In the pro wrestling business, timing is everything. You can wrestle 5-star matches in your sleep, possess the microphone skills of a king, have an awesome gimmick and a physique that would make Vince McMahon drool, but if the timing, circumstances and opportunity aren't absolutely perfect, forget about it. A talented wrestler with all the ingredients of a bonafide superstar would fall flat on his face or not be as red-hot as he could’ve been.
Can you imagine Stone Cold Steve Austin’s historic hell-raising, middle-finger-flipping run, which ushered in the Attitude Era, made him a cultural icon, ended the Monday Night War and laid waste to WCW, occurring during the censor-heavy PG era? Oh hell no! Nowadays, he would’ve probably been more Lukewarm than Stone Cold. Can you imagine a beloved and colorful legend like the Ultimate Warrior making his energetic entrance and cutting his intense otherworldly promos being a success—during the Attitude Era? Of course not! The Warrior would’ve been made a laughingstock and most likely would never have gotten a word out over the “WHAT?” chants.
The following list highlights those wrestlers who were just not meant for the era they were featured in. Now while some of these people on the list may have done pretty well for themselves where they were positioned, they likely would’ve done infinitely better in terms of their legacy and career impact had they come up during a different time.
29 15. Boogeyman – Golden Era
The Boogeyman made his WWE debut in late 2005 and to this day makes sporadic appearances typically in a non-wrestling capacity. You can count on Boogeyman for a throwaway segment where he’d break a clock over his head and ooze worms from his mouth for the amusement of no one except Vince McMahon perhaps. Based on a children’s myth, the creepy character didn’t last too long on the main roster largely because he was from a bygone era of cartoony characters and didn’t fit in the landscape at the time.
In the Golden Era, however, he’d fit right in! The Boogeyman would’ve terrified the pre-internet, kayfabe-fed children of the 80s and early 90s as the perfect sinister foil to babyface superheroes like The Undertaker, The Ultimate Warrior and Hulk Hogan. His weaknesses in the ring would be masked in short-form matches in an era where the term “workrate” didn’t hold much weight. And hey, Papa Shango could’ve used a friend.
27 Kofi Kingston – Golden Era/New Generation
Kofi Kingston may be finally adding new layers to his persona in the successful stable The New Day with Big E and Xavier Woods, but before that he was strictly a one-dimensional character. His gimmick was basically, “Jamaican guy that likes to smile a lot and fly around the ring.” Fans appreciated the talent he brought to his matches, but there was not much else Kingston had to offer. In an era where the WWE universe wants more complex personalities, it didn’t work and he languished in the mid-card scene perpetually until The New Day group gave him something to sink his teeth into.
Had the New Day idea not taken off, Kofi very likely may have been stuck in the same go-nowhere rut. However, if Kofi had come up during the Golden Era or the subsequent New Generation area of the early to mid-nineties, he may have had more traction with his boom-clapping and fake Jamaican accent. Those days were ripe with spots for someone of Kofi’s type, with his entire gimmick being that he’s of a particular nationality and leaving it at that. The kids would’ve eaten it up and Kofi would perhaps be in the Hall of Fame by now. Don’t laugh. Koko B. Ware is in there, isn’t he?
25 Natalya – Ruthless Aggression Era
The criminally misused and underrated veteran of the women’s locker room, Natalya should definitely be a bigger deal than she is. She essentially comes from wrestling royalty with her uncle being WWE Hall of Famer Bret “The Hitman” Hart and because of that perk, she trained in the Hart Dungeon. Natalya perhaps has more technical wrestling expertise than the current women’s roster has combined, but alas, she only has one Divas Championship reign to show for it. Even with her skill set and pedigree, she is often lost in the shuffle of the other up and coming divas.
Natalya may have benefited greatly had she started out a few years earlier in the WWE and been a part of the Ruthless aggression era. Natalya’s in-ring skill alone likely would’ve earned her multiple titles reigns at a time when Lita and Trish Stratus were the queens of the squared circle. Lita and Trish are WWE Hall of Fame women now and perhaps with Natalya along with them during that time, they would’ve been the big three female wrestlers at the time.
23 Bad News Brown – Attitude Era
Bad News Brown was one bad mother (shut yo mouth!) in the 80’s. The big African-American brute was a rarity in the WWE at the time and made himself stand out as an angry, take no nonsense superstar who even challenged for the top spot when he went against Hulk Hogan for the WWF Championship.
Unfortunately for Brown, his career with the WWE was a short one and he found himself at odds with management and even cited that his departure was mainly due to Vince McMahon failing on his promise to crown Brown as the first black WWF World Champion.
Brown was wasted by being in the background on the roster and may have been better suited in the Attitude Era where his tough talk and enough rougher style would’ve fared quite well. Bad News Brown as a part of the Nation of Domination? I’m afraid that would’ve been a bit of bad news for the locker room.
21 Sheamus – Golden Era
The Celtic Warrior may have enjoyed a few World Title runs and a Rumble win as the WWE worked to push him on the marquee as a big name but Sheamus, unfortunately, hasn’t caught on as much as the WWE brass would’ve hoped. Perhaps it’s because a person of Sheamus' look and personality would’ve been better suited in an earlier era, the era Sheamus viewed as a child.
Sheamus’ bright white skin and even brighter red hair would’ve fit quite nicely in the Golden Era on top of the fact that he’s a native Irishmen. WWE’s cartoony period of the 80’s with larger than life personalities and international villains may have been the ideal time for Sheamus to carve his name as a force to be reckoned with. Dream matches against the likes of “Macho Man” Randy Savage and Hulk Hogan would’ve also been something to see. How about even the Celtic Warrior versus the Ultimate Warrior?
19 Vader – Golden Era
The hard-hitting mastodon known for being the biggest guy to hit a moonsault off the top rope may have made it his trademark to yell out, “It’s time, it’s time, it’s Vader time!”, but Vader’s time from the tail-end of the New Generation Era to the early beginnings of the Attitude Era was surely a wasted time for such a talented and agile big man.
Vader’s large frame, freaky mask and monstrous style would have made him perfect for the Golden Era. At that time, Vader was in WCW doing his thing and facing off against Sting and Ric Flair. Vader though may have had more value in WWE. At a time where the massive guys the WWE had on the roster were an aging Andre The Giant and a ridiculous joke like Akeem “the African Dream”, the WWE could’ve sorely used Vader as the dragon for heroes like Hulk Hogan and Ultimate Warrior to square up against and slay.
17 R-Truth – New Generation Era
What’s up? That’s a good question actually. What really is up with R-Truth and his terribly outdated hip-hop style? R-Truth started out in WWE in 2000 with a forgettable run as the rapping and breakdancing K-Kwik. 8 years later he would return to the WWE as the rapping and breakdancing R-Truth. A (somewhat) new name but essentially the same exact gimmick, clothing and style he had before. While the gimmick may be kid-friendly, it never translated to much for Truth other than a one-off sniff of a main event PPV match.
R-Truth is like a grandfather in hip-hop culture now. His act was tired when he arrived and it’s definitely beyond stale now. Interestingly enough, Truth would’ve been considered fresh and edgy during the New Generation era and an upgrade over the hip hop caricatures they had in the mid-90s. Also with Tupac being a hip-hop megastar at the time, it would’ve been a prime time to have WWE’s equivalent in R-Truth.
15 Damien Sandow – Golden Era
Oh what could’ve been with the internet’s darling and intellectual savior of the masses Damien Sandow. Sandow’s personality and delivery made him comedy gold during his stint in the WWE and he took whatever WWE management would give to him and make it work like he did as the Miz’s stunt double. Unfortunately, he was relegated to the mid-card for most of his career and a forgotten character during his rather disappointing run.
Sandow’s eccentric personality and snobbish demeanor would have been ideal for the Golden Era of the 80’s and early 90’s. Sandow’s holier than thou attitude and disdain for the fan’s lack of intelligence would’ve made him a hated heel. Imagine him teaming with someone like “The Genius” Lanny Poffo or Mr. Perfect? Sandow could have had a solid career as a part of that roster as a perfect heel for the stars of the time to feud with.
13 Umaga – Golden Era
Umaga’s gimmick was interesting to say the least. Other’s would say it’s borderline racist to Samoans, depicting them as being nothing more than uneducated island savages. Looking back at the Golden Era, the WWE was chock full of gimmicks and personalities which were seen as stereotypical toward various ethnicities, so it wasn’t new territory for WWE or the pro wrestling industry for that matter. The problem with the gimmick comes when you portray a gimmick of a non-English speaking island savage who needs a heavy accented, cigar smoking Cuban to be his mouthpiece—in 2008.
Umaga would have worked a lot more effectively in the Golden Era where Umaga would stand out amongst the array of different villains and evil monsters, each with their distinct characteristics. Umaga’s agility and unorthodox offense would also make him amongst the big monsters who could work a decent match beyond a squash match and have the stamina to go the distance of a main event PPV match.
11 Fandango – Golden Era
Johnny Curtis languished in NXT and then was taken off TV to be repackaged. When news leaked that he was taking dance classes so he could transition into the gimmick of being a ballroom dancer, critics and fans on the internet collectively groaned. How is a ridiculous gimmick like this going to work in modern day WWE? The crazy thing is that it did work, at least initially.
Johnny Curtis went all in with the character making it so he took himself seriously as a dancer even though he didn’t have any discernible skills. However, everyone suddenly remembered that it’s the 2010s so it didn’t stick. The outlandish gimmick is built for the cartoony golden era where it seemed that every character had a different profession outside of being a wrestler.
9 Dean Ambrose – Attitude Era
Ambrose is doing pretty well for himself right now being slotted in the main event and carrying the WWE Championship but seeing a character like Dean Ambrose makes you pine for the days of the Attitude Era because that’s where the “Lunatic Fringe” part of his personality would have really shined. Dean Ambrose is dark, he’s unpredictable, he’s deranged, he’s out there and in the PG era where everything has to be dialed back and toned down, we’re getting a severely sugar coated version of what Ambrose could potentially be if all the red tape was stripped away.
The way Dean Ambrose is depicted on TV would be how Stone Cold Steve Austin would be depicted today. The character would do the best he can, but the edginess just wouldn’t be where it needs to be to really draw the crowd. In the Attitude Era, Ambrose would’ve fit in seamlessly. Ambrose likely would have been a multi-time Hardcore champion, taking on Vince McMahon and having some bloody brawls with Mick Foley. Oh goodness, fire up the Delorean!
7 John Cena – Golden Era
Would Hulk Hogan have been as big as he was if John Cena was coming up in the Rock N’ Wrestling era with the Hulkster? Would CenaMania overshadow Hulkamania? It’s a good question to ponder as Cena’s do gooder heroic character could have slotted into Hogan’s role in the 80’s and early 90’s without a hitch. Cena's a merchandiser’s dream like Hogan was, he has the inspirational promos like Hogan famously did and has the 5 moves of doom like the Hulkster that signal a certain victory.
John Cena’s character is timeless much like the Hulkster’s character and has lasted through multiple generations, remaining on top for so long. While we can never know for sure if Cena would have fared better since he’s been doing phenomenal for 14 years straight and that’s much longer than Hogan was ever on top in WWE. Cena can very well be one of the most versatile wrestler’s ever in WWE history because he’s so adaptable that he could be slotted in any era in WWE’s history and been on top with his “Hustle, Loyalty and Respect” incarnation.
5 Ken Shamrock – Ruthless Aggression Era
“The World’s Most Dangerous Man” was the reverse-Brock Lesnar of the WWE. Ken Shamrock made a name for himself in MMA/UFC then came to the WWE and returned back to MMA. During his time in WWE, he was a staple of the Attitude Era. While he had some success, he never crossed into the upper echelon of the period. The Attitude Era was a very charisma-heavy period where mic skills were key to success, which unfortunately wasn’t Shamrock’s strong suit. Ken played a silent badass that was a ticking time bomb but had to take a back seat to more captivating personalities like DX, Mankind, The Rock and Stone Cold.
Itching to get back into the Octagon, Shamrock would depart from the WWE in 1999 right when his character would’ve potentially been at his most valuable; in an era where catch phrases and crotch chops were gradually replaced with solid wrestling and a sports-like presentation. Shamrock would've seen much better success during the Ruthless Aggression era where his gimmick and personality would've flourished among the other hard-nosed competition at the time. One can only imagine main event feuds with the likes of Kurt Angle, Brock Lesnar, Finlay, Chris Benoit, Eddie Guerrero, RVD, Booker T and the other workhorses of the time.
3 CM Punk – Attitude Era
CM Punk hit his stride in the early 2010’s when the WWE finally gave him an opportunity at being a top guy. It was then that his persona really shined as the cocky, brash and sarcastic “Best in The World”. CM Punk always had to get the last world and one up whomever dared challenge him on the mic be it John Cena or Attitude Era staples like Triple H and the Rock. His verbal jousting skills coupled with his superb in-ring ability proved to the world that he would’ve done great in the Attitude Era amongst the grittiness and edgy material of the time.
Historic events like the pipebomb would’ve been tremendously well received and though CM Punk kept himself off of drugs and alcohol, he definitely wasn’t a role model by any means. Fans still clamor and salivate at the dream contest of CM Punk going one on one with Stone Cold Steve Austin and how epic a rivalry between the two would be. Comments made about Punk from AE era veterans like Austin and the Undertaker stating that Punk is like “One of the boys” from back in those days prove even further that he had what it took to not only survive during the Attitude Era, but succeed.
1 Bray Wyatt – Attitude Era
Bray Wyatt is one of the most memorable original characters the WWE has come up with in the modern era. His entrance, his look, his “family” of followers, his message and his in-ring intricacies have made Wyatt a hit and has made passionate fans angry that Wyatt isn’t used better or positioned more prominently. In the current corporate environment with social media stripping some of the realism away from the show, Bray Wyatt has become a casualty when it comes to truly pushing the envelope with his cult leader character.
The Attitude Era would have certainly served Bray Wyatt the best of any of the wrestlers on this list. Just looking back at how the Undertaker character evolved into a sadistic demonic character who would crucify people, sacrifice them, kidnap them, bury them alive and even attempt to disembowel them, one can imagine the types of terrifying twists and turns Bray Wyatt and his family would have taken had they originated during the Attitude Era when the WWE was more liberal with their content.