Coolness is a quality that almost every human strives for. For some, coolness comes effortlessly. For others, being cool can be as unnatural as walking on their hands. In pro wrestling, coolness can be a very valuable weapon in a performer’s arsenal and can often lead to success.
Over the years, guys like Razor Ramon and Rob Van Dam got over huge with fans mostly by being cool. Not every pro wrestler is as blessed as “The Bad Guy” and RVD though. On the contrary, some performers across WWE and WCW have found coolness to be extremely elusive, no matter how hard they tried to attain it.
10 Dude Love
Pro wrestling may never see a performer as gifted and versatile as Mick Foley ever again. That being said, one of Foley’s three alter egos was a bit cheesy. In 1997, Foley’s Mankind persona would take a back seat to Dude Love. Where Foley’s other two personas, Mankind and Cactus Jack, were violent and deranged, Dude Love fancied himself “The Hippest Cat in the Land.”
Unfortunately for Dude, his perception was far from reality. To be fair though, the character was designed to be lovable but uncool. Despite the lack of badass appeal, Dude Love was a nice change-up from Foley’s two other faces.
9 “Macho Man” Randy Savage
At some point, every athlete learns that Father Time is undefeated. In pro wrestling, that reality can often be compounded by the fact that performers have to worry about maintaining their look as well as their talent. For most of his career, “Macho Man” Randy Savage had both of those departments on lock.
Unfortunately, by 1999, Savage was beginning to lose a step in the ring. Furthermore, his iconic look was beginning to seem dated and old. This led to Savage regrettably revamping his character. The updated “Macho Man” tried his best to be hip and cool, but it honestly seemed forced. The man who had been effortlessly cool for so long became the old guy in the club. Luckily, this is the least remembered version of Savage.
8 Shane McMahon
Stepping out of any parent’s shadow can be a tall task for a son or daughter. Now imagine if your father was the most successful sports entertainment promoter of all time. That’s quite a long shadow to try and escape. That’s the scenario a young Shane McMahon found himself in during the mid and late 90s.
In 1998, Shane became an on-screen regular in WWE. In order to live up to the McMahon name, Shane would turn his personality up to 100. At times, Shane’s attempts to be cool could come off as obnoxious. Admittedly though, that was kind of his character at the time. Eventually, Shane would tone it down just a hair and become effortlessly cool.
7 Enzo Amore
Just like a young Shane McMahon, Enzo Amore loved to walk the fine line between coolness and obnoxiousness. During the mid 2010s, Enzo was part of an insanely popular tag team, alongside Big Cass. The combination of Enzo and Cass was red-hot at one point and reminded many fans of the golden days of The New Age Outlaws.
Enzo was certainly a good talker, blessed with the gift of gab. Unfortunately, he rarely knew when to stop talking. On many occasions, Enzo would say something extremely cool and then keep running his mouth until it became obnoxious. His mouth ultimately earned him a lot of backstage heat and is probably the main reason he’s no longer in WWE.
6 The Disciple
The header on this entry says “The Disciple” but you can honestly slide any of Ed Leslie’s WCW personas on there. As Brutus “The Barber” Beefcake in WWE, Brutus could often be over the top but in an enjoyable way. When Brutus followed his good friend Hulk Hogan to WCW though, his on-screen characters would take a turn for the worse.
“The Butcher” and “The Zodiac” were both terrible gimmicks but at least they weren’t obnoxious. “The Bootyman” on the other hand reeked of desperation. Then, when Leslie switched to The Disciple, the gimmick just screamed “trying way too hard.” Fans knew Leslie was far from a legitimate biker or a badass so the gimmick and the attempt at coolness didn’t seem genuine.
The wrestling business can chew up and spit out even the most mentally tough performers. Now, imagine what it’ll do to a mentally fragile performer. Unfortunately, Kanyon found out firsthand just how vicious and unfair the business could be. In 1997, Kanyon broke into WCW as Mortis. Eventually, though, he’d transition into a less gimmicky character.
That didn’t really get him over with fans though. Heading into the new millennium, Kanyon would attempt to turn the volume way up on his persona. The results weren’t good though. While “Who’s Better Than Kanyon?” was a great catchphrase, the character that came along with it never caught on with fans. No matter how hard he tried. Unfortunately, the wrestling business would never reward Kanyon with the success he deserved.
4 Hollywood Hogan
Two things in pro wrestling can be true simultaneously. Hollywood Hogan’s coolness, or lack thereof is a great example of this. It’s easy for many fans to look back and view 1996 through rose-colored lenses. Yes, Hulk Hogan turning heel revolutionized the wrestling industry and birthed the most influential and important group ever, The nWo. However, with the benefit of hindsight, it becomes obvious that Hollywood Hogan wasn’t naturally cool.
What many fans love to forget or perhaps just chose to overlook is that before linking up with Scott Hall and Kevin Nash, Hogan’s coolness was at an all-time low. So, when looking back at Hogan with that in mind, it becomes a lot more obvious that Hollywood Hogan was just piggybacking off of The Outsiders’ natural coolness. Anyone needing further proof just needs to look at how uncool Hogan got when Hall and Nash weren’t by his side.
3 Jeff Jarrett
This entry should come as no surprise to anyone. Young fans today will likely never understand just how uncool and easy to hate Jeff Jarrett’s character was during the 90s. Sure, TNA Jarrett could generate a lot of heat too, but that was more traditional pro wrestling heat that many top heels strive for. Jarrett’s 90s heat was a different story.
At the time, Jarrett was trying so hard to get over with fans that he grasped at every straw possible. He wore flashy, over-the-top attire. He was a shameless self-promoter. Perhaps worst of all, he thought it was cool to strut like Ric Flair. It all came off as forced and fans rejected Jarrett for it. He was arguably the most hated wrestling character of the 90s.
2 Vinnie Vegas
During the late 80s and early 90s, Americans were obsessed with The Mafia. Movies like The Godfather, Goodfellas, and Casino only added fuel to that fire. Surprisingly, WWE never made any blatant attempts to piggyback off of that popularity during that time. WCW took a stab at it though when they introduced the Vinnie Vegas character in 1992.
To a degree, the character seems to have been a slight parody of mobsters. Either that or Kevin Nash just tried way too hard to seem like a cool mobster. Over the years many have compared Vinnie Vegas to Steve Martin’s character in My Blue Heaven. Regardless, the wrestling world is lucky that Nash didn’t do a good job as a mobster or else he might’ve never become Diesel.
1 Diamond Dallas Page
If there was a physical copy of a wrestling thesaurus, Diamond Dallas Page’s picture would be next to the term “trying too hard.” During the early 90s, Page was transitioning from a managerial role into an in-ring performer. Let’s just say his transition had some growing pains. In an attempt to seem cool, Page threw a bunch of ideas up against the wall in hopes that one would stick.
He had colorful attire, eye-catching entrance vests, jewelry, and wacky glasses, and came out with a cigar in his mouth. Alone, any one of those things can enhance a performer’s look and possibly add some cool points. Page overdid it though and fans could tell. Luckily, DDP would eventually find the version of his character that worked for him, and he’d ride that persona to the top of WCW.