The Undertaker

Birth name: Mark William Calaway
Born/Date of Birth: March 24, 1965 (age 55)
Place of Birth: Houston, Texas, United States
Residence: Austin, Texas, United States
Spouse(s): Jodi Lynn(m. 1989; div. 1999), Sara Frank(m. 2000; div. 2007), Michelle McCool(m. 2010)
Children: 4
Professional wrestling career
Ring name(s): Cain the Undertaker
Mark Callous
Mean Mark Callous
Mean Mark
Dice Morgan
The Master of Pain
The Punisher
Texas Red
The Undertaker
Billed height: 6 ft 10 in (208 cm)
Billed weight: 309 lb (140 kg)
Billed from: Death Valley
Houston, Texas
Trained by: Buzz Sawyer
Debut: June 26, 1987
Retired: 2020
Mark William Calaway (born March 24, 1965), better known by the ring name The Undertaker, is a former American professional wrestler who was signed to WWE. He announced his retirment from professional wrestling on June 21, 2020 via final episode of his documentary series, The Last Ride.

Calaway began his career in 1987, working as various gimmicks for World Class Championship Wrestling (WCCW) and other affiliate promotions, and he became USWA Unified World Heavyweight Champion and WCWA Texas Heavyweight Champion during this time. After signing with World Championship Wrestling (WCW) in 1989, he had a brief stint in the mid-card as "Mean Mark" Callous, before joining the World Wrestling Federation (WWF, now WWE) in 1990.

Calaway was rebranded as "The Undertaker" in the WWF, and gained significant mainstream popularity as a horror-themed, macabre entity who employed scare tactics and held links to the supernatural. The longest-tenured wrestler in company history at 30 years, The Undertaker was one of the most prominent figures of the Attitude Era, a boom period in the company's business in the latter 1990s. His character transitioned into a biker in the early 2000s, before returning to a refined version of his previous gimmick in 2004. The Undertaker is heavily associated with WWE's flagship annual event, WrestleMania, where he became known for The Streak, a series of 21 straight victories, and he headlined the event on five occasions.[a]

He is also known for his pairing with storyline half-brother Kane, with whom he has alternatively feuded or teamed as The Brothers of Destruction since 1997. With Kane, he held the WWF and WCW World Tag Team Championships during The Invasion storyline. Widely regarded as one of the greatest professional wrestlers of all time, The Undertaker is a seven-time world heavyweight champion in WWF/E, having held the WWF/E Championship four times and World Heavyweight Championship three times.

Early life
Calaway was born in Houston, Texas, on March 24, 1965, the son of Frank Compton Calaway (died July 22, 2003) and Betty Catherine Truby. He has four older brothers: David, Michael, Paul and Timothy (died 2020). He attended Waltrip High School, where he was a member of the football and basketball teams. He graduated in 1983 and began studying at Angelina College in Lufkin, Texas on a basketball scholarship. In 1985, he enrolled in Texas Wesleyan University in Fort Worth, Texas, where he majored in sport management and played basketball for the Rams in the 1985–1986 season as a center. In 1986, Calaway dropped out of university to focus on a career in sports and briefly considered playing professional basketball in Europe, before deciding to focus on professional wrestling.

Professional wrestling career
Early career (1987–1990)
Calaway began training under Buzz Sawyer in late 1986; he disliked Sawyer, who reportedly lacked commitment and provided a limited education. Performing under a mask as Texas Red, Calaway wrestled his first match on June 26, 1987 for World Class Championship Wrestling (WCCW), losing to Bruiser Brody at the Dallas Sportatorium. He was accompanied to the ring by Percival "Percy" Pringle III, who would later serve as his manager in the WWF (as Paul Bearer). Two myths have circulated regarding Calaway's beginnings in the industry, the first being that he made his in-ring debut in 1984, and the second being that he was trained by former WCCW colleague Don Jardine (aka The Spoiler). While never trained by Jardine, Calaway was an admirer of his work and would inherit his signature top rope walk.

In 1988, Calaway joined the Continental Wrestling Association (which became part of the United States Wrestling Association (USWA) 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 was reintroduced 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.

World Championship Wrestling (1989–1990)
In 1989, Calaway joined World Championship Wrestling (WCW) as a villain and adopted the ring name "Mean Mark" Callous, a name devised for him by Terry Funk. He was portrayed as a morbid character; he wore predominantly black ring attire and was described by announcer Jim Ross as having a fondness for pet snakes and the music of Ozzy Osbourne. Callous was promptly drafted into The Skyscrapers tag team to replace a legitimately injured Sid Vicious and he made his debut on January 3, 1990, in a match later televised against Agent Steel and Randy Harris. The new team gained some notoriety at Clash of the Champions X when they beat down The Road Warriors after their match. However, Callous' partner Dan Spivey left WCW days before their Chicago Street Fight against The Road Warriors at WrestleWar. Callous and a replacement masked Skyscraper were defeated in the street fight and the team broke up soon afterwards. Now a singles wrestler, Callous took on the guidance of Paul E. Dangerously (Paul Heyman) and defeated Johnny Ace at Capital Combat and Brian Pillman at Clash of the Champions XI: Coastal Crush.

Calaway began to question his future in WCW after being told by booker Ole Anderson, during contract renewal talks, that nobody would ever pay money to watch him perform. Callous wrestled Lex Luger for the NWA United States Heavyweight Championship at The Great American Bash, but was pinned. According to WWF/E executive Bruce Prichard, "feelers" had already been sent out to the WWF by Heyman: Calaway wrestled the match with a dislocated hip knowing that he was being watched by Vince McMahon. McMahon initially did not express interest, but Prichard encouraged him to speak with Calaway when WCW traveled to New Jersey for a house show in the Meadowlands on August 24. The meeting between the two went well and Calaway gave notice to WCW on August 27. His final match was on September 7 at a WorldWide taping in Amarillo, Texas in which he defeated Dave Johnson.

During his time in WCW, Calaway briefly wrestled in New Japan Pro Wrestling (NJPW) as "Punisher" Dice Morgan. After leaving WCW, he briefly returned to the USWA to participate in a tournament to determine the new USWA Unified World Heavyweight Champion; he defeated Bill Dundee in the first round, but lost to Jerry Lawler in the quarterfinals.

World Wrestling Federation/Entertainment/WWE
Debut and early feuds (1990–1991)
In October 1990, Calaway signed with the World Wrestling Federation (WWF). He made his debut as Kane the Undertaker at a taping of Superstars on November 19, 1990. Calaway made his official on-camera debut on November 22 at Survivor Series as a villainous character when he was the mystery partner of Ted DiBiase's Million Dollar Team. Approximately one minute into the match, The Undertaker eliminated Koko B. Ware with his finisher, the Tombstone Piledriver. He also eliminated Dusty Rhodes before being counted out; however, his team won the match with DiBiase being the sole survivor. During the match, Calaway was referred to as The Undertaker, omitting the name 'Kane', which was dropped shortly after the event (and seven years later was given to another wrestler who eventually became Undertaker's younger brother of the same name). At the same time, The Undertaker switched managers from Brother Love to Paul Bearer – a histrionic, ghostly character, almost always seen bearing an urn, which he used to revive The Undertaker's strength whenever Undertaker fell victim to his opponents. Undertaker placed his defeated opponents (almost always jobbers) in a body bag and carried them to the back. Throughout the end of 1990, The Undertaker mostly picked up squash victories against jobbers on Superstars of Wrestling and Wrestling Challenge tapings. He was a participant in the 1991 Royal Rumble match which was won by Hulk Hogan. He continued picking up victories in squash matches leading up to his first feud in the WWF with "Superfly" Jimmy Snuka.

WWF Champion (1991–1994)
He made his WrestleMania debut at WrestleMania VII on March 24, 1991, quickly defeating "Superfly" Jimmy Snuka. He began his first major feud with The Ultimate Warrior when he attacked Warrior and locked him in an airtight casket on the set of Paul Bearer's Funeral Parlor interview segment. He would later lose to Warrior in the first-ever body bag challenge in WWF history. At King of the Ring 1991, Undertaker defeated Animal in a qualifying match before fighting Sid Vicious to a double disqualification in the Semi-Final, which saw both men eliminated from the King of the Ring tournament. The Undertaker defeated Hulk Hogan to win his first WWF Championship at Survivor Series with the help of Ric Flair and thus became the youngest WWF Champion in history, until having this record broken by Yokozuna in April 1993 at WrestleMania IX. WWF President Jack Tunney ordered a rematch for This Tuesday in Texas six days later, where he lost the title back to Hogan. However, due to the controversial endings of the two title matches between The Undertaker and Hogan, the title was vacated by Tunney. The title was awarded to Ric Flair as the winner of the 1992 Royal Rumble match.

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 XXX). 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. According to Callaway, working with González was "It was survival every night trying to figure out what he could do" and "took years off my career". 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.

The original Deadman Era (1994–1996)
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 gray 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, gray upper-face mask. 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's next feud started the next night on Raw, when Mankind made his debut and interfered in Undertaker's match against Justin "Hawk" Bradshaw. For the next few months, Mankind ambushed and cost The Undertaker several matches. The feud intensified and they began taking their battles into crowds, backstage areas and in the boiler rooms of different arenas. Mankind cost The Undertaker the WWF Intercontinental Heavyweight Championship at In Your House 8: Beware of Dog, assisting champion Goldust to victory. As a result, the first-ever Boiler Room Brawl was booked between the two at SummerSlam. During the match, when Undertaker reached for Paul Bearer's urn, Bearer hit him with it, betraying The Undertaker and allowing Mankind to "incapacitate" him with the mandible claw, giving him the win. After Bearer's betrayal, The Undertaker took his rivalry with Mankind to a new level, resulting in a Buried Alive match in the main event of In Your House 11: Buried Alive, where The Undertaker won the match after a chokeslam into the open grave. However, after interference from The Executioner, as well as the help of several other wrestlers, The Undertaker was ultimately "buried alive".

Lord of Darkness (1996–1998)
After being buried alive, The Undertaker returned at Survivor Series again pitting him against Mankind, but with a unique stipulation; hanging 6.1 m (20 ft) above the ring was Paul Bearer, enclosed in a steel cage. If Undertaker won the match, he would be able to get his hands on Bearer. Even though The Undertaker won the match, interference from The Executioner enabled Bearer to escape Undertaker's clutches. Following Survivor Series, The Undertaker briefly turned his attention to The Executioner, who had been interfering in his matches since his arrival. At In Your House 12: It's Time, The Undertaker defeated The Executioner in an Armageddon rules match. He then moved on to feud with Vader, whom he faced in January 1997 at the Royal Rumble in a singles match, which Undertaker lost after Bearer interfered on behalf of his new protégé. The two then clashed in the Royal Rumble match itself as they made it to the final moments of the match, but both were eliminated by Stone Cold Steve Austin, who had crept back into the match after his elimination was unseen. He faced both Vader and Austin in a four-corners elimination match for the vacant WWF Championship at In Your House 13: Final Four, but Bret Hart won. However, the following month, The Undertaker managed to win the title for the second time by defeating Sycho Sid at WrestleMania 13.

In May 1997, Paul Bearer attempted to rejoin The Undertaker, using the ultimatum of revealing The Undertaker's "deepest, darkest secret" to the world. Bearer accused The Undertaker of having burned down the family funeral home business when he was a child, killing his parents and ostensibly his younger half-brother as well. The Undertaker denied all this; however, Bearer claimed to have proof in the form of The Undertaker's alive and well half-brother Kane, who had survived though scarred and burned. Bearer raised Kane after the fire, having him institutionalized from the date of the fire into adulthood. Ever since the fire, Kane had been awaiting to exact vengeance on his older half-brother. In defense, Undertaker responded that Kane, a pyromaniac, had been the one to set the fire and could not have possibly even survived. Also during the period, Bearer had unintentionally admitted to Undertaker's mother having an affair with him. As a result, it was revealed to The Undertaker that Kane was his half-brother. Until that point, Undertaker spent his life (the entirety of the father's life) under the impression that Kane was fully related to him and his family. It was during this time that The Undertaker also made an appearance in Michinoku Pro Wrestling, defeating Hakushi in a singles match.

Concurrent to the deep, dark secret storyline directed by Bearer, Undertaker began a new rivalry at SummerSlam when special guest referee Shawn Michaels accidentally hit The Undertaker with a steel chair shot meant for Bret Hart, costing Undertaker the WWF Championship. After a double count-out draw during Ground Zero: In Your House, Undertaker challenged Michaels to the first Hell in a Cell match at Badd Blood: In Your House. During this match, The Undertaker's storyline half-brother Kane finally made his debut under the control of Paul Bearer, ripping off the door to the cell and giving The Undertaker a Tombstone Piledriver, Undertaker's trademark finisher, allowing Michaels to pin him. As the storyline progressed through Bearer, Kane challenged The Undertaker, but Undertaker consistently refused to fight his half-brother. The Undertaker's final encounter with Michaels was in a casket match at the Royal Rumble. The week before on Raw, Kane had seemed to ally with his brother against Michaels' D-Generation X; however, at the event, Kane trapped him in the coffin, padlocking the casket lid and setting it ablaze which again gave Michaels the victory. The Undertaker, however, had disappeared when the casket lid was reopened. After a two-month hiatus, The Undertaker returned and defeated Kane at WrestleMania XIV. The two had a rematch, the first-ever Inferno match, one month later at Unforgiven: In Your House, which The Undertaker won by setting Kane's right arm on fire.

The Undertaker's feud with Mankind was concluded afterward and they faced each other in a Hell in a Cell match at King of the Ring. During the match, The Undertaker threw Mankind off the roof of the 4.9 m (16 ft) cell onto a broadcast table below, in what was a preplanned move. He later performed a chokeslam on Mankind through the roof of the cell into the ring which legitimately knocked Mankind unconscious. Mankind also used thumbtacks in the match and was hit by a back body drop and another chokeslam onto them before Undertaker won the match with the Tombstone Piledriver. The Undertaker then became the number one contender for the renamed WWF Championship at SummerSlam, now held by Austin. Shortly before SummerSlam, however, The Undertaker revealed that he and Kane were working together as brothers. Despite this revelation, The Undertaker told Kane that he did not want him to interfere in the match with Austin and even though The Undertaker lost the match, he handed Austin his championship belt back after the match in a show of respect. In September, the storyline continued and The Undertaker began to show some villainous characteristics when he and Kane revealed the fact that they were in cahoots to rid Austin of his title for Mr. McMahon. At Breakdown: In Your House, The Undertaker and Kane were booked in a triple threat match with Austin for the WWF Championship, in which McMahon stated that the brothers were not allowed to pin each other. The Undertaker and Kane pinned Austin simultaneously after a double chokeslam, so the title was vacated by McMahon. This event led to a match at Judgment Day: In Your House between The Undertaker and Kane for the title, with Austin as the special guest referee. Near the end of the match, Paul Bearer seemed about to assist Kane by handing him a steel chair to hit The Undertaker with, but as Kane had his back turned, both Bearer and The Undertaker hit Kane with the chair. The Undertaker went for the pin, but Austin refused to count the fall, attacked The Undertaker and counted out both of them. Finally, The Undertaker became a villain the next night on Raw for the first time in over six years, reconciling with Bearer and claiming that he and Bearer would unleash their "Ministry of Darkness" on the World Wrestling Federation. As part of this new storyline, he admitted that he had indeed set the fire that killed his parents, for which he had previously blamed Kane.

Ministry of Darkness (1998–1999)
After Survivor Series, The Undertaker returned his attention to his previous feud with Austin for costing him the title at Judgment Day, hitting Austin in the head with a shovel during a title match with The Rock, returning the favor for what happened a month earlier. With this twist in the storyline, Mr. McMahon scheduled a Buried Alive match between The Undertaker and Austin at Rock Bottom: In Your House. In the weeks leading up to Rock Bottom, The Undertaker attempted to embalm Austin alive, tried to have Kane committed to a mental asylum and had his druids chain Austin to his symbol, raising it high into the arena. However, The Undertaker lost the match after Kane interfered.

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 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, Mr. 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.

Thereafter, The Undertaker kidnapped Stephanie McMahon, forcing Mr. McMahon to enter into a reluctant alliance with his longtime nemesis Stone Cold Steve Austin. The Undertaker attempted to marry Stephanie before sacrificing her in an eldritch ceremony conducted by Paul Bearer, but Austin was able to rescue her.

The Undertaker then began a storyline where he teamed with Big Show in a tag team known as "The Unholy Alliance", which held the WWF World Tag Team Championship twice. After their victory at SummerSlam, The Undertaker suffered a groin tear and was seen limping in several matches. He avoided competing in wrestling matches in the following weeks, instead tyrannically ordering Big Show to fight all his battles and oblige all his many wishes. He also began to transition away to the biker character he would play in 2000. Per an interview with Kevin Nash, this was a move to allow Calaway to enter World Championship Wrestling with a non-trademarked persona. Had he entered WCW, it would have been as Mark Calaway. Although negotiations were described as close, he ultimately re-signed with the World Wrestling Federation.

To compensate for his lack of physical activity, 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. He made his return to action on December 14, teaming with Viscera in a losing effort against Kane and The Godfather at a house show in Coamo, Puerto 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.

American Bad Ass (2000–2001)
In May 2000, The Undertaker made his return under a new character, the American Bad Ass. When Undertaker returned near the end of the Iron Man match between Triple H and The Rock at Judgment Day, he took out all the members of the McMahon-Helmsley Faction, which caused him to once again be a fan favorite. This incident led to another match between the two at SummerSlam, which ended in a no contest as Kane ran from the ring area after The Undertaker removed Kane's mask.

The Undertaker then challenged Kurt Angle for the WWF Championship at Survivor Series. Angle, however, defeated The Undertaker after he switched places with his real-life brother, Eric Angle. The Undertaker demanded and was awarded a spot in the six-man Hell in a Cell match for the WWF Championship at Armageddon. The Undertaker promised to make someone famous and did so when he performed a chokeslam on Rikishi from the roof of the cell.

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 championships. With Kane injured, The Undertaker feuded briefly with Austin for his WWF Championship, but he failed to win the title at Judgment Day.

As part of "The Invasion" storyline, The Undertaker's next nemesis was Diamond Dallas Page, who was obsessively following The Undertaker's wife, Sara. At SummerSlam, WCW Tag Team Champions The Undertaker and Kane defeated Page and his partner Chris Kanyon in a steel cage match to win the WWF World Tag Team Championship. At Survivor Series, The Undertaker teamed with Kane, The Rock, Chris Jericho and Big Show to take on The Alliance's Stone Cold Steve Austin, Booker T, Rob Van Dam, Shane McMahon and Kurt Angle (this was the last time The Undertaker and Kane teamed until 2006). Angle pinned The Undertaker due to interference by Austin.

Big Evil (2001–2003)
After The Alliance was defeated, The Undertaker became a villain once again by forcing commentator Jim Ross to kiss Vince McMahon's buttocks. This was the beginning of a new persona for The Undertaker, as he cut his long hair short and called himself "Big Evil". At Vengeance, The Undertaker defeated Rob Van Dam to win the WWF Hardcore Championship.

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. As a result, Undertaker assaulted his son David Flair. 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.

After the storyline with Flair, The Undertaker was drafted to the Raw brand after WWF split its roster into two brands and defeated Stone Cold Steve Austin at Backlash to become the number one contender to the Undisputed WWF Championship. Later that night, he helped Hollywood Hulk Hogan win the title against then-champion Triple H. The Undertaker then defeated Hogan for the renamed WWE Undisputed Championship at Judgment Day. The next night on Raw, The Undertaker lost to Rob Van Dam for the WWE Undisputed Championship; however, Ric Flair restarted the match and The Undertaker regained the championship. On the July 1 episode of Raw, The Undertaker became a fan favorite again after defeating Jeff Hardy in a ladder match and raising Hardy's hand as a show of respect. The Undertaker, however, lost the title at Vengeance to The Rock in a triple threat match that also involved Kurt Angle. On the August 29 episode of SmackDown!, Undertaker was moved to the SmackDown! brand (where he remained until the first brand extension ended in 2011), alongside former Raw talent Brock Lesnar, Chris Benoit and Eddie Guerrero. Undertaker defeated Chris Benoit and Kurt Angle in a triple threat match to become the #1 contender for the renamed WWE Championship and challenged Brock Lesnar for the title at Unforgiven that ended in a double disqualification. Their feud carried over to No Mercy in a Hell in a Cell match, which The Undertaker performed in the match with a legitimately broken hand and eventually lost to the champion.

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 before the match, making it a handicap match, which The Undertaker won with the help of Jones.

Over the remainder of the year, The Undertaker entered a brief feud with John Cena and was booked to have two WWE Championship opportunities. The first, on the September 4 SmackDown!, against Kurt Angle, ended in a no contest, due to interference from Brock Lesnar.

Return of The Deadman (2004–2007)
In the storyline leading up to WrestleMania XX, Kane was haunted by vignettes proclaiming The Undertaker's return. The first was during the Royal Rumble when The Undertaker's bells tolled, distracting Kane and allowing Booker T to eliminate him. At The Great American Bash, Undertaker fought a handicap match against The Dudley Boyz, with the stipulation that if he did not lay down and purposely lose, Heyman would bury Paul Bearer in cement. The Undertaker won and stopped Heyman from burying Bearer, but after claiming Bearer was merely a liability he had no use for, buried him himself.

The Undertaker began a feud with then WWE Champion John Bradshaw Layfield (JBL) by challenging him to a title match at SummerSlam, which The Undertaker lost by disqualification. At No Mercy, The Undertaker and JBL competed in the first-ever Last Ride match, although The Undertaker lost after Heidenreich interfered. After defeating Heidenreich in a match at Survivor Series, The Undertaker turned his focus to the WWE Championship once again. Along with Eddie Guerrero and Booker T, he challenged JBL to a championship rematch at Armageddon in a fatal four-way match, in which The Undertaker was unsuccessful, again due to Heidenreich's interference. The feud culminated in a casket match between The Undertaker and Heidenreich at the Royal Rumble, where Undertaker sealed Heidenreich in a casket for the victory.

Soon after, Randy Orton challenged The Undertaker to a match at WrestleMania 21 and claimed that he would end his WrestleMania winning Streak.

In one of the most controversial moments in the WWE, on the episode of SmackDown! taped on July 4, 2005, the SmackDown! General Manager Theodore "Teddy" Long put Muhammad Hassan in a match against Undertaker at The Great American Bash and placed Daivari in a match that night against The Undertaker, who quickly defeated Daivari. After the match, Hassan began to "pray" on the ramp, summoning five masked men, dressed in black shirts, ski-masks and camouflage pants. Armed with clubs and a piano wire, the masked men beat and choked The Undertaker and Hassan put The Undertaker in a camel clutch. Afterward, the masked men lifted Daivari above their heads and carried him away. Three days later, the London bombings took place. The footage aired unedited on UPN in the United States and on The Score in Canada with an advisory warning shown several times during the broadcast. It was removed from the Australian and European (including in the United Kingdom) broadcasts.

The angle elicited national attention in the New York Post, TV Guide, Variety and other major media outlets. In response to the criticism, UPN decided that it would monitor the storyline closely and that it did not want the Hassan character on its network that week. Hassan later delivered a promo to the live crowd for the July 14, 2005, episode of SmackDown!, but when UPN announced that the segment would be edited, WWE decided to host the video of the segment on its official website. In the segment, Hassan reiterated that he was an Arab-American and that the American people automatically and unfairly assumed that he was a terrorist. Despite being in character, he referred to the real-world media coverage of the storyline, singling out the New York Post's Don Kaplan by name and denouncing his description of the events on SmackDown!, such as Kaplan's comment of the masked men being "Arabs in ski masks". On the July 14, 2005, episode of SmackDown!, Hassan's absence was explained by a statement delivered by his attorney Thomas Whitney, Esquire which said that Hassan refused to appear on the show until The Great American Bash due to the way he had been treated by the media and WWE fans.

It was revealed in late July 2005 that UPN had pressured WWE to keep Hassan off their network, effectively removing him from SmackDown!. Undertaker defeated Hassan at The Great American Bash to become the number one contender to the World Heavyweight Championship. After the match, The Undertaker delivered a Last Ride through an open stage ramp onto a concrete floor to Hassan. It was reported that Hassan sustained serious injuries and had to be rushed to a nearby medical facility, writing Hassan off television. Several days later, WWE.com hosted a video of a kayfabe announcement from Theodore Long, where he reiterated the stipulation that Hassan would no longer appear on SmackDown!. It was revealed years later that Hassan was about to receive a major push by winning the World Heavyweight Championship from Batista at SummerSlam and thus breaking Randy Orton's record for being the youngest World Heavyweight Champion in WWE history.

On the following episode of SmackDown!, The Undertaker lost to JBL in a number-one contender's match, once again due to interference from Orton. After winning the match, Calaway took a brief hiatus from professional wrestling.

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, signalling for a title shot. As part of their storyline feud, The Undertaker lost his match with Angle at No Way Out after a 30-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 was not heard from until the May 5 episode of SmackDown!, as Theodore Long delivered a challenge from The Undertaker to Khali for a match at Judgment Day.

The Undertaker's next match was with then United States Champion Mr. Kennedy at No Mercy, but was disqualified in the match after he hit Kennedy with the championship belt. As part of the storyline, Kennedy defeated The Undertaker in a First Blood match at Survivor Series after interference from MVP, but finally defeated Kennedy in a Last Ride match at Armageddon. The two continued to feud into 2007 as Kennedy cost The Undertaker two World Heavyweight Championship opportunities for a championship match at the Royal Rumble. However, The Undertaker eventually qualified for the 2007 Royal Rumble match, by winning a battle royal on the January 26 episode of SmackDown!.

World Heavyweight Champion (2007–2010)
The Undertaker won his first Royal Rumble match, on January 28, 2007, in doing so becoming the first man to enter the Rumble at number 30 and win the match, after lastly eliminating Shawn Michaels. On the February 5 episode of Raw, Undertaker elected to face World Heavyweight Champion Batista at WrestleMania 23, before attacking him with the chokeslam. At No Way Out, Undertaker and Batista reluctantly teamed together to challenge John Cena and Shawn Michaels for the World Tag Team Championship, but failed to win after Batista gained revenge on Undertaker by hitting him with a spinebuster, allowing Cena to pin him. At WrestleMania 23 on April 1, Undertaker defeated Batista to win his first World Heavyweight Championship and extend his Streak to 15–0. Undertaker faced Batista in a rematch at Backlash, this time in a Last Man Standing match. The match ended in a draw after neither man got to their feet by the referee's count of ten, meaning The Undertaker retained the championship. The Undertaker and Batista then fought once again in a steel cage match on the May 11 episode of SmackDown! that also 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 two spears and lost the title. After this match, Undertaker took time off due to a torn right biceps.

During his rehabilitation, Henry bragged about his assault on Undertaker, until vignettes began playing promoting The Undertaker's return. The Undertaker returned at Unforgiven on September 16, defeating Henry. Batista and The Undertaker reignited their feud at Cyber Sunday with the fans choosing the special guest referee Stone Cold Steve Austin, but Batista retained the title. They battled again inside Hell in a Cell at Survivor Series, where Edge returned and interfered to help Batista retain the World Heavyweight Championship. In response to this, The Undertaker delivered a Tombstone Piledriver to General Manager Vickie Guerrero on the next SmackDown!, sending her to the hospital. Returning assistant-General Manager Theodore Long declared a triple threat match for the title between the three men at Armageddon, which Edge won after interference from The Major Brothers (Curt Hawkins and Zack Ryder).

At the Royal Rumble, Undertaker competed in the Royal Rumble match on January 27, 2008, entering at number 1, but was eliminated by Shawn Michaels. At No Way Out, The Undertaker defeated Batista, Finlay, The Great Khali, MVP and Big Daddy V in an Elimination Chamber match to become the number one contender for Edge's World Heavyweight Championship at WrestleMania XXIV, where he defeated Edge with the Hell's Gate submission hold, to win his second World Heavyweight Championship in his 16th WrestleMania win. In a WrestleMania rematch, The Undertaker defeated Edge once again at Backlash to retain the World Heavyweight Championship. Vickie Guerrero then banned The Undertaker's Hell's Gate submission hold and stripped him of the title on the May 2 episode of SmackDown. The Undertaker battled Edge for the vacant title at Judgment Day, which he won by countout. Guerrero ordered that the title remain vacant, because titles could not change hands in this way. Edge and The Undertaker faced each other again for the vacant championship at One Night Stand in a Tables, Ladders, and Chairs match, which The Undertaker lost after interference from La Familia. As a result of the stipulation, Undertaker was forced to leave WWE.

On the July 25 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 Big Show won by knockout. At Cyber Sunday, The Undertaker defeated Big Show in a Last Man Standing match after choking him out with 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 on the November 7 episode of SmackDown. Hardy defeated The Undertaker in an Extreme Rules match the following week on SmackDown due to interference from Big Show. The Undertaker then went on to defeat Show in a casket match at Survivor Series and again in a steel cage match by submission on SmackDown a week later 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 Big Show. Following this, Undertaker took another hiatus from the WWE.

After a four-month hiatus, The Undertaker returned at SummerSlam in August by attacking CM Punk, who had just won the World Heavyweight Championship from Jeff Hardy in a Tables, Ladders, and Chairs match. At Breaking Point, The Undertaker faced Punk in a submission match. The Undertaker had originally won the match with his Hell's Gate submission hold, but the match was restarted by SmackDown General Manager Theodore Long, who ruled that the ban placed on the move by Vickie Guerrero was still in effect. Punk went on to win the match with his anaconda vise when referee Scott Armstrong called for the bell, despite Undertaker never submitting in a recreation of the Montreal Screwjob, which took place in the same venue in 1997. On the September 25 episode of SmackDown, Theodore Long officially lifted the ban, after being released from a casket The Undertaker had placed him in. The feud between the two continued and at Hell in a Cell, The Undertaker won the World Heavyweight Championship from Punk in a Hell in a Cell match. The Undertaker successfully defended the title against CM Punk on the October 23 episode of SmackDown, in a fatal four-way match at Bragging Rights against Punk, Batista and Rey Mysterio and in a triple threat match against Chris Jericho and Big Show at Survivor Series. He faced Batista at TLC: Tables, Ladders & Chairs for the championship and won when the match was restarted by Long, after Batista had originally won after utilizing a low blow. The next night on Raw, Undertaker competed in a tournament to crown the 2009 Superstar of the Year, losing to Randy Orton by countout in the first round after a distraction by Orton's protegès Cody Rhodes and Ted DiBiase.

After successfully defending the World Heavyweight title against Rey Mysterio at the Royal Rumble, The Undertaker lost the championship at the Elimination Chamber pay-per-view, where a pyrotechnics malfunction momentarily engulfed The Undertaker in flames on three occasions during his ring entrance, but he was able to continue with his scheduled match, with first and second-degree burns on his chest and neck that, according to a WWE spokesman, "looked like a bad sunburn". The Undertaker lost the title to Chris Jericho after interference from Shawn Michaels; Jericho has said on multiple occasions that the pyrotechnician responsible for the accident was immediately escorted from the arena and relieved of his employment with WWE, at the behest of Calaway.

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 XXIV in 1997 and 2008 and Michaels main evented WrestleMania XII and XIV in 1996 and 1998 and XX and 23 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 at the Fatal 4-Way pay-per-view to compete for the World Heavyweight title. 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.

At SummerSlam, The Undertaker returned to confront Kane and Rey Mysterio, only to be attacked with a Tombstone Piledriver by Kane. With Kane revealed as his attacker, the two feuded for the next few months over the World Heavyweight Championship. After losing to Kane at Night of Champions, Paul Bearer returned as Undertaker's manager on the September 24 episode of SmackDown. However, Bearer turned on him at Hell in a Cell to help Kane win once again. The feud ended at Bragging Rights when The Nexus helped Kane defeat Undertaker in a Buried Alive match. Undertaker was originally booked to beat Kane for the title at Bragging Rights, but he needed surgery for a torn rotator cuff, causing him to be written off.

Final years of The Streak (2011–2014)
After the 2011 Royal Rumble, promotional videos began airing, showing The Undertaker entering and standing within a Western-style old house on a rainy desert. Each promo ended with the date 2–21–11 being "burned into" the screen. On the February 21 episode of Raw, The Undertaker returned, but before he could speak, Triple H also returned and confronted him. The two challenged each other to a match at WrestleMania XXVII, which was later made a No Holds Barred match and which The Undertaker won by submission. However, he had to be carried away from the ring on a stretcher.

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 guest 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's next TV appearance was on Old School Raw on March 4, 2013, where he opened the show by performing his signature entrance. CM Punk, Randy Orton, Big Show and Sheamus fought in a fatal four-way match to determine who would face him at WrestleMania 29, which Punk won. After the real-life death of Paul Bearer on March 5, 2013, a storyline involving Punk regularly spiting The Undertaker through displays of flippancy and disrespect towards Bearer's death began. Punk interrupted The Undertaker's ceremony to honor Bearer on Raw, stealing the trademark urn and later using it to attack Kane, humiliate The Brothers of Destruction and mock Bearer. Undertaker defeated Punk at WrestleMania 29 to extend his Streak to 21–0 and then took back the urn. The following night on Raw, Undertaker came out to pay his respects to Bearer, but was interrupted by The Shield, who attempted to attack Undertaker before Kane and Daniel Bryan made the save. Undertaker wrestled his first Raw match in three years on the April 22 episode, teaming with Kane and Bryan against The Shield in a losing effort. Four days later, he wrestled his first SmackDown match in three years, defeating Shield member Dean Ambrose by submission. Afterward, Undertaker was attacked by Ambrose and the rest of The Shield, who performed a triple powerbomb through the broadcast table on him.

On the February 24, 2014, episode of Raw, The Undertaker returned to confront Brock Lesnar and accepted his challenge for a match at WrestleMania XXX. After 25 minutes and three F-5s, Lesnar won the match by pinfall, ending The Undertaker's Streak in what was described as "the most shocking result in WWE history". Following the match, Undertaker was hospitalized with a severe concussion which he suffered in the first minutes of the match. In a December 2014 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 reasoned 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.

Post-Streak career (2015–present)
In February 2015, Bray Wyatt began a series of cryptic promos which led to Fastlane, where Wyatt challenged Undertaker to a match at WrestleMania 31, which Undertaker accepted. At the event on March 29, Undertaker defeated Wyatt after two Tombstone Piledrivers.

At Battleground in July, Undertaker made his return by attacking Brock Lesnar as Lesnar was on the verge of defeating Seth Rollins during his WWE World Heavyweight Championship match, which caused the match to end in a disqualification win for Lesnar. The next night on Raw, Undertaker explained his actions as revenge – not for Lesnar breaking The Streak, but rather the constant taunting he allowed Paul Heyman to engage in. Later that night, after Undertaker and Lesnar brawled throughout the arena and had to be separated, a rematch was scheduled for SummerSlam in August, where Undertaker controversially defeated Lesnar. Lesnar put Undertaker in a kimura lock and the timekeeper rang the bell after seeing The Undertaker supposedly indicating submission, but since the referee had not seen a submission and never stopped the match, the match continued. The confusion allowed Undertaker to surprise Lesnar with a low blow and apply Hell's Gate, in which Lesnar passed out. At Hell in a Cell, The Undertaker was defeated by Lesnar in a Hell in a Cell match after Lesnar hit him with a low blow and executed the third F-5 of the match.

While the crowd gave Undertaker an ovation after his loss to Lesnar, he was attacked and captured by The Wyatt Family (Bray Wyatt, Luke Harper, Erick Rowan and Braun Strowman), who carried him away from the ring. After ambushing and capturing Kane the next night on Raw, Wyatt explained that he had claimed their souls and stole their demonic powers. The Brothers of Destruction returned on the November 9 episode of Raw and attacked The Wyatt Family, setting up a tag team match at Survivor Series, which honored Undertaker's 25 years in WWE. At the event on November 22, The Brothers of Destruction defeated Wyatt and Harper.

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 if Shane won, he would gain control of Raw. Vince later decided that should The Undertaker lose the match against Shane, it would be his final match at WrestleMania. After weeks of mind games and physical confrontations between the pair, Undertaker defeated Shane McMahon at WrestleMania 32 on April 3. The Undertaker made his return on the 900th episode of SmackDown on November 15, issuing a threat to Team SmackDown if they failed to defeat Team Raw at the upcoming Survivor Series pay-per-view.

The Undertaker then appeared 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 returned on the March 6 episode of Raw and performed a chokeslam on Reigns. This led to a No Holds Barred match between Undertaker and Reigns at WrestleMania 33 on April 2, where Undertaker lost to Reigns after five spears in his fourth WrestleMania main event. After the match, Undertaker left his gloves, coat and hat in the center of the ring before slowly making his exit.

Undertaker took part in the Raw 25 Years episode of Raw on January 22, 2018, his first post-WrestleMania 33 appearance. In the months prior to WrestleMania 34, John Cena challenged The Undertaker to a match. At the event 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 and were struck by lightning. The Undertaker then appeared and beat Cena in an impromptu three-minute squash match. Three weeks later, The Undertaker defeated Rusev at WWE's Greatest Royal Rumble event in a casket match.

At Super Show-Down in Australia on October 6, The Undertaker faced Triple H in a no disqualification match billed as the "Last Time Ever"; they were accompanied by Kane and Shawn Michaels, respectively. The Undertaker lost the match after interference from Michaels. After the match, the four men shook hands as a sign of respect, however, Undertaker and Kane would attack them. As a result, the duos reunited their respective tag teams – The Brothers of Destruction and D-Generation X – and faced each other at Crown Jewel on November 2, where The Undertaker and Kane lost.

On the April 8, 2019, episode of Raw, the night after WrestleMania 35 – the first WrestleMania in 19 years without his involvement – The Undertaker made his next appearance, interrupting and attacking Elias during one of his musical performances. The Undertaker made his return to the ring to face Goldberg at Super ShowDown in Saudi Arabia on June 7, defeating him in the main event of the night in what was their first match against each other. On the June 24, 2019, episode of Raw, during a handicap match in which Roman Reigns was dominated by Shane McMahon and Drew McIntyre, The Undertaker suddenly appeared and attacked McMahon and McIntyre. It was later announced that Undertaker and Reigns would face McMahon and McIntyre in a No Holds Barred tag team match at Extreme Rules. At the event, Undertaker and Reigns won.

The Undertaker returned at Super ShowDown in Saudi Arabia on February 27, 2020, as a surprise replacement in a gauntlet match. He entered the match last replacing Rey Mysterio and he then defeated AJ Styles to win the Tuwaiq Trophy. On the March 2, 2020 episode of Raw, Styles taunted The Undertaker during a match with Aleister Black and at Elimination Chamber, Undertaker made another surprise appearance by attacking Styles during a rematch with Black in a no disqualification match. The following night on Raw, Styles challenged The Undertaker to a match at WrestleMania 36. Over the following weeks, Styles would continue to provoke The Undertaker, notably calling him by his real name, Mark Calaway, and bringing his wife Michelle McCool into the picture. In response, The Undertaker would cut a promo where for the first time in years, he dropped the Deadman persona, appearing in the leather jacket and bandanna of his "American Bad Ass" persona. At the event, the two fought in a secluded rural locale, in a cinematic narrative-heavy event, rather than a traditional wrestling match. Despite the assistance of Gallows and Anderson, The Undertaker would bury Styles in an empty grave to win the match.

Professional wrestling style and persona
The original Deadman character depicted him as a Western mortician dressed in a trench coat, gray-striped tie and gray-ringed, black stetson hat with gray gloves and boot spats. He was portrayed as impervious to pain, something accomplished by Calaway not selling his opponents' attacks. He was managed by Paul Bearer, who used an urn to give Undertaker supernatural powers. During his early years, he used the rendition of the Funeral march by Frédéric Chopin as his entrance theme. WWF composer Jim Johnson changed the Chopin march to create a new theme, the Graveyard Symphony.

When he made his return in 2000, he abandoned the somber mortician-themed attires, his funeral dirge ring music, allusions to the supernatural and the accompanying morbid theatrics. In place of this, he took on a biker identity, riding to the ring on a motorcycle and wearing sunglasses and bandanas to the ring. His entrance music was replaced with popular rock songs of the time, like Limp Bizkit's "Rollin' (Air Raid Vehicle)" and Kid Rock's "American Bad Ass" (from which the name of The Undertaker's new gimmick originated), though it was accompanied by the characteristic opening bell of The Undertaker's original theme.

In 2020, Undertaker started a feud with AJ Styles. Styles claimed that, in the last months, Undertaker lost his mystique because he broke kayfabe in social media and shoot interviews. At WrestleMania 36, Undertaker presented a new character called "The Unholy Trinity", a mix of the supernatural, the American Bad Ass characters and the real-life person.

For several years, Calaway has been very hermetic about his personal life, being only presented in character to maintain the mystic of the gimmick. However, during the last years of his career, he allowed himself to be seen out of character, giving interviews as Mark Calaway and filming a documentary called The Last Ride.

Legacy and reception
The Undertaker has been named one of the greatest wrestlers of all time. 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. His consecutive matches with Shawn Michaels at WrestleManias XXV and XXVI were met with critical acclaim, with both matches winning the Pro Wrestling Illustrated and Wrestling Observer Newsletter awards for Match of the Year in 2009 and 2010 respectively.

Wrestler Big Show named The Undertaker as the greatest professional wrestler of all time, while Mark Henry and WWE chairman Vince McMahon have called him their favorite. WWE Hall of Famer and former company executive, Jim Ross, said: "Without question, The Undertaker is the greatest big man in the history of wrestling... There is no greater WWE star ever than The Undertaker".

Guinness World Records Gamer's Edition recognized Undertaker as having the most consecutive victories at WrestleMania in 2016. In November 2015, Telegraph journalist Tom Fordy called The Undertaker "the world's greatest sportsman".

Undertaker's character has been praised as one of the best in professional wrestling. He received the Wrestling Observer Newsletter's Best Gimmick award from 1990 to 1994. Tim Friorvant of ESPN named The Undertaker "a character that has been a cornerstone of the WWE for more than three decades". Shawn Valentino of Pro Wrestling Torch said "The Undertaker may have been the greatest character in the history of professional wrestling".

A 12-minute match between The Undertaker and Stone Cold Steve Austin drew a 9.5 rating on June 28, 1999. It stands as the highest-rated segment in Raw history.

Reaction to later career
In contrary to this high praise, Undertaker has been criticized for continuing to wrestle after his first defeat at WrestleMania. Callaway stated that, after suffering a severe concussion against Lesnar, he lost his confidence. At WrestleMania 33, after his second defeat against Roman Reigns, Luis Paez-Pumar of Rolling Stone said that The Undertaker "should have retired when The Streak was broken", but "lived on to pass the rub on to Reigns in the sloppiest, saddest manner possible". The Undertaker himself said he was disappointed by his performance against Reigns. After his match against John Cena at WrestleMania 34, IGN posted an article titled "Undertaker's return was awesome, but now he needs to retire". After his match at Crown Jewel in November 2018, Pro Wrestling Torch's Wade Keller wrote that Undertaker looked "brittle" and Jason Powell of Pro Wrestling Dot Net said "they [Undertaker, Kane, Michaels and Triple H] need to accept their limitations, stop pretending they belong in main events, and stop acting like being in these main events isn't stealing the spotlight". His subsequent match with Goldberg at Super ShowDown in June 2019 was also widely pilloried, with Bryan Rose of the Wrestling Observer Newsletter calling it "sad more than anything". In reviewing the show, Dave Meltzer of the same publication wrote that Goldberg "has juice left, while Undertaker doesn't". The Undertaker himself called the match "a disaster".

Personal life
Calaway was married to his first wife Jodi Lynn between 1989 and 1999 and they had a son Vincent Gunner Calaway, born in 1993. Calaway married his second wife, Sara Frank, in 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 Calaway's wife. The couple had two daughters together Chasey and Gracie Calaway before divorcing in 2007. In 2010, he married former wrestler Michelle McCool and the couple's first child Kaia Faith Calaway was born in 2012.

In the 1990s, Calaway started his 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.

Calaway invests in real estate with business partner Scott Everhart. Calaway and Everhart finished construction on a $2.7m building in Loveland, Colorado, called "The Calahart" (a portmanteau of their last names). A dog-lover, Calaway and his ex-wife Sara established The Zeus Compton Calaway Save the Animals fund at the Texas A&M College of Veterinary Medicine & Biomedical Sciences to help pay for lifesaving treatments for large-breed dogs.

Calaway is a fan of boxing and mixed martial arts. He has practiced Brazilian jiu-jitsu and earned a black belt in 2011. His striking gloves and Hell's Gate submission (a modified gogoplata) were also inspired by mixed martial arts.

Calaway has made several donations to politically conservative causes and Republican candidates and has worn clothing stating opposition to the US national anthem protests.

Other media
Calaway made his film debut as Hutch in the 1991 film Suburban Commando. He had guest roles on Poltergeist: The Legacy and Celebrity Deathmatch. In 2002, Calaway appeared out of character on the Canadian sports show Off the Record with Michael Landsberg.

Calaway's WWE character has been included in numerous WWE video games, beginning with WWF Super WrestleMania (1992) and lastly in WWE 2K20 (2019). A special Undertaker-themed version of WWE 2K14 was released in 2013. Undertaker has also made the most appearances out of any wrestler, having appeared in every game in the franchise.

A short series of comic books based on The Undertaker character was published monthly by Chaos! Comics between February 1999 and January 2000. All ten issues were written by Beau Smith, with art by Manny Clark. It focused mostly on his kayfabe background and also featured such characters as Paul Bearer, Mankind and The Undertaker's half-brother Kane. The series has been collected into several trade paperbacks published by Titan Books between 2000 and 2001, titled WWF Presents: Undertaker.