We all get old, that's just the way things go, but for wrestlers whose professional shelf life is already relatively short, Father Time can creep up on them like a masked, brass knuckle wielding madman. A life of in-ring competition and countless hours spent on the road takes a heavy toll on both mind and body. Add that to the revolving door of newcomers while the sport constantly adapts and evolves and some veterans find themselves suddenly unable to keep up like they once did.
Some legends are timeless, like Lou Thesz or Nick Bockwinkel, seemingly no different during their golden years as they were in their youth. Some, like Edge and Daniel Bryan, were forced to call it quits in the prime of their careers and will always be remembered at their best. Some wrestlers are late bloomers who finally get the chance to shine brightest later in their careers. Others peak quickly and fizzle out over time, holding dearly onto past glories.
The story is different for each individual. While some of the names on our best list were able to age nicely through their careers like a fine wine, those on the other side of the coin either should’ve hung up their boots years earlier or dealt with issues that altered how we perceived them as their careers progressed.
Without further ado, here are the 8 Wrestlers Who Got Better With Age and 8 Who Got Worse.
Click the button below to start this article in quick view
16 Better: The Undertaker
At 51 years old and appearing as rarely as ever, The Undertaker is well past his prime. One could argue since his WrestleMania loss to Brock Lesnar that The Deadman hung on too long and should have retired years ago. While I don’t disagree, he still certainly got better with age as The Phenom was only 25 when he debuted in WWE in 1990.
He’s a tough nut to crack when trying to decipher just when it was that he peaked. I’d guess somewhere between WrestleMania 13 when he won his second World Title and around the time of The Ministry of Darkness.
Regardless of when he actually hit his prime, he’s an enigma who has certainly withstood the test of time. Some of Taker’s best in-ring performances and feuds came later in his career against the likes of CM Punk and Randy Orton, and his two WrestleMania classics against Shawn Michaels are the stuff of legends. Those all came in his 40s, well past what would normally be considered as a wrestler's prime.
15 Worse: Ric Flair
This one’s a little heartbreaking because Ric Flair is the epitome of a professional wrestler and few could hold a candle to him at any point during his career. Flair didn’t win his first world title until he was in his 30s. He spent the next decade stylin’ and profilin’ with the Horsemen, had a successful first WWE run and a triumphant return to WCW. By all accounts, Flair should be one of those who got better with age, but instead, he finds himself on the other side of the coin because he just wouldn’t stop.
Flair made a mockery of his own career while in TNA and on the Hulkamania Australia tour. He should’ve known when enough was enough. Had The Nature Boy actually called it quits when HBK superkicked his career goodbye at WrestleMania XXIV, it would’ve been different. One could’ve looked past his later WCW years and allowed his WWE return and Evolution days to cement his final years.
14 Better: Mick Foley
Raw’s current GM has never been one to stay away from the limelight for too long. Even though, like Ric Flair, he came out of his first retirement to have a couple of feuds and never should have gone on to tarnish his legacy in TNA, Mick Foley blazed a trail in the late 90s and early 00s as the upstart who was never meant to arrive to the big dance but did so after years of truly earning it.
Foley was in his mid-30s when he peaked, hoisting his first WWE Championship above his head and selling out arenas worldwide as one half of The Rock and Sock Connection. His reinvention as the Three Faces of Foley allowed him to become the man in wrestling by simply being himself. It’s allowed Mick to have a long career as a non-wrestling personality who fans still love to see whenever the car crash hits the loud speakers.
13 Worse: The Big Show
For many years now, The Big Show has been that guy who’s just kind of still around. He’s not a jobber by any means, but he’s also not even close to being the draw he was even a decade ago. Show peaked early in WCW by instantly being given their World Title and feuding with Hulk Hogan. He peaked early again in his WWE career with a Championship run and had a great feud with Brock Lesnar in 2002.
Ever since then, however, he’s just kind of lingered around. Show’s upcoming feud with Shaq, as well as his past exploits with guys like Akebono and Floyd Mayweather, profile him to the public as that big pro wrestler guy who the “real people” come in to fight. Makes sense from a business standpoint, I suppose, but as far as a weekly member of the roster, it would’ve been better for his legacy if Show had hit the old dusty trail years ago.
12 Better: JBL
JBL didn’t even arrive to WWE until he was 29 years old. It took him a long time to find his footing as he was bogged down in silly gimmicks like Justin Hawk and Blackjack Bradshaw before finally finding success in the role as Bradshaw of the APA. It wasn’t until he was close to 40 years old that Bradshaw peaked as JBL, one of the most hated and successful heels in WWE history.
After years of being a mid-carder, Bradshaw was finally a main eventer. He had one of the best modern WWE Championship runs in recent memory and became a Triple Crown title winner before officially calling it quits in 2009. Unlike other Superstars who wouldn’t let go of the spotlight, JBL left close enough to his late career prime that his retirement was right on schedule. It’s allowed him an easy transition in becoming a staple of the WWE commentating team since 2012.
11 Worse: Brutus Beefcake
Ed Leslie seemed destined for greatness in his early WWE days as Brutus “The Barber” Beefcake until a parasailing accident put him on the shelf for several years during his prime. Regardless, he was a fan favorite featured in some high profile matches, mostly teaming with best buddy Hulk Hogan. When The Hulkster jumped ship to WCW, so did Brother Bruti and he had a nice heel turn in WCW headlining Starrcade ’94 against Hogan. That’s where it ended, and in all likelihood, Brutus’ career should’ve followed suit then.
Leslie spent the next several years lost in the shuffle as WCW gave him more gimmick changes than you could shake a stick at and one unsuccessful run after another, ending with him as the weird, bearded Disciple of the nWo. At 59 years old, Brutus is still in great shape and actually continues to wrestle every so often on the independent scene, wearing his classic Barber attire and carrying his hedge clippers to the ring.
10 Better: Bob Backlund
Bob Backlund held the WWE Title for nearly five years from 1978 to 1983. He retired in the 80s and would seemingly go down as a successful footnote in wrestling history until oddly returning to the squared circle in 1992 while in his early 40s. It was strange to see such an old school act mix it up with the New Generation at the time as he didn’t really fit in. His days as a main eventer were seemingly well past him. How wrong we were!
Closing in on 50 years old, Backlund reinvented himself as one of the most hated men in wrestling. After setting the Royal Rumble time record in 1993, he played the happy-go-lucky babyface for nearly two years before snapping and becoming a heel in 1994. He had a classic feud with Bret Hart, even beating The Hitman to reclaim the WWE Championship over two decades after his first run.
9 Worse: Scott Hall
Scott Hall’s legal issues and substance abuse battles have been well documented (and exploited) so much over the years that it makes him somewhat an easy target to appear on this list, but it wouldn’t be complete without him. Despite a tremendous run as Razor Ramon, Hall peaked while nearly in his 40s at the onset of the nWo. You’d think hitting your stride at such a late age would qualify him for the better side of things, but Hall’s personal issues dragged him far from the heights they once were shortly thereafter.
It would have been nice for The Bad Guy to have hung up his boots in the early 2000s and gotten the help he needed. His 2002 WWE return was uneventful and every appearance after fell flat as fans could see how far he’d fallen. It’s fantastic to see him healthy again though, thanks to help from DDP, and seeing him inducted into the WWE Hall of Fame in 2014.
8 Better: DDP
Diamond Dallas Page defied the odds down a long road that, like Mick Foley, means everything he got, he earned the hard way. DDP was a manager who didn’t become an official in-ring worker until he was already in his late 30s in WCW. He became a huge fan favorite with legendary feuds against Raven and “Macho Man” Randy Savage and finally peaked by defeating Savage, Hulk Hogan and Ric Flair in a four-way dance for the WCW World Championship in 1999 at the age of 43.
While his stock slid later in his WCW years and he was only able to have a so-so run in the WWE after the WCW purchase, DDP is living proof it’s never too late to achieve your dreams. At 60 years old, his brainchild DDP Yoga is all the rage with former and current WWE Superstars. DDP still makes the odd appearance and looks great, most recently in the Andre the Giant Memorial Battle Royal at WrestleMania 32.
7 Worse: Kane
One could argue that after wrestling as countless gimmicks for six years until finally debuting at 30 years old as Kane, Glenn Jacobs became better with age, and you wouldn’t be wrong. But since being Kane for nearly 20 years and peaking very early on as the character, Kane has seen himself plummeted as a main eventer to just one of the old guys on the roster, much like The Big Show.
Things changed when Kane first removed his mask in 2003. The allure was gone. The mystery vanished. While The Big Red Machine has had some success since, evolving and reinventing his character not unlike his “brother,” The Undertaker, each iteration seems to pale in comparison to the last. He’s nowhere close to the level he was on in his first few years in the WWE. About to turn 50 and nearing the end of his career, it would’ve been nice had Kane called it quits many years closer to his prime.
6 Better: Bret Hart
Bret Hart may be a controversial addition to this side of the list as his WCW run was maligned with injuries and backstage politics and his pseudo-WWE return didn’t see him as anything close to a full time competitor. I would even further the controversy more by saying when you look back on The Hitman’s career to determine when he peaked, it was not at the start of his five-time WWE Championship run, but much earlier, when he held the Intercontinental Title.
Hart’s IC feuds and matches with the likes of The British Bulldog, Mr. Perfect and Shawn Michaels were nothing short of amazing. His World Title feuds again with Michaels and The Undertaker and Stone Cold happened years later when Bret was close to 40. Even before he debuted in WWE in 1985 as one half of The Hart Foundation, Bret had put in a decade at Stampede Wrestling, learning the ropes as he slowly but surely became one of the all-time greats.
5 Worse: Jake Roberts
Like Scott Hall, the downfall of Jake “The Snake” Roberts is a well known, personal tale of substance abuse. Hand-in-hand with the downward spiral that Roberts’ personal life took during the 90s and 2000s, his professional wrestling career plummeted along with him as he seemed to be worse with every appearance.
Jake was an absolute legend in WWE from 1986 to 1992. When he returned to the company in 1996, it was as an aging, out of shape veteran who seemed nothing more than a shell of his once former self, as his life beyond the ring had taken a dark turn for the worse. Jake was never able to recapture that original magic he once had and his infamous independent run during the early 2000s was a sad sight. What’s nice, and again like Scott Hall, is the help he received from DDP. Jake's ability to get control of his issues is spectacular to see.
4 Better: Steve Austin
Steve Austin debuted in 1989 and worked his way through the USWA, WCW and ECW before finally arriving in WWE. After spending nearly a year under the loathed Ringmaster gimmick, WWE finally gave him a chance to shine as he would ultimately stand at the forefront of the wrestling world’s biggest transition in decades. The words Austin 3:16 weren’t uttered until Stone Cold was a seasoned veteran in his early 30s, but he would spend the following decade as arguably the most popular wrestler in WWE history.
Austin’s years as the tough-as-nails Texas Rattlesnake are more or less untouchable these days. They saw him gain more and more popularity while having better and bigger matches during the glory years of the Attitude Era. While neck problems and issues with WWE creative were the two deciding factors that made Stone Cold retire, in retrospect, it was a good thing because he was able to go out on top of the world.
3 Worse: Hulk Hogan
No one is more guilty of refusing to let it go than The Hulkster. Love him or hate him, Hulk Hogan is without question the most popular wrestler of all time and it makes sense why he’d hang on to the glory days for so long. Hogan was still making killer money and holding World Championships well into his 50s, long after his prime had passed.
One could say he peaked with Hulkamania in the 80s and 90s, others could argue it was as Hollywood Hogan in the nWo days. Either way, he without question worsened as the years progressed. The most ironic thing about Hogan is he was never really a good in-ring worker to begin with. Sports entertainer? Absolutely, he was the best, but it’s not like his actual skills worsened over the years. Hogan hasn’t been a full time act for many years, but it’s safe to say old Hulk should’ve hung up the boa a long time ago!
2 Better: Shawn Michaels
Shawn Michaels rocked out in the ring with Marty Jannetty for almost a decade before he finally went solo. He became the WWE Champion in his early 30s, hitting his stride in classics with Bret Hart, The Undertaker and Kevin Nash as the face of the company. While he certainly peaked during the late 90s, Michaels’ decade long return run in the WWE during the 2000s was full of career-defining moments that proved he just got better with age.
HBK’s battles with Triple H, The Undertaker, Chris Jericho and Randy Orton in the later years of his career were epic. While he certainly wasn’t the young, arrogant Heartbreak Kid of the 90s anymore, he was still able to go the distance and put on a show like no other. Now in his 50s and retired, Shawn Michaels is one of the few legends who could return for one last spin and see success that fans would in turn no doubt accept.
1 Worse: Sting
Despite being an icon, Sting has always been the wrestling world’s best example of too little, too late. Not to discredit anything he’s done in his 30-year career, I always thought Sting peaked in his early 30s in WCW long before he donned the Crow gimmick. He returned from the rafters way too late to challenge Hollywood Hogan for the WCW Championship. He joined the nWo long after it was hip and cool. He turned heel so late in his WCW career that nobody cared.
Sting chose to go to TNA where his age truly started to show, but was successful there for the most part. For some reason Sting chose to finally arrive to WWE in 2015 in his late 50s, too little, too late, once again, but in this case, about 20 years too late. While many fans were pumped to see him finally land in WWE, it was not the Sting who should have arrived there and certainly wasn’t when he should have elected to make an appearance.
Leave A Comment
Looking for an AD FREE EXPERIENCE on TheSportster?Get Your Free Access Now!