The WWE has gone through a lot of changes in the last twenty years or so. Wrestlers and performers have entered the WWE and many wrestlers and performers have exited, some with more fanfare than others.

While the company has been alive and kicking much longer, since 1990, the World Wrestling Federation or World Wrestling Entertainment has been trying to hit home runs with characters that are often a bit out of the box. More often than not, things don't pan out. For every Kane or The Undertaker, there is a Bastion Booger or Damien DeMento. In fact, there are so many failures, it became an interesting exercise to look back at the last twenty-eight years to determine the biggest flops the company ever produced.

In determining the worst wrestler in each year, we used the following criteria. First, wrestlers had to have made at least 75 appearances for the company in that calendar year. Anything less and we didn't really consider them more than a per appearance jobber who was never really meant to become a success.

Second, we could not use the same wrestler twice. While some gimmicks were so bad they deserved consideration for making the list more than once, we wanted to share the wealth and didn't want to leave anyone out.

Third, we didn't specify what made them the worst and as such, there are a variety of reasons a wrestler may have made the list. From a terrible gimmick to a performer going off the deep end and ruining their own career, it all counted. Sometimes it was their lack of in-ring skill and other times it was the company not knowing what to do with a very talented performer.

Make your way down our list from 1990 to today. See how many names you recognize and if you'd have selected someone else.

28 28. Black Bart (1990)

Black Bart during an interview

Black Bart was a well-traveled veteran in the industry having wrestled in a number of promotions before joining the WWE in 1990. His stay in the World Wrestling Federation lasted just over a year and he was mostly used as an enhancement talent. While Bart scored victories over fellow jobbers like Jim Powers, and Pez Whatley, it was about the most he could muster. Having appeared over 130 times in 1990, the highlight of his career was when he teamed with Mark Ming for a shot at the WWF World Tag Team Titles and wrestle the then-champions, Demolition. Needless to say, Bart and his partner lost.

After he fizzled out of the WWE, Harris wrestled in the independents for the rest of his career before retiring in 2002. One thing to note is that he became a trainer and trained Necro Butcher who was featured in the 2008 film The Wrestler.

27 27. The Mountie (1991)

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The Mountie (Jacques Rougeau) had a run of just over a year, but only a few months where he was actually relevant. He had three claims to fame. First, he was the Intercontinental Champion for all of two days. He was used to place-hold the title while Bret Hart was negotiating a new contract. Second, he feuded with The Big Boss Man in a Jailhouse Match (which he lost) and had to spend the night in prison. Finally, and likely worst of all, he could only use his gimmick part time.

The character was the subject of litigation in Canada, leading to a lack of being able to use the character in Canada (where The Mountie was from). So, in a place where his gimmick would have had the biggest effect, he couldn't use it. He went by his real name and didn't wear the uniform.  The closest he could get was a red shirt, black pants, and boots. The announcers actually had to publicly announce that Rougeau did not represent Canada.

26 26. Nailz (1992)

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Another character created to feud with The Big Boss Man, the career of the character known as Nailz was short-lived and turbulent. Meant to portray an escaped convict who's sole motivation was getting back at the Boss Man for putting him behind bars, Nailz had an intimidating look, but he also had a real life temper. His time with the WWE ended abruptly when after feeling slighted regarding his pay, he stormed into Vince McMahon's office, asked the Berzerker to hold the door and proceeded to physically assault McMahon over the money he thought he was due.

He was immediately released and never heard from in the WWE again. He was part of steroid investigation that saw McMahon go on trial, but because Nailz was so hell-bent on getting McMahon locked up, he lied on the stand and the case was thrown out.

25 25. Damien DeMento (1993)

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If I asked if you knew the name Phil Theis or Mondo Kleen, would you have any idea who I was talking about? If I asked you if you'd ever heard the name Damien DeMento would you? A lot wouldn't, but those who would know DeMento as the man who was featured in the main event on the first ever episode of RAW. His opponent was The Undertaker.

When he was signed in 1992 and presented as Mondo Kleen, he lost clean (pun intended) to Jeff Jarrett.  Soon after, he was completely repackaged. He became a wanderer who officially hailed from "the outer reaches of your mind."  DeMento didn't even get a feel year's worth of employment under his belt as he left the WWF in the latter part of 1993 over a dispute regarding the company's drug testing policies.

24 24. Bastion Booger (1994)

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After getting in trouble with the Roman Catholic Church over his Friar Ferguson gimmick, Mike Shaw was repackaged as an unkempt, slovenly and gluttonous slob who wrestled in dirty and too-tight, gear. It was all meant to disgust the audience and it worked.

His first feud was with Virgil (that should tell you all you need to know about how the company viewed him) and he lost. His only company high-point was in beating Owen Hart before Owen's big main-event push. Eventually, Booger feuded with Bam Bam Bigelow and then no-showed the 1994 Royal Rumble. He was let go in August of that same year.

The only time the WWE ever saw him again was in 2007 when he was brought back for a special appearance on RAW, playing the rumored father of fellow slob Big Dick Johnson.

23 23. Rad Radford (1995)

Louie Spicolli actually went on to have a decent tenure in ECW, which got him a job in WCW as a lackey for Scott Hall. In the WWE however, he was known as Rad Radford. The WWE and Radford tried to play off the changing grunge rock scene that was prevalent at that time and Radford was portrayed as a grunge rocker who claimed to be Courtney Love's ex.

In 1996, Spicolli was found unconscious by a neighbor after overdosing and having suffered a seizure. He recovered but was released seeing as the WWE was still very cautious about their image in the mainstream media when it came to drugs. Unfortunately, in 1998, Spicolli passed away in his sleep after overdosing on the same drugs that took him out of action a few years earlier.

22 22. Aldo Montoya (1996)

Aldo Montoya dropkick

Most people would later come to know Aldo Montoya as Justin Credible, but before winning the ECW Championship or making his return to the WWE in an ECW revival mode, Credible was the "Portuguese Man O' War". Montoya and Credible's real name is Peter Joseph Polaco and he eventually became friends with the Kliq, which probably added a couple years to his first contract, but he spent most of his days trying to get over with a jockstrap looking mask on his face.

In 1995, it looked like the WWE was going to try and do something with Montoya, having him feud with Intercontinental Champion Jeff Jarrett but that never turned into much and by 1997, he'd asked for his release from the company. He was sent to ECW as part of the talent exchange and had a much better career there.

21 21. Rockabilly (1997)

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At the start of 1997, The Honky Tonk Man decided he needed a protege. It was originally supposed to be the Disco Inferno, but when he resigned in WCW, the WWE turned to tag team wrestler Billy Gunn to take on the role. He had a short feud with Road Dogg Jesse James, but the two quickly realized their singles careers were headed nowhere fast. James suggested the two form a tag team and they did, creating the New Age Outlaws and eventually joining DX.

Billy Gunn was never a terrible worker and he had some very successful characters in the WWE, but Rockabilly is one that he's probably stuck in the 'do not talk about' vault. It was not going to work and mainly because Gunn was not nearly as entertaining in a heel role as The Honky Tonk Man was.

20 20. Marc Mero (1998)

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Marc Mero had come over to the WWE in 1996 and was one of the biggest signings in the WWE at that time. He was the first ever wrestler to be given a guaranteed contract by the company and for that reason he's on this list. You see, by 1998, it was obvious that Mero was never going to have the kind of success he saw in WCW and as such the WWE was stuck with his contract. Sable, his wife at the time, was becoming a bigger star than Mero was and after getting repackaged as "Marvelous Marc Mero", a boxer turned wrestler, his career in the WWE was on a rapid decline. He was gone from the WWE by 1999. At the time, Mero had three years remaining on his contract, with a guaranteed salary of $350,000. Mero was not the best way for the company to start handing out guaranteed contracts.

19 19. Prince Albert (1999)

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Matt Bloom is now a trainer in NXT with the WWE. As a wrestler, he managed to carve out a decent career, but he went through some pretty awful gimmicks. The worst was probably being named after a pen!$ piercing.

Bloom debuted on WWF television on the April 11, 1999 episode of Sunday Night Heat and was dubbed Prince Albert, the personal tattooist of Droz. Together they formed a short-lived trio with Key. Droz and Albert continued to team together until Droz was paralyzed in October 1999, at which point Albert became the protege of the Big Bossman.

The timing character never took off and it's not really surprising. With that name, I don't the WWE even took him seriously. Bloom would have made our list again in 2013 as Tensai, but our rules suggest we had to pick someone else.

18 18. Essa Rios (2000)

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He first debuted in the WWE as Augila. At that time he was part of the WWE's Lightweight Division. At one time he did win the Lightweight Title but lost it quickly after to Dean Malenko. When he re-debuted as Essa Rios, he didn't fare nearly as well.

Managed by Lita she actually gained more attention than he did for repeating his moves after his matches had ended. When he attacked her for losing a match, the Hardy's came in and saved her which led to their connection. Eventually, he was completely forgotten about and started taking bookings in Japan. Essa Rios was both a result of a failed Lightweight Division and people caring less about the guy who was with Lita because Lita was far more over with the audience.

17 17. Lance Storm (2001)

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If I could be serious for a moment...

Lance Storm was an awesome wrestler, he just didn't have much of a personality and when he came over to the WWE from WCW, he was touted as one of the big stars to defect, which of course he wasn't. Names like Kevin Nash, Scott Hall, Sting and Goldberg all sat at home and Storm was meant to be a replacement in a situation that was doomed from the start.

Lance Storm was one of the better technical wrestlers in the WWE, but because the WWE didn't know what to do with him and they completely botched the whole Invasion angle, Storm may go down as one of the most underutilized talents in WWE history. He's still an active wrestling teacher and supporter but his WWE run was not pretty.

16 16. Christopher Nowinski (2002)

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Chris Nowinski makes our list, but technically he breaks one of our rules. We said 75 appearances qualify a wrestler, but Nowinski had 69 and part of the reason he didn't have more was due to concussions. In fact, Nowinski ended up retiring in 2003 from wrestling due to concussion-related issues.

Now Nowinski continues to work as a consultant for Trinity Partners while serving as Co-Founder and President of the Concussion Legacy Foundation (CLF). The organization was founded to solve this concussion crisis in sports and the military through medical research, treatment, and education & prevention. His wrestling career didn't amount to much but the Hockey News listed Nowinski in its 2011 edition of the 100 Most Powerful people in ice hockey. This recognition was attributed to his ability in getting hockey players to donate brain tissue after death

15 15. Scott Steiner (2003)

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Scott Steiner makes the list because he should have been so much more than he was. Choosing to sit and wait until his WCW contract expired, Steiner joined the WWE in 2003 to much fanfare. He was a huge free agent that could have been a big star (like he was in WCW). The problem was, he was terribly out of shape thanks to injuries that made him one of the worst wrestlers in the company but the WWE tried to get around that by using the buzz that came with him returning and making him a babyface.

It made little to no sense the way the company booked Steiner. One of the things that made him so popular in WCW was the fact that he was unhinged and unfiltered, often getting in hot water. It's not that the WWE would have allowed that kind of behavior, but they could have played off of it. There was no reason not to script shoot-style interviews to make Steiner feel very on the edge. That's not what happened at all and he stayed with the company for a few years but was never a main event guy. Today he's known to be one of the craziest former wrestlers on the planet picking beefs with people and saying things that have tarnished his legacy.

14 14. Eugene (2004)

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Eugene was a character meant to stand for something good but wound up being one of the most offensive characters the WWE had ever created. While the company didn't come right out and say Eugene was special needs, it was clear that's what the WWE was insinuating and Eric Bischoff (his on-camera uncle) hated him because of it. He tried to put Eugene in matches that would chase him out of the company but somehow Eugene would overcome.

Amazingly, the character lasted from 2004-2007 but it was bound to phase out, which it did. The character had nowhere to go and the WWE ran out of ideas for him. Nick Dinsmore who played the Eugene character got the raw end of the deal here because it basically cost him any other chance at wrestling for the WWE again. There are not many ways you can go after playing a character with special needs. It would have been offensive (not that it wasn't already) if he'd come back and all of sudden wasn't.

13 13. Tyson Tomko (2005)

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Tyson Tomko actually got four years out of his WWE career, but most fans probably wouldn't remember he was there that long because his entire run was fairly irrelevant. After spending a couple years in development, he made his debut in 2004. He was basically an enforcer for hire and spent most of his time helping Christian.

He got a small push in 2005 in an effort to become a single's wrestler, but it wasn't at all successful. He went on a small winning streak and then lost to John Cena twice in two consecutive weeks. After that, he was pretty much toast. He quit in 2006 and went to wrestle in Japan. I guess he really was an enforcer for hire because he did much better there than in the WWE. He probably made more money too.

12 12. The Highlanders (2006)

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The Highlanders were Robbie and Rory McAllister and they were brought into the WWE at a time that the tag division was at a relatively low point. They could have been an ok team considering the talent they were up against, the but they never made much of their opportunities.

One of the Highlanders (Robbie) pulled an insanely stupid move that pretty much sealed their fate. Just before an opportunity to wrestle at WrestleMania, he went to a taping of Impact Wrestling with TNA and sat in the audience. Of course, TNA put his smiling face on camera and tagged with "WWE Wrestler".  Once the WWE saw this, they released him immediately. To this day, he calls it one of the dumbest career decisions he ever made and he never recovered. It's an unforgiving business and doing something that silly doesn't help your cause.

11 11. Deuce 'n Domino (2007)

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Another tag team that started hot but fizzled quickly, Deuce 'n Domino were tag champs and managed by Cherry Pie. When that didn't last, they then teamed up with Maryse before she was ever connected to The Miz. The group was a throwback to the 50's greaser type gimmick. Cherry Pie wore a poodle skirt and they wore leather jackets with greased hair. It was a gimmick that didn't resonate with the audience at all.

Both wrestlers were released quickly after their debuts. They broke up about a year into the tenures and split brands. Domino actually lasted until about 2009, but one year of being nothing more than enhancement talent was really all they were able to manage. It was a gimmick that probably never stood much of a chance to become much.

10 10. Vladimir Kozlov (2008)

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On the April 4, 2008 episode of SmackDown, Kozlov made his official WWE debut as a villain, with the unique quirk of having no entrance music and no video. He was brought to the ring with a single spotlight that followed him. Much like the Rusev or Braun Stroman characters fans are familiar with today, he won squash matches and demanded better competition.

Kozlov actually had a few opportunities at the WWE Title but he was never a strong wrestler and after he failed to win the belt, the WWE did what they often do with "monsters" who don't win. They made him a comedy sketch. He and Santino Marella were funny for a couple weeks but lost steam quickly. Kozlov is now a successful movie double and stunt man.

9  9. Ezekiel Jackson (2009)

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He was introduced as Brian Kendrick's bodyguard in late 2008 and by the time 2009 rolled around, Jackson was already losing matches after the failed enforcer gimmick had run its course. He was drafted to ECW where he feuded with Vladimir Kozlov and stayed in ECW until the brand disintegrated in early 2010. He actually beat Christian on the final episode and won the ECW Championship. He'll go down in history as the last ever ECW title holder. What a shame for a wrestler who barely lasted over a year to be given that distinction. He wasn't a great wrestler but for that reason alone he made the list. The WWE did a lot of crappy things to the ECW brand, but this was one of the worst.