Calaway made his debut in 1984 for World Class Championship Wrestling (WCCW) under the ring name Texas Red. His first match was a loss against Bruiser Brody. In 1988, after four years in the promotion, he left and joined the Continental Wrestling Association (which became part of the United States Wrestling Association after Jerry Jarrett bought WCCW and merged the two organizations into one), wrestling under several gimmicks.
On February 2, 1989, managed by Dutch Mantel, he debuted as The Master of Pain, a character fresh out of the United States Penitentiary, Atlanta after serving five years (much in solitary confinement) for killing two men in a fight. After his second match the next week, he stayed in the ring by challenging USWA Unified World Heavyweight Champion Jerry Lawler to an impromptu match. The Master of Pain easily dominated Lawler until Mantel entered the ring and called him off. Lawler agreed to a title match, and on April 1, The Master of Pain won his first professional wrestling championship. He held it for just over three weeks before Lawler became the first man to pin him, winning it back. While performing as The Punisher, Calaway won the WCWA Texas Heavyweight Championship on October 5, 1989, when Eric Embry forfeited the title.
In the 1990s, Calaway started his own posse that consisted of fellow Wrestlers Yokozuna, Savio Vega, Charles Wright, The Godwinns, and Rikishi. The faction was called The Bone Street Krew and each member had the initials of the faction tattooed onto themselves, with Undertaker's being prominently shown on his stomach.
In February 1992, The Undertaker's ally Jake "The Snake" Roberts tried to attack "Macho Man" Randy Savage's manager/wife Miss Elizabeth with a steel chair when Undertaker stopped him, becoming a fan favorite for the first time. The turn was solidified on the February 29 episode of Superstars, when Roberts confronted The Undertaker on the Funeral Parlor set over that incident (aired on Saturday Night's Main Event). After demanding to know whose side The Undertaker was on and getting the reply "Not yours!", Roberts attacked both Bearer and The Undertaker, only for Undertaker to stand his ground and run Roberts off. The Undertaker defeated Roberts at WrestleMania VIII. He then feuded extensively with Wrestlers managed by Harvey Wippleman throughout 1992 and 1993, such as Kamala and Giant González. Also in this time, he headlined the first episode of Monday Night Raw on January 11, 1993 with a victory over Damien Demento. He faced González at WrestleMania IX, which is notable as Undertaker's only disqualification win at WrestleMania after the use of chloroform. His rivalry with Yokozuna culminated in a WWF Championship casket match at the Royal Rumble in January 1994. During the match, champion Yokozuna sealed The Undertaker in the casket with the assistance of several other villainous Wippleman-managed Wrestlers to win the match. The Undertaker appeared from inside the casket on the video screen, representing his spirit, warning that he would return. The Undertaker did not appear in the WWF for seven months after his loss to Yokozuna. In reality, he was given time off to allow a back injury to heal.
During his absence, the WWF promoted his return by showing video clips of people who claimed to have seen The Undertaker. After WrestleMania X, Ted DiBiase introduced an Undertaker back to the WWF. This Undertaker, however, played by Calaway's real life cousin, Brian Lee, was an impostor Undertaker (dubbed "The Underfaker" by fans) and led to the return of the real Undertaker in the SummerSlam main event, appearing as a new version of his Deadman persona, represented now by cool colors and replacing grey with purple. The Undertaker defeated the impostor after three Tombstone Piledrivers. At Survivor Series, The Undertaker defeated Yokozuna in a casket match rematch. Throughout most of 1995, Undertaker feuded with members of Ted DiBiase's Million Dollar Corporation. At WrestleMania XI, while The Undertaker was facing King Kong Bundy, Kama stole the urn and antagonized him by melting it into a large gold necklace. In August, Undertaker defeated Kama in a casket match at SummerSlam. Several weeks later, Undertaker injured his orbital bone near his eye, forcing a period of absence for surgery, until his return at Survivor Series.
The Undertaker returned in November at Survivor Series, wearing a Phantom of the Opera-like, grey upper-face mask. In the main event of the Royal Rumble in January 1996, The Undertaker was unmasked in a WWF Championship match against Bret Hart, but Diesel interfered during the match, costing The Undertaker the championship. A rematch for the title on the February 5 episode of Raw saw similar interference. At that month's In Your House: Rage in the Cage, while Diesel was facing Hart in a steel cage match, The Undertaker delivered a surprise attack, emerging from a hole he had ripped through the ring canvas and dragging Diesel with him down under, allowing Hart the victory. After several weeks of more tit for tat between Diesel and The Undertaker, the feud culminated in a singles match between the two at WrestleMania XII, where Undertaker was victorious.
The Undertaker then accepted Michaels' rematch offer, after initially declining, at WrestleMania XXVI in a Streak vs. career match, where Undertaker was victorious and Shawn Michaels was forced to retire. This match also made both the Undertaker and Michaels the first men in WWE history to main event WrestleMania in three different decades. (Undertaker main evented WrestleMania 13 and 24 in 1997 and 2008 and Micheals main evented WrestleMania's 12 and 14 in 1996 and 1998 and the 20th and 23rd editions in 2004 and 2007 respectively.) After a hiatus (which included wrestling two matches on Raw), he returned to SmackDown on May 28, defeating Rey Mysterio to qualify for a spot in the Fatal 4-Way pay-per-view to compete for the World Heavyweight Championship. During the match, The Undertaker suffered a concussion, broken orbital bone, and broken nose; he was visibly bleeding profusely on camera by the end of the match. To cover for the injury, Kane revealed that Undertaker had been found in a vegetative state; Mysterio took his place in the match and won the World Heavyweight Championship. While attempting to learn which Wrestler had attacked The Undertaker, Kane defeated Mysterio to win the World Heavyweight Championship. Kane and Mysterio continued to clash as they accused one another of being the assailant behind the attack.
After building up to his second villainous run in the latter part of 1998, The Undertaker introduced an updated version of his Deadman identity by January 1999 — the dark priest who in the initial period of this persona reigned over a stable known as The Ministry of Darkness. In this form, he took on a wicked, demonic presence, much more so than ever before. He often claimed to be invoking and taking orders from a "Higher Power". Moreover, he often appeared in a hooded black robe and sat on a throne that was specially designed into his character symbol. With the help of his minions, he often performed sacrifices on select WWF Wrestlers, using various incantations and magic words with intent to extract out the dark side of the Wrestlers in question so as to recruit them into his Ministry. The completed Ministry of Darkness consisted of The Brood (Christian, Edge and Gangrel), The Acolytes (Bradshaw and Faarooq), Mideon, and Viscera. Calaway himself did not wrestle for a period having undergone a hip replacement. As part of the angle, Undertaker expressed a Desire to take control of the World Wrestling Federation, displacing its owner, Vince McMahon. These ambitions culminated into a rivalry between The Ministry and The Corporation, ultimately resulting in a match between Undertaker and Corporation enforcer, Big Boss Man. The two faced off in a Hell in a Cell match at WrestleMania XV, which Undertaker won. At Backlash: In Your House, Undertaker defeated Corporation member Ken Shamrock after interference from Ministry member Bradshaw.
To compensate for his lack of physical action, Undertaker became more vocal on the mic, often making smart-aleck remarks and performing commentary. In September 1999, on SmackDown!, Mr. McMahon threatened that he would remove Undertaker from the Unforgiven main event if he refused to participate in a casket match against Triple H. Undertaker retorted that he did not care and maybe he would not be participating in anything, thus walking out of the WWF. In reality, Calaway went on a hiatus from the WWF in order to treat his groin injury. On December 14th he made his return to action, teaming with Viscera in a losing effort against Kane and The Godfather at a house show in Caomo, Puetro Rico.The Undertaker was advertised on the Armageddon promotional poster to return, but meanwhile also tore his pectoral muscle, making him take almost eight months out of action.
Calaway married his first wife, Jodi Lynn, in 1989. They had a son, Gunner Vincent (born 1993). The marriage ended in 1999. Calaway married his second wife, Sara, in St. Petersburg, Florida on July 21, 2000. In 2001, Sara made televised appearances with the WWE (then known as the WWF) as part of a feud between Calaway and Diamond Dallas Page, in which she was acknowledged as being Calaway's wife. The couple had two daughters together: Chasey (born November 21, 2002) and Gracie (born May 15, 2005). In 2007, he and Sara were divorced, and he became romantically linked to former Wrestler Michelle McCool, whom he married on June 26, 2010 in Houston, Texas. The couple's first child, Kaia Faith Calaway, was born on August 29, 2012.
In 2001, the Undertaker reunited with Kane as The Brothers of Destruction, challenging for the WWF World Tag Team Championship once again. They received a title shot at No Way Out, facing Edge and Christian and then champions The Dudley Boyz in a tables match, but they were not successful. The Undertaker then went on to defeat Triple H at WrestleMania X-Seven. He and Kane continued a storyline that focused on Triple H, who formed a "surprise alliance" with then WWF Champion Stone Cold Steve Austin. The Brothers of Destruction were granted an opportunity to face Triple H and Austin for their titles. After The Undertaker and Kane won the WWF World Tag Team Championship from Edge and Christian, Triple H pinned Kane after attacking him with a sledgehammer at Backlash, where The Brothers of Destruction lost their championship. With Kane injured, The Undertaker feuded briefly with Austin for his WWF Championship, but he failed to win the title at Judgment Day.
The Undertaker's next storyline began at the Royal Rumble in January 2002, when Maven eliminated him by hitting him with a dropkick from behind. Subsequently, The Undertaker eliminated Maven in return and brutally assaulted him backstage. On an episode of SmackDown!, The Rock mentioned The Undertaker's elimination at the Royal Rumble, angering Undertaker, who responded by costing The Rock the number one contendership for the Undisputed WWF Championship. The storyline continued when The Rock cost The Undertaker his match with Maven for the Hardcore Championship. The two faced off at No Way Out, where The Undertaker lost due to interference from Ric Flair. This interference began a storyline with Flair, who declined a challenge to wrestle Undertaker at WrestleMania X8, and, as a result, Undertaker assaulted his son David. Flair eventually accepted the match after The Undertaker threatened to inflict the same punishment on Flair's daughter. A no disqualification stipulation was added to the match, and The Undertaker defeated Flair.
The Undertaker took a break after The Big Show threw him off the stage, sparking a feud. The Undertaker returned at the Royal Rumble in January 2003. He immediately continued his feud with Big Show and defeated him by submission at No Way Out with a triangle choke. A-Train entered the storyline by attempting to attack The Undertaker after the match, but Nathan Jones came to his aid. The storyline resumed as The Undertaker began to train Jones to wrestle, and the two were scheduled to fight Big Show and A-Train in a tag team match at WrestleMania XIX. However, Jones was removed prior to the match, making it a handicap match, which The Undertaker won with the help of Jones.
Calaway is a boxing fan and carried the Flag of the United States while leading Team Pacquiao to the ring during the Pacquiao vs. Velázquez fight in 2005. He was also in attendance at the Lennox Lewis vs Mike Tyson fight in 2002.
In January 2006 at the Royal Rumble, The Undertaker returned during Kurt Angle's celebration of his World Heavyweight Championship defense against Mark Henry on a horse-drawn cart, signaling for a title shot. As part of their storyline feud, The Undertaker lost his match with Angle at No Way Out after a thirty-minute match. Undertaker cornered Angle after the match and told him he was not finished with him; however, during a rematch on SmackDown!, Henry attacked The Undertaker from behind, costing him the title. This led to The Undertaker challenging Henry to a casket match at WrestleMania 22, and Henry – like Orton a year before – vowed to end Undertaker's WrestleMania winning streak. The Undertaker defeated Henry to become 14–0 at WrestleMania. During a rematch on the next episode of SmackDown!, The Great Khali made his debut and assaulted The Undertaker to transition into a new storyline.
The Undertaker won his first Royal Rumble match in 2007, in doing so becoming the first man to enter the Rumble at number 30 and win the match. He then began a storyline with Batista, whom he defeated at WrestleMania 23 to win his first World Heavyweight Championship. At Backlash in a Last Man Standing match, they had a rematch that ended in a draw when neither man was able to answer the ten-count, resulting in The Undertaker retaining the championship. On the May 11 episode of SmackDown!, The Undertaker and Batista fought in a steel cage match that ended in a draw when both men's feet touched the floor at the same time. After the match, Mark Henry made his return and assaulted an already exhausted Undertaker, after which Edge ran to the ring and cashed in his Money in the Bank briefcase, forcing Undertaker into a second title defense. Although he kicked out of two quick pin attempts, Undertaker was pinned by Edge after a spear and lost the title.
On the July 25, 2008 episode of SmackDown, Vickie Guerrero reinstated The Undertaker, and scheduled Edge to face him at SummerSlam inside Hell in a Cell, which the Undertaker won. After the match, The Undertaker chokeslammed Edge from the top of a ladder and through the ring canvas. Following this match, Guerrero tried making a peace offering with The Undertaker on SmackDown by apologizing, but The Undertaker told her that he is not the forgiving kind. At Unforgiven, as The Undertaker approached the ring to "take Guerrero's soul" and take her in a casket, Big Show, who appeared at first to aid the Undertaker, betrayed and assaulted him. As a result of this altercation, The Undertaker and Big Show faced each other in a match at No Mercy, where Show won by knockout. At Cyber Sunday, The Undertaker defeated Big Show in a Last Man Standing match after applying the Hell's Gate. At the same time, The Undertaker was engaged in a short feud with Jeff Hardy, who interfered during his match with Vladimir Kozlov. Hardy defeated The Undertaker in an Extreme Rules match the following week on SmackDown due to the interference of Big Show. The Undertaker then went on to defeat Show at Survivor Series in a casket match, to end the feud. At No Way Out, The Undertaker was part of the WWE Championship Elimination Chamber match along with Triple H, Jeff Hardy, Big Show, Vladimir Kozlov and Edge; however, he was unsuccessful at winning the match as he was the runner-up behind Triple H. He then became embroiled in a long time feud with Shawn Michaels over his WrestleMania undefeated streak and the fact that The Undertaker had never defeated Michaels in a singles match previously. The feud culminated in a match at WrestleMania XXV which The Undertaker won. Their match was highly acclaimed by critics and audiences alike and is now considered by many to be one of the greatest WrestleMania matches of all time. On the April 24 episode of SmackDown, after losing a match against Big Show by knockout, Undertaker attacked Show. Following this, Undertaker took another hiatus from the WWE.
Calaway is a mixed martial arts fan, he has been practicing Brazilian jiu-jitsu for a long time, earning a black belt in 2011 under Rolles Gracie, and has attended several Ultimate Fighting Championship (UFC) shows, including a show where Calaway verbally confronted then UFC fighter Brock Lesnar after Lesnar lost to Cain Velasquez. His striking gloves and Hell's Gate submission (a modified gogoplata) were also inspired by mixed martial arts. During a Calaway interview conducted by an internet show after UFC 121, Lesnar walked past him staring. Calaway answered Lesnar's stare by saying "You wanna do it?"
On the January 30, 2012 episode of Raw, The Undertaker returned after a ten-month hiatus to confront Triple H. On the February 13 episode of Raw, Triple H refused The Undertaker's challenge for a WrestleMania rematch. After The Undertaker accused Triple H of living in the Shadow of Shawn Michaels on the February 20 episode of Raw, Triple H accepted the challenge on the condition that it would be a Hell in a Cell match; Michaels was later inserted as special Referee in the match. At WrestleMania XXVIII, The Undertaker, while debuting his new look, a mohawk, defeated Triple H to extend his streak to 20–0. After the match, Undertaker and Michaels carried Triple H to the entrance stage, where the three embraced. Later in 2012, The Undertaker appeared on the 1000th episode of Raw on July 23 to help Kane, who had been confronted by Jinder Mahal, Curt Hawkins, Tyler Reks, Hunico, Camacho, and Drew McIntyre. The Brothers of Destruction overcame and dominated the six other Wrestlers.
The Undertaker was voted the greatest WWE Wrestler ever in a 2013 Digital Spy poll. In naming him the second greatest Wrestler ever, IGN described The Undertaker as, "one of the most respected Wrestlers, and characters, in the business; treated with actual reverence. Like a cherished, invaluable artifact". Luis Paez-Pumar of Complex wrote that The Undertaker character is "easily the best gimmick in the history of professional wrestling". Luke Winkie of Sports Illustrated listed The Undertaker as the fifth greatest Wrestler of all time.
In December 2014, in an out-of-character interview, Vince McMahon confirmed that it was his final decision to have Lesnar end the Streak, and that The Undertaker was initially shocked at the decision. McMahon's reasons for making the decision were that it would significantly enhance Lesnar's formidability to set up the next WrestleMania event and that there were no other viable candidates to fill Lesnar's role.
Calaway has appeared on 61 different pay-per-view posters, which, as of 2015, is the highest of any WWE superstar.
On the February 22, 2016 episode of Raw, Vince McMahon placed his son Shane McMahon, who returned to WWE for the first time since 2009, in a Hell in a Cell match at WrestleMania 32 against The Undertaker with the stipulation that had Shane won, he would have gained control of Raw. Vince later decided that should The Undertaker lose the match against Shane, it would be his final match of WrestleMania. After weeks of mind games and physical confrontations between the pair, Undertaker defeated Shane McMahon at WrestleMania 32 on April 3.
After going undrafted in the 2016 WWE draft, The Undertaker returned for SmackDown Live's 900th episode on November 15, interrupting Edge's Cutting Edge segment, which featured the SmackDown Survivor Series team members as guests, to warn them not to lose against Team Raw at Survivor Series, with Team SmackDown winning the match. The Undertaker made his return on the January 9, 2017 episode of Raw, where he announced his participation in the Royal Rumble match and said he was a free agent. The Undertaker appeared on the January 23 episode of Raw, confronting Brock Lesnar and Goldberg. During the Royal Rumble on January 29, The Undertaker entered at number 29, eliminating Goldberg, The Miz, Baron Corbin and Sami Zayn, before being eliminated by the number 30 entrant, Roman Reigns.
Undertaker took part in Raw 25 Years episode of Raw on January 22, 2018. This was his first post-WrestleMania 33 appearance since his loss to Roman Reigns. On the February 26 episode of Raw, determined to have a match at WrestleMania, John Cena challenged The Undertaker to a match at WrestleMania 34, but said that he was told that the match was impossible. Cena then went on to lose the WWE Championship six-pack challenge at Fastlane. With an unclear path to WrestleMania, Cena decided to put out another challenge to The Undertaker on the March 12 episode of Raw, stating that it was The Undertaker who was keeping the match from happening. Undertaker finally appeared at WrestleMania in April. After Elias confronted Cena and was beaten down, Undertaker's hat and coat appeared in the middle of the ring, where he had left them the previous year, which was then struck by lightning. Afterwards, his hat and coat disappeared, and The Undertaker appeared for an impromptu match. Undertaker beat Cena in what was essentially a squash match, in under three minutes, utilizing his jumping clothesline and Old School maneuvers for the first time since 2015. This was their first singles encounter against each other since the Raw Family Reunion episode of Raw on October 9, 2006 (which ended in a no contest). The Undertaker is scheduled to face Chris Jericho at WWE's Greatest Royal Rumble event in a Casket match.
