin' good Steve Austin Show podcast.

WWE keeps him busy, as well, with his Broken Skull Sessions interview show on the WWE Network. His interviews with The Undertaker last year were a big component of WWE's celebration of his career following his retirement.

1. Royal Rumble 1999 - Mr. McMahon

That's right. Vince McMahon. He won the Royal Rumble.

This was at the height of the McMahon/Steve Austin feud during what I suppose some people call the "Attitude Era." McMahon had put a "bounty" on the head of Austin, with a heap of cash going to whomever could eliminate the Texas Rattlesnake and prevent him from going to WrestleMania. He even entered it himself to help ensure it wouldn't happen.

By the end of the match, it was just Austin and McMahon and... well... the video above will tell you exactly what happened.

McMahon would give up his title shot, as the current champion at the time was his "Corporate Champion" The Rock. Of course, Austin would still go on to challenge Rock for the title at that year's WrestleMania, anyway, but it was a good plan while it lasted.

Nobody has heard from him since.

Just kidding. If I had to guess, he's probably backstage at the ThunderDome, getting things ready for this year's Royal Rumble. Even in his 70s, Vince McMahon doesn't take a day off.

Please, Vince. Take a day off. Go to a spa or something.

A WWE Hall of Famer called out AEW fans HERE