Generally speaking, professional athletes are at their physical peak by the time they reach a pretty young age. Professional wrestling is no doubt guilty of this trend, and although times are changing a little bit with the further expansion of WWE thanks to their WWE Network, it’s still pretty hard to find success as a wrestler if you’re over 40. That isn’t always the case, though, as certain wrestlers didn’t even find their niche until they had already crept into middle age, and like a fine wine, they only got better from there.
Plenty of these wrestlers were pretty good or even great when they were younger, and some might argue that their skills deteriorated just a little over time as they do with most people, but our argument is that with wrestling talent being extremely multifaceted, there are far more ways to improve than one, and these wrestlers found dozens of unique ways to better themselves as their careers raged on. In certain cases, a drastic character rehaul was necessary for them to finally find their voice, but these wrestlers were already more than comfortable in the ring, which is one thing experience will always have over youth.
“Middle age” is something too abstract to really define with just a few years, but we’re basically looking at wrestlers who got better in their late 30s or later than they ever were before. Especially considering the average wrestler’s unusually low life expectancy, we feel this more than qualifies for a relatively late time in life to find or rediscover some incredible talents in the ring. All of these performers did, however, so you should keep reading if you want to learn about 15 wrestlers who kept getting better as they reached middle age.
15. Gypsy Joe
Gypsy Joe didn’t just get better as he reached middle age; Gypsy Joe kept improving as a wrestler until well into his time as a senior citizen! Joe was never that famous during his youth, but by the time he was in his 70s, he was getting profiled by WWE and earning his recognition as “the world’s oldest wrestler.” Although not extremely famous in his heyday, Joe was one of the early pioneers of hardcore wrestling, and was compared to major names like The Sheik, Abdullah the Butcher, and Bruiser Brody. He spent decades traveling the world and wrestling in many different countries, but mostly spent his time in Puerto Rico, Japan, and the United States.
The most famous moment of Gypsy Joe’s career didn’t come until he was 69-years- old. Joe was wrestling a more recent proponent of the hardcore style, New Jack. When Joe was in his mid to late 50s, he was still wrestling death matches in Japan against Mr. Pogo, but a decade removed from exploding rings, New Jack proved to be a little bit much for Joe to handle. The two wrestled an extremely stiff and violent match that became a viral hit, although the publicity was mostly negative toward New Jack for legitimately beating a defenseless old man. Nonetheless, Joe took the beating like the pro he was, and continued to do so until he retired at the age of 79. Gypsy Joe passed away in June of 2016.
14. Mark Henry
Mark Henry debuted for WWE in 1996, when he was 24 years old and a recent Olympic athlete in weightlifting. His first 15 years with the company were highly ridiculed, with virtually every storyline he was thrust into more embarrassing than the last. First, Henry dated a transgender woman named Sammy. In today’s society, there’s nothing wrong with that, but it was treated like a big joke in wrestling, which makes it even worse to be involved with it in hindsight. Henry went from being known as “The World’s Strongest Man” to the goofier moniker of “Sexual Chocolate,” and started an infamous relationship with Mae Young. During this period, Henry’s character also revealed a long-term sexual relationship with his own sister, and was videotaped using the restroom for no particular reason.
WWE attempted to take Mark Henry seriously on and off for several years, but he had such an atrocious few years during the height of the Attitude Era that most people completely wrote him off before he was even 30. Everyone knew Henry was still legitimately stronger than almost anyone else imaginable, but his character had almost been irreparably damaged. The only thing that could save it was an incredible career resurgence, which is what happened when he created the “Hall of Pain” in 2011. He won his first World Heavyweight title at Night of Champions that year, when he was 40-years-old.
13. Bret Hart
Bret Hart likes to call himself the best there is, the best there was, and the best there ever will be, and recent interviews with the man would make it seem like he wasn’t just talking about his wrestling character. The boast would therefore imply that Bret was pretty great from day one, and while that’s true in certain respects, we think the overall package with Bret Hart didn’t truly become the best of anything until he was pushing 40. Bret wrestled incredible matches in Canada and Japan while as young as his late 20s, and was already making a name for himself in WWE by the time he was 30. Bret’s first WWE World title came when he was 35, which still isn’t that old, but it still took a few years before Bret truly found his calling.
While The Hitman likes to talk about how great he is nonstop, one thing that even he will admit is the fact that he was never that great at giving interviews. Cutting a promo is arguably the second most important skill a wrestler can have behind actual in-ring talent, and in the cartoon world of WWE, it might even be number one. The fact Bret was never that great at promos made some people push him down from the all-time great status just a little bit, but he finally proved critics wrong as he reached 40 and began his anti-America gimmick that proved he knew how to rock a microphone after all.
12. Bully Ray
WWE fans might not recognize the moniker “Bully Ray,” but there’s not a wrestling fan alive who isn’t familiar with Bubba Ray Dudley. As one half of The Dudley Boyz, Bubba is the significantly more vocal and talented member of perhaps the most dominant tag team in wrestling history. The Dudleyz won the tag team titles of ECW, WCW, WWE, NWA, TNA, and IGWP, and it’s hard to argue they got better as they aged, as their success as a team was pretty immediate and overwhelming. While they may have gotten a bit crisper as they became more experienced, The Dudley Boyz were ready from the word go.
Despite the fact The Dudleyz were one of the best tag team in the business, neither of them seemed to have any luck when the team broke up for the first time in 2002. They would reform and break up several times along the road, but it wouldn’t be until late 2010 that Bubba finally came up with a character that made him a standout star in the singles division. Competing for TNA, Bubba renamed himself Bully Ray and quickly proved he had a serious talent for heel interviews. Two years after rechristening himself, Bully Ray won his first TNA World Heavyweight Championship when he was 41.
Not that anyone on this list necessarily waited until they were older to start getting better, but Batista certainly tried his darndest to be the best wrestler he could from a young age; he just wasn’t given the change. Batista’s first foray into the wrestling business was at the WCW Power Plant, an organization vaguely similar to the WWE Performance Center today, but infinitely less competent in accomplishing any of its goals. Case in point, the Power Plant officials told Batista he’d never succeed as a wrestler, and even with the point we’re trying to make, we think anyone can see why that’s absolute crazy talk.
Nonetheless, Batista trained elsewhere, and eventually debuted with WWE in his mid 30s. Batista was still fairly young by the time of his debut and rise up the card, and the matches he was wrestling weren’t that bad, either. However, Batista was another case of a decent talent with no real character or voice yet, and he finally found that voice as an intensely conceited heel when he attacked Rey Mysterio in 2009. Batista had just turned 40, and unfortunately for wrestling fans, he would take his first hiatus from the business just after he started to get really good.
10. Christopher Daniels
Christopher Daniels isn’t a familiar name to WWE fans, as he only wrestled a handful of matches for the company on minor TV shows, and he never really did anything of note with the company. Fans who follow wrestling in general definitely know about Daniels, and they might also recognize him by Nom de plumes such as Curry Man or Suicide if his own name doesn’t ring a bell. Despite his WWE career being a bust, and a short stint in WCW going much the same, Daniels started to gain some traction in the wrestling world during the early days of NWA: TNA. Daniels won both the TNA X Division and Tag Team titles early on, and a match featuring Daniels, AJ Styles, and Samoa Joe from 2005 is often considered the best match in TNA history.
During the famous Ultimate X match between Daniels and the two future WWE superstars, Joe and AJ were in their mid-20s, while Daniels was already 35. That’s not old to an average person, but it’s later than usual to create a groundbreaking style that puts a promotion on the map. Daniels is even more deserving of this list for the fact it was several years after that he formed the tag team Bad Influence with Kazarian. Many feel both men have done their best work since teaming up, which didn’t happen until Daniels was over 40.
9. Vince McMahon
It’s hard to compare Vince McMahon to some of the other people on this list, since they had completely different ideas in mind when entering the wrestling business. Everyone else we’ve mentioned probably wanted to be a wrestler from a pretty young age, and Vince did, too, but he wasn’t allowed to train for the profession like the others. As the son of a wrestling promoter, and obviously a promoter himself later in life, Vince was told he had to stay separate from his wrestlers and stay out of the ring. Of course, Vince made himself a billionaire by doing things his father told him not to, which is why he wasn’t content to sit from the sidelines, and eventually wrestled his first match when he was 53-years-old.
McMahon had been on WWE television since the 1970s, but his first match took place in April of 1998. Naturally, Vince’s opponent was his eternal nemesis Stone Cold Steve Austin, and although that match was one of the screw jobs Vince is known for, he would prove himself to be decently skilled in the ring later on. Well, at least insofar as a billionaire who never actually trained for the sport is concerned. Vince has the dual distinction of being the oldest WWE World Champion in history and also the oldest World Champion of any kind in history with his reign as ECW Champion, honors achieved at 54 and 61 respectively.
8. Mae Young
They say it’s pretty unlikely to start your career as a wrestler if you’re over the age of 35, but Mae Young proves comments like that are absolute nonsense. Although Mae had been wrestling on the independent scene and for various promotions that were at one point a big deal throughout the 1940s and 50s, she didn’t make her official WWE debut until 1999 when she was 76 years old. A pretty big portion of wrestlers don’t even live that long, and Mae was taking massive bumps off of dangerous heights and through tables, reportedly telling the wrestlers not to go easy on her backstage lest they make the whole thing look fake. Never once did it look like anything less than attempted murder.
The full extent of Mae Young’s influence on wrestling is a little bit sketchy, as reporting on the subject has never been entirely trustworthy, especially not during the era Mae got her start. It’s been claimed she was a Rosie the Riveter type figure in wrestling, inspiring women to get in the ring during World War II, but huge stretches of her career fell into obscurity. Whether or not Mae was necessarily better as a wrestler when she became a senior citizen is debatable, but she was certainly more popular, and able to perform on a level significantly greater than her age would have implied. Of course, it wasn’t all great…
7. Nick Bockwinkel
Nick Bockwinkel is one of the few WWE Hall of Famers who never had a significant run with the company, despite the fact some of his greatest years as a professional wrestler were well within the limits for such a crossover to have happened. Bockwinkel’s father and the legendary Lou Thesz were his primary trainers, and he spent the majority of his career in the American Wrestling Association. While working for that company, he formed a legendary team with Ray Stevens and held the AWA Tag Team titles 3 times. Bock was already in his late 30s when that team started to make him a star, and he was 40 by the time he went solo and won his first AWA World Heavyweight title.
It’s pretty impressive to be in good enough shape to win a World title at 40, but the really amazing thing about Bockwinkel’s feat is that he went on to hold the belt for five years. He briefly lost the belt and won it back, at which point he held it for another year and a half. He would win and lose it twice more, defending his last championship when he was 52-years-old. The most amazing part about Bockwinkel’s reign is that the match quality never faltered, and he continued to wrestle with men half his age at a skill level twice or three times that of the younger men.
6. Bobby Heenan
There aren’t very many true managers left in WWE today, and those that do exist are usually pretty specific cases of a wrestler and a talker pairing up by executive order from day one. It wasn’t always like that, however, as there used to be dozens of managers in WWE, who could easily become the most important part of the show based on how they conducted their business. And no one conducted business quite like Bobby “The Brain” Heenan, who the fans preferred to call by the more insulting epithet “The Weasel.” What fans might not realize is that Heenan himself was a wrestler for many years, and even got in the ring for WWE on the house show circuit in winning efforts long before stuffing him in a Weasel Suit became the way to make a new babyface.
Heenan’s true talents were on the microphone, though, as anybody who has had the pleasure of listening to him talk now knows. It doesn’t matter how good Heenan was or wasn’t in the ring when he was a wrestler, it was when he started to sit behind the commentary booth and give his constant and hilarious thoughts on whatever was happening that he truly shined as a talent. Most of these wrestlers were more impressive in their ability to remain fit in their later years, but leave it to The Brain to weasel his way into this one.
5. Mr. Bob Backlund
Bob Backlund won the WWE World Heavyweight title when he was 28-years-old, and went on to hold that belt for over five years. Obviously, this is near wunderkind levels of success, even for the younger man’s game that is professional wrestling. Backlund was a wrestling machine during this time, working amazing matches against virtually every major heel of the era, and main eventing dozens of successful shows at Madison Square Garden. Backlund’s accomplishments were many and undeniable, but there’s something else undeniable about the era, too: he was extremely boring on interviews, and fans of the time were begging for him to lose the belt less than halfway into his reign. Some would tell you they never liked Bob in the first place.
The problem wasn’t with Backlund; it was with his character. He was the last of the smiling babyface “Golden Boy” era, when a promoter like Vince McMahon, Sr. could make a star by having them win countless matches and tell you they’re a star. Backlund simply seemed like a pretty boring dude who was really good at wrestling, but that finally changed with his career resurgence and comeback in 1992. It still took a few years after that, and in 1994, Backlund finally turned heel and debuted a madman character that made him one of the most hated heels in wrestling. He was fantastic in the role, too, which is why he won his second WWE World Heavyweight title when he was 45.
4. Diamond Dallas Page
WCW regularly booked Diamond Dallas Page as “the world’s oldest rookie,” but he actually got his start with the wrestling business while in his early 30’s, which isn’t old by any stretch of the imagination. However, this start came as a manager, and it wasn’t for almost a decade that Page decided he wanted to try out a career in the ring. While taking this career path in the other direction is fairly common, DDP’s decision had plenty of people laughing at him and questioning his chances of ever becoming a star. Although WCW’s Power Plant was highly flawed, DDP was the one of the few success stories, as he trained there every single day until WCW finally started booking him as a wrestler when he was 35.
DDP’s first few years as a wrestler were spent as a jobber, but he kept training and practicing until he was allowed to win his first title, the WCW Television title, when he was 39. He would ascend to the WCW World Heavyweight title shortly after his 43rd birthday. Diamond Dallas Page was always called a hard working man of the people, and his career trajectory proves that if a person is talented and dedicated enough, age is truly nothing but a number.
3. The Boogeyman
The Boogeyman is the only wrestler on this list who was flat out denied a job by WWE due to his age, only to turn around and get the company to hire him back a few years later, despite the fact he was (obviously) even older than he was a few years before. Boogeyman’s real name is Marty Wright, and his first exposure in WWE came on the original version of Tough Enough. Even hardcore fans of the show might not remember him, though, as he was cut from the competition very early on for lying about his age—Wright was 40, and the cut-off for Tough Enough was 35.
Although he was too old to even be allowed to try and get a WWE contract through the means he had originally intended, the company can often be wildly unpredictable, and offered Wright an invitation to train with them anyway. He contrived the character of The Boogeyman, and made his WWE debut on SmackDown in October of 2005, when he was 41. The Boogeyman only lasted four years with WWE, in part due to his slightly advanced age, but they were still four years far more successful than anybody would have guessed for a guy told he was too old from day one.
2. The Undertaker
The Undertaker is also called “The Phenom of WWE,” and there isn’t a wrestling fan alive who couldn’t make some sort of argument for The Dead Man as one of the greatest of all time. Regardless of how one feels about the cartoonish WWE style of sports entertainment, The Undertaker stands as a cut above the rest, with a brilliant gimmick matched with the perfect performer who has been able to create over 25 years of professional wrestling history. The Undertaker was poised for the stuff of legend from the start, but most fans would agree that he didn’t start wrestling truly great matches until well into that tenure.
The Undertaker debuted as such in 1990, when he was 25, and had been wrestling in WCW and Memphis a few years prior to that. When he transitioned from Mean Mark Callous into The Undertaker, his matches were extremely slow and plodding, but it’s not really fair to judge him for that, since he was playing a literal zombie. When paired with the right opponent, Undertaker could create an absolute classic, but he himself was more spark than substance in the ring. Especially during the Attitude Era and the following American Badass gimmicks, certain fans always felt The Undertaker’s mystique dipped just a little with his bland and repetitive matches. That ceased somewhere around 2007, when he decided not only was “The Streak” going to sell WrestleMania, but his matches would steal the show every year. To be fair, though, The Undertaker had some help in that regard…
1. Shawn Michaels
There are countless wrestling fans, including the people who compile WWE’s DVD releases, who feel that “The Heartbreak Kid” Shawn Michaels is the greatest professional wrestling superstar of all time. His charisma and talent inside the ring are truly second to none, and this has been true almost since the day he debuted in the mid 1980’s after being trained by Jose Lothario. Maybe it wasn’t natural talent from day one, but Michaels was already showing boundless charisma when he teamed with Marty Jannetty as The Rockers, and he was well on his way into wrestling history when he won his first WWE Intercontinental title in his late 20s. The veritable “boyhood dream” came true and Michaels won the WWE World Heavyweight title when he was 30, but then tragedy struck, and he seemingly was forced to retire at 35 due to a serious back injury.
As most wrestling fans know, that luckily wasn’t the case, and Michaels had a career revival beginning at age 37 that plenty of critics feel was even better than his 15 years prior to getting hurt. Regardless of his actions in the ring, Michaels was also definitely a better person during this period of his life, as he no longer was blatantly hurtful to his co-workers, and seemed willing to be part of the bigger WWE program instead of solely being interested in himself. On top of that, his match quality remained amazing, and it wouldn’t be a stretch to call HBK’s retirement match against The Undertaker at WrestleMania XXVI one of the greatest of all time.
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