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WWE has proven to be the dream workplace for many wrestlers over the years. While some have had to work in different promotions for years to prove their worth before scoring a WWE contract, others have been blessed enough to begin their wrestling career with the company itself. Many Superstars have left the company for different reasons only to return after having varying levels of success in other promotions and in other non-wrestling careers. On the other hand, many Superstars have stuck to the company for decades and will likely continue to re-sign until their retirement, and then stay with the company in some capacity, be it backstage producer, trainer, or ambassador.
In this article, we will look at ten Superstars who were part of WWE in 2000 and earlier, and will be competing for the company for at least a third different decade in 2020.
#10 Shelton Benjamin (2000s, 2010s, 2020s)
Shelton Benjamin may not be a big name in WWE today, but he was definitely a future star when he initially walked into the company in 2000. He signed with WWE and was assigned to Ohio Valley Wrestling (OVW) where he formed the "Minnesota Stretching Crew" with Brock Lesnar.
Benjamin was moved to the main roster in 2002 and was paired up with Charlie Haas to join Kurt Angle. The two came under Angle’s wing and were called 'Team Angle' and saw a lot of success for the next few months before being fired by Angle. They did just fine after that, rechristening themselves ‘The World's Greatest Tag Team’.
Along with Haas, Benjamin was one of WWE’s best tag team wrestlers and won the titles on a few occasions.
After the team broke up during a brand draft, Shelton started a singles run in 2004. He defeated Triple H three times on episodes of RAW and also won the Intercontinental Championship on three separate occasions. He's also a former United States Champion.
Even though Benjamin has been in and out of the company in the last decade, he will be starting the new decade with WWE as a member of the RAW brand.
#9-8 Matt & Jeff Hardy (1990s, 2000s, 2010s, 2020s)
Fans have connected with Matt and Jeff Hardy so well that it’s difficult to digest the fact that the two first appeared for WWE as early as 1994. If you can believe it, they are actually about to enter their fourth different decade as members of the company. At the height of the Attitude Era, the duo was awarded full-time contracts in 1998. Matt and Jeff used a dynamic fast-paced high flying style of wrestling that built them into a lethal force. They became instant crowd favorites.
As The Hardy Boyz, the real-life brothers saw a lot of success and partnered with several Superstars, with Lita proving to be the most popular one, as the trio formed "Team Extreme".
They have no less than eight Tag Team Championship reigns together in the company while scoring even more with other competitors. Individually, they’ve won almost all top titles of the company between the two of them.
While both brothers have gone through several popular gimmicks, and even left and returned to the company on several occasions, it seems like WWE is the right place for them.
Matt Hardy has returned to the ring on RAW in late-2019 after a battle with injury, while Jeff is still out of action due to an injury. However, it feels like we haven’t seen the last of these two men in the ring for WWE yet.
#7 R-Truth (2000s, 2010s, 2020s)
R-Truth may not be as successful as the other men of the list, but he’s had a huge influence and impact on the Superstars taking to the ring today.
Truth sent in a promotional videotape to WWE in 1999, which led to him being signed to a two-year contract under the ring name K-Kwik. In 2000, K-Kwik was promoted to the main roster and put in a tag team with Road Dogg. Soon after, he started competing for the Hardcore division where he was quite successful.
He competed for the company for a couple of years before leaving to join NWA: TNA, where he became the company's second-ever World Champion. After success in that company, he returned in 2008 and picked up from where he’d left off. Truth ran many different gimmicks and clicked with the WWE Universe as a humorous individual who brought them some comic relief. He had several rivalries partnerships with top stars like The Miz, John Cena, and Kofi Kingston, and won the WWE Tag Team Championship with the latter in the process.
Even though Truth may only be seen as an enhancement talent and a humorous part of the roster today, he has done a lot for the company and will most probably walk into 2020 as a 24-time 24/7 Champion.
#6 Big Show (1990s, 2000s, 2010s, 2020s)
Big Show signed a big ten-year contract upon joining WWE in February 1999, where he debuted under his actual name, Paul Wight, to try to help Vince McMahon against rival Stone Cold Steve Austin.
From there onward, Big Show was built as a monster and was regarded as the largest athlete in the world. This allowed him to gain much more attention than any other Superstar, and soon he entered into the WWE Championship picture, winning the belt in November 1999 at Survivor Series.
Big Show is a 5-time World Champion, and he has also thrived as a tag team competitor. He’s won the Tag Team Championships eight times in his career with men such as Kane, The Miz, Chris Jericho, and The Undertaker.
Not only has Big Show been a constant for WWE for over two decades, but he has also been extremely loyal to them too and remained with them for most of his career.
With injuries taking a toll on him, The Giant is on the sidelines at the moment, but it seems apparent that we may see him make a return in 2020 to have one final run before hanging up his boots.
#5 Brock Lesnar (2000s, 2010s, 2020s)
Brock Lesnar, just like Shelton Benjamin, walked into the company in 2000 under a developmental contract. He was assigned to Ohio Valley Wrestling where he first met Paul Heyman. Along with former college roommate Benjamin, Lesnar started his career as a tag team wrestler and was seen as a breakout star.
He later joined forces with Heyman, who managed him from his debut on the night after WrestleMania x-8 in 2002 until Heyman left him and joined Big Show in November of that year. Heyman's original hype man style helped him reach the heights where he is today, especially with the duo back together since Brock's WWE return in 2012.
Lesnar became the WWE Champion within his first 5 months on the main roster, and held the championship on 4 different occasions before his untimely departure from the company only 2 years after his debut on RAW. Even though the Superstar left the company to try his hands at different sports, he ended up returning to his roots and benefiting more than any other Superstar.
One of Lesnar’s biggest achievements came in 2014 when he broke The Undertaker’s 21-match WrestleMania undefeated streak at WrestleMania XXX.
The Mayor of Suplex City has never won a mid-card title in his entire career, nor has he ever scored a Tag Team Championship while on the main roster. However, he is a 3-time Universal Champion and a 5-time WWE Champion. Lesnar will be walking into the new decade as a member of the RAW brand and the current WWE Champion.
#4 Kane (1990s, 2000s, 2010s, 2020s)
The Big Red Machine competed in his first dark match as early as in 1995 on RAW. Many fans would remember him appearing on RAW as Jerry Lawler’s private dentist in 1995.
He first appeared as Kane in 1997 when he helped Shawn Michaels defeat The Undertaker in the first Hell in a Cell match. The company heavily built him up before the debut, but never showed what he looked like until that night in October. He was soon revealed to be The Undertaker’s half-brother and the storyline helped both men build up their characters excessively with the aid of Paul Bearer.
Undertaker and Kane later formed The Brothers of Destruction, a team that was feared by every single individual in the locker room. The two men built up in the 2000s, and Kane led some good singles storylines, including his unmasking in 2002 at the hands of Triple H.
Kane has stayed with the company since his debut and won a number of Championships during his time. He’s managed to bag each title at least once in his career, except for the United States Championship. Not only has he built his character as one of the most talked-about gimmicks in the company’s history, but he also helped other new stars grow around him.
Kane has taken a hiatus from wrestling as he has gotten into politics recently, but we expect him to make a few sporadic appearances for the company heading into 2020.
#3 Triple H (1990s, 2000s, 2010s, 2020s)
Triple H signed a contract with World Championship Wrestling (WCW) in 1994. He was let go from that contract and quickly signed with WWE in 1995. He became known as the Connecticut Blue Blood Hunter Hearst Helmsley and made his in-ring debut at SummerSlam that year, where he defeated Bob Holly.
That marked the beginning of a remarkable career that has spanned almost two and a half decades. Almost every gimmick Triple H touched turned to gold in WWE, and his factions D-Generation X and Evolution are known as two of the best factions in the company’s history.
Over the span of 25 years, Triple H has won 14 World Championships, and several other championships to become one of the most decorated stars in the industry.
In recent years, Triple H has been working as an executive in the company and after the passing of Dusty Rhodes, began to dedicate a significant amount of time to NXT, which has developed into another great wrestling brand for the company.
Since putting on the suit, Triple H has featured in far fewer matches than he used to during his early days. His most recent match was at this past year's WrestleMania 35, defeating Batista in the latter's retirement match. The Game has always returned to the ring to reignite some great angles, and we’re sure he won’t hang up his boots without having a retirement match of his own.
#2 John Cena (2000s, 2010s, 2020s)
John Cena made his unofficial debut for WWE in 2000 in a dark match before a taping of SmackDown. He continued to compete in dark matches before signing a contract with the company in 2001, after which he was assigned to Ohio Valley Wrestling.
Cena made his television debut in June 2002 when he answered an open challenge from Kurt Angle. He fought well in the match and came close to victory before getting pinned by Angle.
After that performance Cena became a quick fan-favorite, and there was no stopping him from there. He led some of the most famous and memorable gimmicks in the company’s history and became one of the biggest merchandise movers for the company as well.
This has allowed Cena to become one of the most decorated Superstars in the industry, as he is a 16-time World Champion and has also held the United States and Tag Team Championships.
Cena has become one of the biggest names in the entertainment industry, as he has recently been successful out of the ring starring in movies and television shows.
Even though The Doctor of Thuganomics only works a few matches a year now owing to his tough filming schedule, there is almost no doubt that we will see him compete in a couple of matches in the coming year.
#1 The Undertaker (1990s, 2000s, 2010s, 2020s)
A name that’s synonymous with WWE, The Undertaker joined the company in November 1990 as Kane the Undertaker. His gimmick saw him portray a character who was impervious to pain.
As time went by, The Undertaker became one of the most followed and loved wrestlers in WWE. Undertaker’s character and gimmick allowed WWE to come up with unique matches such as Buried Alive matches and Casket matches. Over time, he became known as The Deadman, The Phenom, the motorcycle-riding American Bad A**, and Big Evil.
Each and every gimmick worked with the Superstar, as he was a crowd favorite no matter what character he was playing. Throughout his WWE career, he won 7 World Championships and held the Tag Team Championship on multiple occasions.
However, The Phenom was much bigger than the championships he held, and the company realized that and built him as a completely different Superstar. Defeating The Undertaker was an achievement by itself, and his WrestleMania undefeated streak (he eventually lost and sits at 22-2) remains one of the most iconic achievements in wrestling history.
The Undertaker only works a few matches a year now, and usually appears for big events such as Crown Jewel and WrestleMania. He has missed only 2 WrestleMania events since his first in 1991 - WrestleMania 2000 due to an injury, and this year's WrestleMania 35, as he has taken a much lighter schedule and was not asked to be a part of the event.
2020 will mark his 30th year in the company, and we’re sure that he will take to the ring once again to celebrate the milestone, and maybe even compete in his final WrestleMania match.
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