The Undertaker Mark William Calaway ( March 24 , 1965 ) , better known by his ring name The Undertaker ( sometimes simply Taker ) , is an American professional wrestler signed to WWE . He is the company ' s most tenured performer , and is the only remaining active competitor from the very first episode of " WWE Raw " in 1993 . Calaway began his wrestling career with World Class Championship Wrestling ( WCCW ) in 1984 . He joined World Championship Wrestling ( WCW ) as " Mean " Mark Callous in 1989 . When WCW did not renew Calaway ' s contract in 1990 , Calaway signed with the World Wrestling Federation . After debuting as Kane the Undertaker , the name was shortened to The Undertaker and he has remained with the company since . The Undertaker has two contrasting personas : The Deadman , an undead , occult - like figure , which has consisted of many different versions , beginning with the Western mortician character in November 1990 and ending with the Satanic Ministry of Darkness leader in September 1999 before returning to The Deadman in March 2004 as a hybrid of all his previous incarnations . His other persona is The American Bad Ass , a biker which ran from May 2000 to November 2003 . Because of his gimmicks , Undertaker has a number of specialty matches associated with him : the Casket match , the Buried Alive match , the Hell in a Cell and the Last Ride match . An important part of the character is his half - brother Kane , who was introduced in October 19 97 and with whom he has both feuded and teamed as the Brothers of Destruction . The Undertaker had an undefeated streak at WrestleMania of 21 - 0 before losing to Brock Lesnar at WrestleMania 30 . His record at WrestleMania currently stands at 22 - 1 . Among other accolades , Calaway is an eight - time World Champion having won the WWF / E Championship four - times , the World Heavyweight Champion three - times , as well as the USWA Unified World Heavyweight Championship one - time under the Master of Pain character . The Undertaker is also a seven - time World Tag Team champion : a six - time WWF Tag Team Champion and one - time WCW Tag Team Champion . The Undertaker was the winner of the 2007 Royal Rumble and became the first man to enter the annual event last and win . Calaway is also the only current WWE wrestler to have appeared on the first episode of its " Raw " program . Career history . Early career ( 1984 – 1990 ) . Calaway made his debut in 1984 in the Dallas , Texas - based World Class Championship Wrestling ( WCCW ) under the ring name " Texas Red " . He wrestled and lost his first match against Bruiser Brody . In 1988 , after four years in the promotion , he left . After leaving WCCW , Mark joined the CWA ( which became the USWA after Jerry Jarrett merged CWA with WCCW ) and wrestled under several gimmicks . On April 1 , 1989 , he was booked to win his first professional wrestling title , the USWA Unified World Heavyweight Championship , defeating Jerry " The King " Lawler , under the stage name " The Master of Pain " . While performing as the " The Punisher " , Calaway won the WCWA Texas Heavyweight Championship on October 5 , 1989 when Eric Embry forfeited the title . His first mainstream exposure was in World Championship Wrestling ( WCW ) . While there , he was known as " Mean " Mark Callous and wrestled as part of the Skyscrapers tag team along with " Dangerous " Dan Spivey managed by Teddy Long . During his time in the Skyscrapers , he and Spivey were involved in a feud with the Road Warriors , but Spivey left before the feud came to an end . Calaway then took on the guidance of Paul E . Dangerously and muscled his way through Brian Pillman and Johnny Ace . His most famous match in WCW was against Lex Luger for the NWA United States Championship at The Great American Bash , which he lost when Luger pinned him after a clothesline . WCW declined to renew Calaway ' s contract , after losing his last match to Sting on September 1 , 1990 at a house show . Calaway then briefly wrestled in New Japan Pro Wrestling as Punisher Dice Morgan and in October 19 90 , he signed with the World Wrestling Federation ( WWF ) . 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 . Debut and WWF Championship ( 1990 – 1991 ) . Calaway made his WWF debut as " Cain the Undertaker " at WWF Survivor Series on November 19 , 1990 . Approximately one minute into the match , Undertaker eliminated Koko B . Ware with his signature maneuver , the Tombstone Piledriver . He also eliminated Dusty Rhodes before being counted out . Shortly after Survivor Series , " Cain " was dropped from his name , and he was called simply The Undertaker . The appearance of Undertaker was modeled after a mortician from old Western movies , with the gimmick that he was impervious to pain and possessed supernatural powers , such as teleportation and manipulation of flames and lightning . It was at this time that the Undertaker switched managers from Brother Love to Paul Bearer . He made his WrestleMania debut at WrestleMania VII , squashing " Superfly " Jimmy Snuka . The win was the first in his undefeated streak at the event . After a year of battles with the Ultimate Warrior in body bag matches , Randy Savage , and Hulk Hogan , he defeated Hogan to win his first WWF Championship at Survivor Series . WWF President Jack Tunney ordered a rematch for This Tuesday in Texas six days later , where Undertaker dropped the title back to Hogan . Early feuds ( 1992 – 1995 ) . After Undertaker ' s ally Jake " The Snake " Roberts lost a match to Randy Savage on the February 8 , 1992 edition of Saturday Night ' s Main Event , Roberts tried to attack Savage ' s manager / wife Miss Elizabeth with a steel chair when the Undertaker stopped him , turning him face . The Undertaker defeated Roberts at WrestleMania VIII . He then feuded extensively with wrestlers managed by Harvey Wippleman throughout 1992 and 1993 , most notably Kamala , whom he faced and defeated in the first televised coffin match in WWF history at Survivor Series , and Giant Gonzales , whom he defeated by disqualification at WrestleMania IX and by pinfall at SummerSlam . In November 1993 , he challenged then - WWF Champion Yokozuna to a casket match at the Royal Rumble . At the Royal Rumble , Yokozuna sealed Undertaker in the casket with the assistance of several other heel wrestlers , winning the match . The Undertaker ' s " spirit " appeared from inside the casket on the video screen , warning that he would return . This began Undertaker ' s first hiatus . In reality , he had a back injury that was getting worse and needed time off . After WrestleMania X , Ted DiBiase introduced the Undertaker back to the WWF . This Undertaker , however , played by Brian Lee , was dubbed " Underfaker " later on by the fans and led to the return of the original Undertaker ( this time appearing as a zombie version of his original persona , and now wearing purple gloves and boot covers ) , and a battle at SummerSlam between the two , where the real Undertaker won the match after three Tombstone Piledrivers . At Survivor Series , Undertaker had a rematch against Yokozuna , once again in a casket match , with Chuck Norris as a special guest enforcer to keep anyone from interfering in the match . While King Kong Bundy and Bam Bam Bigelow distracted Norris , Irwin R . Schyster interfered in the match ; despite this , the Undertaker won the match by delivering a running big boot to Yokozuna , which pushed Yokozuna into the casket , and then closed the lid . Throughout most of 1995 , the Undertaker feuded with members of Ted DiBiase ' s Million Dollar Corporation . At WrestleMania XI , while Undertaker was facing King Kong Bundy , Kama Mustafa stole the Undertaker ' s source of storyline power , the urn , and disrespected the Undertaker by melting it into a large gold necklace . As part of the angle , the two faced each other in a casket match at SummerSlam , which the Undertaker won . Several weeks later , Undertaker injured his orbital bone near his eye , forcing a period of absence for surgery , until his return at Survivor Series . Lord of Darkness , Ministry of Darkness ( 1996 – 1999 ) . The Undertaker returned at the 1995 Survivor Series , wearing a Phantom - like ghostly Grey upper facemask . At the Royal Rumble , the Undertaker was unmasked in a WWF Championship match against Bret Hart . Diesel interfered in the match to cost the Undertaker the championship , and one month later , while Diesel was facing Hart in a steel cage match , Undertaker came up from under the ring to drag Diesel underneath , allowing Hart the victory . This feud culminated in a match between the duo at WrestleMania XII , in which the Undertaker was victorious . His next feud commenced the very next night , when Mankind made his debut , interfering in the Undertaker ' s match with Justin Hawk Bradshaw . For the next few months , Mankind ambushed and cost the Undertaker several matches . The Undertaker faced Mankind for the first time in a match at the King of the Ring , which Mankind won . The feud intensified , and they began taking their battles into crowds , backstage areas , and in the boiler rooms of different arenas . As a result , the first ever Boiler Room Brawl match was booked between the two at SummerSlam . During the match , when Undertaker reached for his urn , Paul Bearer hit him with it , turning on the Undertaker and allowing Mankind to " incapacitate " The Undertaker 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 at In Your House : Buried Alive . Undertaker won the match after a Chokeslam into the open grave , but after interference from The Executioner , as well as the help of several other superstars , The Undertaker was ultimately " Buried Alive " . As a result , a match was booked for the upcoming Survivor Series , again pitting The Undertaker against Mankind , with a unique stipulation . Hanging 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 Undertaker won the match , interference from The Executioner enabled Bearer to escape the Undertaker ' s clutches . The Undertaker then shifted feuds and briefly turned his attention to The Executioner , who had become a thorn in his side since his arrival . At In Your House : It ' s Time , the Undertaker defeated The Executioner in an Armageddon rules match . By the end of 1996 , the Undertaker began a feud with Vader , culminating in a loss to Vader at the Royal Rumble after Bearer interfered on behalf of his new protégé . After this loss , the Undertaker ' s character began to focus his attention on the WWF Championship . At WrestleMania 13 , The Undertaker defeated Sycho Sid to win the WWF Championship for the second time in a No Disqualification match . After the event , Paul Bearer attempted to rejoin with the Undertaker , using the threat of revealing ' Taker ' s " biggest secret " . In the storyline , Bearer announced that Undertaker was a murderer , who as a child had burned down the family funeral home business ( where Bearer worked ) , killing his parents and his younger brother . Undertaker claimed there was no way for Bearer to have that information , but Paul announced that he was told this by Undertaker ' s brother Kane , who was still alive but horribly burned and scarred . Bearer raised Kane after the fire , having him institutionalized . Now , Kane was waiting for revenge after all these years . In defense , Undertaker responded that Kane , a pyromaniac , had been the one to set the fire and could not have possibly survived . His next major storyline began at SummerSlam in 1997 when referee Shawn Michaels accidentally hit Undertaker with a steel chair shot meant for Bret Hart , costing the Undertaker his WWF Championship . Although the chair shot was accidental , Michaels taunted the Undertaker in the following weeks . The feud culminated at In Your House : Badd Blood , where the Undertaker challenged Michaels to the first ever Hell in a Cell match . During this match , Undertaker ' s storyline brother Kane made his debut , ripping off the door to the cell and giving Undertaker a Tombstone Piledriver , Undertaker ' s trademark finisher , allowing Michaels to pin him . As the angle progressed , Kane , with Paul Bearer , challenged the Undertaker to fights , but the Undertaker consistently refused to fight his brother . The Undertaker ' s final encounter with Michaels was in the return of the casket match at the Royal Rumble , where Kane cost the Undertaker the win by trapping him in the coffin , padlocking the casket lid , and setting it ablaze . The Undertaker , however , had disappeared when the casket lid was reopened . After a two - month hiatus , Undertaker returned to continue the angle and defeat Kane at WrestleMania XIV . The two had a rematch , the first ever Inferno match , one month later at In Your House : Unforgiven , where The Undertaker was booked to win by setting Kane ' s right arm on fire . Undertaker ' s longtime feud with Mankind was renewed afterwards , when Mankind cost the Undertaker a number one contenders match against Kane . As a result , Undertaker and Mankind faced each other in a Hell in a Cell match at King of the Ring . During the match , Undertaker threw Mankind off the roof of the sixteen foot cell onto the Spanish announcers ' table below , in what was a preplanned move . He later chokeslammed Mankind through the roof of the cell into the ring — which legitimately knocked Mick Foley ( Mankind ) unconscious — and finished the match by chokeslamming Mankind onto a pile of thumbtacks . In July at Fully Loaded , Undertaker and Steve Austin were booked to defeat Kane and Mankind to win the WWF Tag Team Championship . Undertaker and Austin ' s reign as tag champions lasted for only two weeks , as Kane and Mankind regained the titles on an episode of Raw . Undertaker then became the number one contender for the WWF Championship at SummerSlam , now held by Austin . Shortly before SummerSlam , however , Undertaker revealed that he and Kane were working together as brothers . Despite this revelation , Undertaker told Kane that he did not want him to interfere in the match with Austin , and even though Undertaker lost the match , he handed Austin his belt back after the match in a show of respect . In September , the storyline continued , and Undertaker began to show heel characteristics , becoming a tweener , when he and Kane revealed the fact that they were in cahoots to rid Austin of his title for Vince McMahon . At Breakdown : In Your House , Undertaker and Kane were booked in a triple threat match with Austin for his WWF title ; McMahon stated that the brothers were not allowed to pin each other . Undertaker and Kane pinned Austin simultaneously after a double chokeslam , so the title was vacated by McMahon . This led to a match at In Your House : Judgment Day between the two brothers for the title , with Stone Cold 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 Undertaker with , but as Kane had his back turned , both Bearer and Undertaker hit Kane with the chair . Undertaker went for the pin , but Austin refused to count the fall , attacked the Undertaker , and counted out both brothers . Finally , Undertaker turned heel the next night on Raw is War for the first time in over six years , reconciling with Paul Bearer and claiming that he and Bearer would unleash their Ministry of Darkness on the World Wrestling Federation . As part of this new angle , he admitted that he had indeed set the fire that killed his parents , for which he had previously blamed Kane . After Survivor Series , Undertaker returned his attention back to his previous feud with Austin for having costing him the title at Judgment Day , viciously 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 angle , McMahon scheduled a Buried Alive match between Undertaker and Austin in December 1998 at Rock Bottom : In Your House . In the weeks leading up to Rock Bottom , the Undertaker character became increasingly demonic and satanic , attempting to embalm Austin alive , trying to have Kane committed to a mental asylum , and having his druids chain Austin to his symbol and raising it high into the arena . Undertaker , however , lost the match after Kane interfered . In January 1999 , Undertaker returned , remaining a monster heel and forming the Ministry of Darkness , explaining that he was taking orders from a " Higher Power . " Eventually , the Ministry merged with Shane McMahon ' s Corporation heel stable to form the Corporate Ministry . During this time , The Undertaker was booked to defeat Austin for his third WWF Championship at Over the Edge with help from Shane McMahon , the special referee . Two weeks later , it was revealed on Raw that Vince McMahon had been the Undertaker character ' s " Higher Power " all along . After Undertaker dropped the WWF title back to Austin one night after King of the Ring , and lost a First Blood match at Fully Loaded , his relationship with the McMahons dissolved and the Corporate Ministry disbanded . Undertaker then began a storyline where he teamed with The Big Show in a tag team known as The UnHoly Alliance , which held the WWF Tag Team Championship twice . He was then scheduled to perform at Unforgiven , contending for the WWF Championship , but a groin injury knocked him out of action for the remainder of the year and part of the next . Onscreen , his absence was explained by The Undertaker quitting . American Bad Ass / Big Evil ( 2000 – 2003 ) . Undertaker was due to return to action for WrestleMania 2000 , but a legitimate biceps injury in February 2000 delayed his return until May 2000 . When he returned at Judgment Day , Undertaker ' s gimmick was dramatically modified in line with the WWF ' s change to a more realistic approach . His gimmick became that of an intimidating biker , known as the " American Bad Ass " , and he began using the Last Ride Elevated Powerbomb as his finishing move , as opposed to the Tombstone Piledriver , which had become synonymous with the Undertaker over the years . Upon his return , his storyline called for him to take out all the members of the McMahon - Helmsley Faction , which quickly turned him face again . He also targeted their leader , WWF Champion Triple H . At King of the Ring , Undertaker teamed with The Rock and Kane to defeat the team of Triple H , Shane McMahon , and Vince McMahon . Afterwards , he was booked to team with Kane to contend for the WWF Tag Team Championship . They defeated Edge and Christian , earning the right to face them the following week for the tag titles , which Edge and Christian retained . Kane turned on The Undertaker by chokeslamming him twice on the August 14 episode of Raw . This 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 . Undertaker was then booked to challenge Kurt Angle for the WWF Championship at Survivor Series . Angle , however , defeated Undertaker following interference from Kurt ' s real life brother Eric Angle . Undertaker demanded and was awarded a spot in the Six - Man Hell in a Cell match for the WWF Championship at Armageddon . Undertaker did not win the match , but did perform a move where he threw Rikishi off the roof of the cell . In 2001 , Undertaker reunited with Kane as the Brothers of Destruction , challenging for the WWF Tag Team Championship once again . As part of the angle , they received a shot at the title at No Way Out , facing Edge and Christian and then - champions the Dudley Boyz in a Tables Match . The Brothers of Destruction dominated almost the entire match but were not the winners . Undertaker was then booked to defeat Triple H at WrestleMania X - Seven , where he improved his WrestleMania winning streak to 9 - 0 . He and Kane continued a storyline that focused on Triple H , who formed a " surprise alliance " with WWF Champion Steve Austin . The Brothers of Destruction were granted an opportunity to face Triple H and Austin for their titles . After Undertaker and Kane acquired the WWF Tag Title from Edge and Christian , Triple H pinned Kane after attacking him with a sledgehammer at Backlash , where the Brothers of Destruction dropped the titles . With Kane injured , Undertaker feuded briefly Steve Austin for his WWF Championship , but at Judgment Day , Austin retained his title against the Undertaker . As part of the 2001 The Invasion angle , The Undertaker ' s next nemesis was Diamond Dallas Page , who was obsessively following The Undertaker ' s wife Sara . At SummerSlam , WCW Tag Team Champions Undertaker and Kane defeated Page and his partner Chris Kanyon in a steel cage match to win the WWF Tag Team Championship . At Survivor Series , Undertaker began a storyline where he took on The Alliance ' s Steve Austin , Booker T , Rob Van Dam , Shane McMahon , and Kurt Angle while teaming up with Kane , the Rock , Chris Jericho , and The Big Show . Angle pinned the Undertaker due to interference by Austin . After the Alliance was defeated , The Undertaker turned heel once again by forcing commentator Jim Ross to kiss Vince McMahon ' s ass . 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 was booked to defeat Van Dam to capture the WWF Hardcore Championship . Undertaker ' s next angle began at the Royal Rumble in 2002 when Maven eliminated him by dropkicking him 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 The Undertaker . The Undertaker responded by costing The Rock the number one contendership for the WWF Undisputed 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 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 . 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 angle with Flair , Undertaker defeated Steve Austin at Backlash to win the number one contendership for the WWF Undisputed Championship . Later that night , his storyline called for him to help Hulk Hogan win his title match against the Undisputed Champion Triple H . The Undertaker was then booked to defeat Hogan for his fourth world championship at Judgment Day . Undertaker soon turned face after a ladder match with Jeff Hardy , whose hand he raised after the match as a sign of respect . Undertaker , however , dropped the title at Vengeance to The Rock in a Triple Threat match that also involved Kurt Angle . The Undertaker was then switched from Raw to SmackDown ! , alongside former Raw talent Brock Lesnar , Chris Benoit , and Eddie Guerrero . Undertaker was booked to challenge Lesnar in a title match at Unforgiven that inevitably ended in a double - DQ . Their feud carried over to No Mercy in a Hell in a Cell match . Undertaker performed in the match with a legitimate broken hand and eventually lost to the champion . Undertaker took a leave from wrestling after the Big Show threw him off the stage in Memphis , sparking a feud ( in reality , he and his wife , Sara , were expecting their first child together ) . The Undertaker returned at the Royal Rumble in 2003 . He immediately continued his feud with Big Show and defeated him via submission at No Way Out with a triangle choke . A - Train entered the angle by attempting to attack Undertaker after the match , but Nathan Jones came to his aid . The storyline resumed as 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 . Jones , however , was removed prior to the match , making it a handicap match , which Undertaker won with the help of Jones . Over the remainder of the year , he 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 . The second , at No Mercy , was a Biker Chain match between Undertaker and Lesnar , which Lesnar won with the help of Vince McMahon . This resulted in a storyline feud with McMahon , culminating at Survivor Series where Undertaker lost a Buried Alive match against McMahon when Kane interfered . The Undertaker disappeared for some time following the match , with Kane claiming that he was " dead and buried forever . " Return of the Deadman ( 2004 – 2006 ) . In the storyline leading up to WrestleMania XX , Kane was haunted by vignettes proclaiming an Undertaker return . The first was during the Royal Rumble when Undertaker ' s bells tolled , distracting Kane and allowing Booker T to eliminate him . At WrestleMania XX , the Undertaker , accompanied by Paul Bearer and in his " Deadman " persona , returned and defeated Kane . Three months later , Bearer was kidnapped by the Dudley Boyz at the direction of Paul Heyman , who then took " control " of Undertaker . The angle added a new twist at The Great American Bash where Undertaker was forced to fight a handicap match against the Dudleys , and if he lost , Heyman would bury Bearer in cement . The Undertaker won but buried Bearer anyway , explaining that Bearer was merely a liability now and that he had no use for him anymore . Fans were later told that Bearer was " seriously injured , " but in reality , he was simply removed from WWE programming due to health reasons . The Undertaker also remained a face . After defeating the Dudley Boyz , Undertaker began a new storyline feud by challenging then WWE Champion John " Bradshaw " Layfield ( JBL ) to a title match at SummerSlam , which Undertaker lost when he disqualified himself . At No Mercy , Undertaker and JBL were booked to compete in the first ever " Last Ride " match , although Undertaker lost after Heidenreich interfered . After a brief program with Heidenreich , 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 , in which Undertaker was unsuccessful , again due to Heidenreich ' s interference . This led to a Casket match between Undertaker and Heidenreich at the Royal Rumble , where Undertaker sealed Heidenreich in a casket for the victory to end the storyline . Soon afterward , Randy Orton challenged The Undertaker to a match at WrestleMania 21 , in an angle where Orton claimed that he would end The Undertaker ' s WrestleMania winning streak . Even with help from his father " Cowboy " Bob Orton , Randy failed , and the Undertaker improved his WrestleMania record to 13 - 0 . Following WrestleMania , Undertaker took a two - month hiatus from wrestling after the birth of his second daughter in late May 2005 . He returned for the June 16 episode of SmackDown ! but lost to JBL , thanks to interference from Randy Orton . After The Great American Bash , Undertaker became number one contender to the World Heavyweight Championship , a position that JBL felt he should have . As part of the feud , on the following SmackDown ! , Undertaker lost a number one contender match against JBL , once again due to interference from Orton . With this , Undertaker resumed his feud with Orton . At SummerSlam , Orton defeated Undertaker in a WrestleMania rematch . The storyline intensified as the two taunted each other with caskets , leading to a casket match at No Mercy , in which Undertaker lost to Randy and his father " Cowboy " Bob Orton . After the match , the Ortons poured gasoline on the casket and set it afire . When the charred casket was opened , however , Undertaker had once again vanished . He returned at the Survivor Series , emerging from a burning casket . Undertaker returned to SmackDown ! in early December to haunt Orton and set up a Hell in a Cell match at Armageddon . After winning the match , Calaway took a short hiatus from wrestling , presumably due to controversy associated with the match , as Bob Orton was diagnosed with hepatitis but was allowed to bleed during the match without Calaway knowing of his condition . In early 2006 at the Royal Rumble , Undertaker returned during Kurt Angle ' s celebration of his world title defense against Mark Henry on a horse - drawn cart , signaling for a title shot . As part of their storyline feud , Undertaker lost his match with Angle at No Way Out after a thirty - minute bout . Undertaker cornered Angle after the match , and after a stare down , told Angle that he had his number and that he was not finished with him yet . The Undertaker had his No Way Out rematch for the World Heavyweight Championship against Angle on " SmackDown ! " when Henry attacked Undertaker from behind , costing him the title . This began an angle between the duo , as Undertaker then challenged Henry to a Casket match at WrestleMania 22 , and Henry , like Orton a year before him , vowed to end Undertaker ' s WrestleMania winning streak . Undertaker defeated Henry to become 14 - 0 at WrestleMania , keeping his storyline undefeated streak alive . During a rematch on the next edition of SmackDown ! , The Great Khali made his debut and assaulted the Undertaker , signaling the end of one storyline and the beginning of a new one . The Undertaker was not heard from until the May 5 edition of SmackDown ! , as Theodore Long delivered a challenge from Undertaker to Khali for a match at Judgment Day . Undertaker was booked to cleanly lose to Khali , and he did not appear again until the July 4 edition of " SmackDown ! " to accept Khali ' s challenge to a Punjabi Prison match at The Great American Bash . Khali , however , was removed from the match due to elevated liver enzymes and was replaced by ECW Champion The Big Show , over whom The Undertaker gained the victory . In the storyline , Teddy Long replaced Khali with Big Show as punishment for an attack on Undertaker shortly before the match . Khali was then challenged to a Last Man Standing match at SummerSlam after interfering in Undertaker ' s match with World Heavyweight Champion King Booker . Khali refused the challenge for SummerSlam , though Long made the match official for the August 18 episode of SmackDown ! instead . Undertaker won the match by striking Khali with the steel stairs , delivering several chair shots , and finishing him with a chokeslam . The Undertaker ' s next match was with WWE United States Champion Mr . Kennedy at No Mercy but was disqualified in the match after he hit Kennedy with the championship belt . On the November 3 edition of SmackDown ! , Undertaker reunited with Kane to form the Brothers of Destruction for the first time in five years , defeating the reluctant opposition team of Mr . Kennedy and Montel Vontavious Porter , with whom Kane was feuding with at the time . As part of the angle , Kennedy defeated Undertaker in a First Blood match at Survivor Series after interference from MVP , but finally defeated Kennedy in a Last Ride match at Armageddon by delivering a chokeslam and Tombstone on the roof of the hearse , sticking him in the back , and driving the hearse out of the arena . The two continued to feud into 2007 as Kennedy cost Undertaker two World Heavyweight Championship opportunities for a championship match at the Royal Rumble . World Heavyweight Champion / Pursuit of the World Heavyweight Championship ( 2007 – 2010 ) . Undertaker won his first Royal Rumble match after Shawn Michaels attempted Sweet Chin Music , and Undertaker ducked and lifted Michaels over the top rope for the victory . He became the first man to enter the Rumble at number 30 and win the match . He then began an angle with Batista , whom he defeated at WrestleMania 23 to win his first World Heavyweight Championship . On the next SmackDown ! , Batista entered the ring and declared that he wanted a rematch in the form of a Last Man Standing match at Backlash . The rematch ended in a draw when neither man was able to answer the ten - count after Batista speared Undertaker off the entrance stage , causing the steel pillars to fall on top of the two men , resulting in the Undertaker retaining the Championship . On the May 11 SmackDown ! taping , Undertaker had a Steel Cage match with Batista that was booked to result in a draw when both men ' s feet touched the floor at the same time . After the match , Mark Henry returned and assaulted the defenseless Undertaker . Immediately after the assault , Edge cashed in his Money in the Bank title shot , and Undertaker dropped the World Heavyweight Championship to Edge . As Undertaker laid in the ring , druids appeared and carried him to the backstage area . In reality , Calaway had suffered an arm injury that required surgery , but WWE did not want to break the Undertaker ' s character by having him forfeit the title . During Calaway ' s rehabilitation , Henry squashed local jobbers and bragged about his assault on Undertaker , until vignettes began playing promoting Undertaker ' s return . The Undertaker returned at Unforgiven , successfully defeating Henry with a Last Ride from the corner and again on SmackDown ! two weeks later with a chokeslam . Batista and Undertaker re - ignited their storyline feud at Cyber Sunday where the fans chose guest referee Steve Austin , but Batista retained the world title after two Batista Bombs . They battled again inside Hell in a Cell at Survivor Series where Edge returned and interfered by giving Undertaker a con - chair - to and pulling an unconscious Batista on top of Undertaker for the pinfall to retain the World Heavyweight Championship . In response to this , Undertaker delivered a Tombstone piledriver to General Manager Vickie Guerrero , on the next SmackDown ! , in storyline , sending her to the hospital . Returning Assistant - GM Theodore Long declared a Triple Threat match for the title at Armageddon . Edge won the match by pinning Batista , who had been given a Tombstone piledriver which was followed by Undertaker being hit with a chair while he attempted the pinfall . At No Way Out 2008 , Undertaker defeated Batista , Finlay , The Great Khali , Montel Vontavious Porter , and Big Daddy V in a SmackDown / ECW Elimination Chamber , to become the number one contender for Edge ' s World Heavyweight Championship at WrestleMania XXIV . He defeated Edge at WrestleMania with his gogoplata submission hold , to win his second World Heavyweight title and elevate his undefeated streak at WrestleMania to 16 - 0 . In a WrestleMania rematch , The Undertaker defeated Edge once again at Backlash to retain the World Heavyweight Championship . The Undertaker battled Edge for the title at Judgment Day , which he won but could not keep the title because of the count out victory . The two faced each other again for the championship at One Night Stand in a Tables , Ladders , and Chairs match , which Undertaker lost . As a result of the storyline stipulation , Undertaker was banished from WWE . On the July 25 , 2008 episode of Friday Night SmackDown , Vickie Guerrero announced that Edge would face the Undertaker at SummerSlam in a Hell in a Cell match , 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 to make 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 , the 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 the Big Show knocked the Undertaker out with a punch to the back of Undertaker ' s head . At Cyber Sunday the Undertaker defeated the Big Show in a Last Man Standing match after applying Hell ' s Gate . The Undertaker then went on to defeat the Big Show at Survivor Series in a casket match . John " Bradshaw " Layfield declared on the February 16 edition of Raw that he wanted to make history by defeating the Undertaker at WrestleMania XXV . However , Shawn Michaels , wanted to accomplish the same feat . The following week , Michaels defeated JBL to gain the opportunity to face the Undertaker at WrestleMania . However , SmackDown GM Vickie Guerrero announced Michaels had to defeat Kozlov to face the Undertaker . On the March 2 edition of Raw , Michaels defeated Kozlov and gained the opportunity to face Undertaker at WrestleMania . Before WrestleMania XXV , Michaels teamed with Undertaker to take down both JBL and Kozlov . After winning by planting the Sweet Chin Music and tagging in Undertaker when he was clearly winning , HBK then supposedly fled from the Undertaker backstage and emerged moments later when the Undertaker ' s back was turned and delivered Sweet Chin Music again . In the days leading up to WrestleMania XXV , HBK attempted to , in his words , " Get inside the head of the Undertaker " by visiting the graves of Undertaker ' s fallen foes in WrestleManias gone by and stopping at a grave marked 16 - 1 . After explaining his view on the grave and what it represented , HBK superkicked the headstone into the grave and covered it with dirt . He finished his taunting by saying that the Undertaker ' s streak would " Rest . . . In . . . Peace . . . " . The Undertaker was visibly less than pleased with the desecration of his sanctuary and targeted HBK over the following days . One night , after a match , HBK came out and confronted the Undertaker . After a long discussion , Shawn said that although he respected Undertaker , he didn ' t fear him . A black hearse pulled up to the outside of the RAW building one night and a casket was pulled out . The Undertaker ' s theme music was audible but HBK emerged from the coffin and said " You were expecting someone else ? " . Later on , HBK explained that the coffin wasn ' t for him but rather for the Undertaker ' s streak . The Undertaker emerged moments later to find the stage , which was made up to look like a funeral , devoid of HBK . Upset that HBK escaped him again , Undertaker destroyed everything but paused and approached the coffin and opened it but to his surprise , there was no HBK . He turned away from the coffin and HBK emerged and hit the Undertaker with Sweet Chin Music before leaving again . HBK ' s final act before WrestleMania XXV was a parody of Undertaker ' s entrance in which all that was associated with the Undertaker was white which represented good and pure things . HBK approached the ring and removed a white hat and instead of a scowl , a grin was upon the face of the Showstopper . Upon entering the ring , Shawn recited Genesis and compared him and the Undertaker to day and night , respectively . After his speech , Shawn ' s music played and he started to remove his clothes before the Undertaker grabbed him and attempted to punish him . Shawn escaped again while the Undertaker steamed in anger . Upon arrival to WrestleMania XXV , Undertaker and Shawn Michaels participated in a long overdue fight . After an extremely long match , the Undertaker emerged as the victor by using the Tombstone piledriver and pinning HBK , netting the Deadman victory # 17 . As a result of CM Punk winning the World Heavyweight Championship The Undertaker made his return to Summerslam 2009 Chokeslaming Cm Punk . He would go on to defeat CM Punk for the World Heavyweight Championship at Hell in a Cell . He defeated Rey Mysterio , Batista and CM Punk again to retain his title at Bragging Rights . He defeated Chris Jericho with help from his brother , Kane . He teamed with John Cena to defeat DX and Jerishow on the November 16 , 2009 airing of Monday Night RAW , but turned on him right after the match . He defeated Jeri - Show to retain his World championship at Survivor Series , and retained it against Batista at TLC . Shawn Michaels challenged Undertaker to a Wrestlemania rematch at WrestleMania XXVI but declined . He bested Rey Mysterio in a good match - up to hold on to the belt in a match where he was bleeding from the nose and mouth , but lost to Chris Jericho at the Elimination Chamber , due to Shawn Michaels interference . On the February 22 , 2010 edition of RAW , Undertaker changed his decision about the Wrestlemania rematch against HBK and accepted the challenge , on the stipulation that if Shawn Michaels loses he loses his career . The match was later made into a no disqualification , no countout match as well . As WrestleMania , The Undertaker defeated Michaels in a " Streak vs . Career " match at WrestleMania XXVI , to extend his WrestleMania winning streak to 18 – 0 and force Michaels to retire . After the match , the Undertaker shook Michaels ' hand as a sign of respect . On the April 19 , 2010 edition of RAW , the Undertaker returned to face World Heavyweight Champion Jack Swagger , who had issued an open challenge moments before . Despite being dominated for a portion of the match , the Undertaker defeated Swagger with a Tombstone Piledriver . Undertaker had an official return to Smackdown on 25 May ( Aired on the 28th May ) and faced Rey Mysterio to qualify for the World Championship match at Fatal 4 Way . Undertaker defeated Rey Mysterio with a Tombstone Piledriver . On 1 June ( Aired 4 June ) it had been confirmed Undertaker had been brutally attacked by an unknown assailant over the weekend and is unable to compete for Fatal 4 Way . Rey Mysterio won a battle royal to replace Undertaker ' s spot in Fatal 4 Way . After a four - month absence , 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 ( reminiscent of the Montreal Screwjob , which took place in the same venue in 1997 ) . On the September 25 episode of SmackDown , Theodore Long announced that the ban had now been officially lifted , after being released from a casket that The Undertaker had apparently placed him in . The feud between the two continued and at the Hell in a Cell pay - per - view , The Undertaker won the World Heavyweight Championship from Punk in a Hell in a Cell match . The Undertaker went on to successfully defend the title against CM Punk in a rematch on " SmackDown " , in a fatal four way match at Bragging Rights , and in a triple threat match at Survivor Series . He faced Batista at for the championship , and won when the match was restarted by Long , after Batista had originally won after utilising a low blow . He later retained the championship against Rey Mysterio at the Royal Rumble in January 2010 . At the Elimination Chamber pay - per - view , a pyrotechnics malfunction momentarily engulfed The Undertaker in flames during his ring entrance . He was able to continue with his scheduled match , with a burn on his chest that " looked like a bad sunburn " according to a WWE spokesman . He lost the World Heavyweight Championship to Chris Jericho after interference from Shawn Michaels . Like the Raw Champion who also lost his world title at the Elimination Chamber ( Sheamus ) Undertaker never used the rematch clause that would normally be given to him . The following night , on " Raw " , Michaels claimed that he cost The Undertaker his championship because he wanted to face The Undertaker at WrestleMania XXVI , but The Undertaker had previously turned down his offer of a match . The Undertaker agreed to the match on the condition that Michaels ' career was on the line . The match was later made into a no disqualification , no countout match as well . At WrestleMania , The Undertaker defeated Michaels in a " Streak vs . Career " match at WrestleMania XXVI , to extend his WrestleMania winning streak to 18 – 0 and force Michaels to retire . After the match , the Undertaker shook Michaels ' hand as a sign of respect . After a hiatus ( during which he appeared twice on Raw , defeating Jack Swagger and Edge ) , he returned to " SmackDown " on May 28 , defeating Rey Mysterio to qualify for a spot in the Fatal 4 - Way pay - per - view along with Big Show and CM Punk also vying for the World Heavyweight title held by Swagger ( obtained by cashing in his Money in the Bank contract from the WrestleMania Money in the Bank ladder match on an injured Jericho ) . During the match , however , The Undertaker suffered a concussion , broken orbital bone and broken nose . He was visibly bleeding profusely on camera by the end of the match . On the June 4 , 2010 taping of SmackDown , it was reported that The Undertaker was found by his brother Kane to be " in a vegetative state " ( kayfabe ) over Memorial Day Weekend , thus unable to compete in the Fatal 4 - Way . Rey Mysterio replaced the Undertaker in the match , by winning a Battle Royal including the whole SmackDown roster and went on to win the championship . At the Money in the Bank event , Kane cashed in his Money in the Bank contract ( which he won the same night ) against Mysterio , who just defended his title against Jack Swagger , and became the new World Heavyweight Champion . Meanwhile , Kane accused various superstars of being the culprits behind his brother ' s assault , including the Straight Edge Society and Jack Swagger . Eventually , Kane declared that Mysterio was the culprit . On the August 6 , 2010 episode of SmackDown , however , Rey Mysterio declared himself innocent before claiming that Kane himself was the perpetrator behind the assault on the Undertaker . Following this accusation , Kane became visibly upset , falling to his knees and repeatedly saying to himself , " I love my brother " . At SummerSlam , the Undertaker returned to confront Kane and Rey Mysterio , only to be overpowered and tombstoned by Kane , who was revealed to be the Undertaker ' s attacker . This was the third year in a row that the Undertaker made a return at the Summerslam event . On the September 3 edition of Smackdown , Kane challenged The Undertaker to a match at Night of Champions for the World Heavyweight Championship . Kane said that the Undertaker was weaker than his former self and that Kane would finish him off . At Night of Champions , the Undertaker was indeed defeated by Kane who retained the World Heavyweight Championship by delivering a Tombstone to Undertaker in a No Holds Barred match . On the September 24 episode of Smackdown , after Kane issued a challenge to his brother to a Hell in a Cell match at the pay - per - view event with the same name , a casket was rolled to the ring at the end of Smackdown and Paul Bearer emerged and was revealed to have reunited with Undertaker and looked on as Undertaker assaulted his brother . Undertaker went on to face Kane at Hell in a Cell , but was defeated when Paul Bearer turned on Undertaker and helped Kane retain the World Heavyweight Championship . On the October 15 episode of SmackDown , Undertaker accepted the challenge by Kane for a Buried Alive match at Bragging Rights 2010 for the World Heavyweight Championship , but ended up losing after he was attacked by The Nexus . After the match the gravesite was struck by lightning and his symbol appeared on the grave . It was reported a few weeks before Bragging Rights that The Undertaker was suffering from injured shoulder , when the injury first happened a few months ago and it became apparent that The Undertaker had torn his rotator cuff in the shoulder , WWE planned for the Undertaker to lose a Buried Alive match against Kane at Survivor Series and then rest up his shoulder after the event . When the pain got worse , the call was made to have the Buried Alive match take place at Bragging Rights and get the surgery over with . It has been reported that The Undertaker may not be back in the ring until early 2011 . Defending the Streak ( 2011 – 2014 ) . After the 2011 Royal Rumble , promotional videos showing The Undertaker entering and standing within an old house began airing . Each promo would end with the date 2 – 21 – 11 being burned into the screen . On the February 21 episode of " Raw " The Undertaker returned ; after his lengthy entrance but before he could speak , Triple H returned after an eleven - month absence and confronted The Undertaker . In a unique interaction involving no verbal or physical exchanges , the two stared each other down , performed their signature intimidation actions towards each other before Triple H set his eyes upon the WrestleMania XXVII marquee . The Undertaker responded by turning his attention toward the marquee as well . The Undertaker initially scoffed at Triple H ' s apparent challenge but later accepted . The match was later announced as a No Holds Barred match on WWE ' s website . At WrestleMania XXVII , after surviving three " Pedigrees " and a " Tombstone Piledriver " , Undertaker forced Triple H to tap out to Hell ' s Gate , extending his streak to 19 – 0 . Following the match , The Undertaker was 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 . The two men stared at each other before Undertaker set his attention on the WrestleMania XXVIII marquee . Triple H responded by patting Undertaker on the shoulder before exiting the ring . On February 13 , after Triple H refused the Undertaker ' s challenge for a Wrestlemania rematch , an Undertaker video appeared on the TitanTron . The video featured the Undertaker cutting his own hair with a straight razor before declaring vengeance would be his . 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 be a Hell in a Cell match ; Michaels was later inserted as referee in the match . On April 1 at WrestleMania , The Undertaker defeated Triple H to extend his streak to 20 - 0 . After the match , The Undertaker and Michaels carried Triple H to the entrance stage , where the three embraced . The Undertaker was not seen in any WWE live event thereafter . The Undertaker made an appearance 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 six attacked Undertaker and Kane , but were overpowered by the latter regardless of being outnumbered . Kane and Undertaker delivered two simultaneous " Chokeslam s " , followed by two simultaneous " Tombstone Piledriver s " to Hawkins and Hunico and cleared the ring . At RAW Goes Old School on the March 4 edition of Raw , the Undertaker set on a course to battle him in WrestleMania and eventually he faced CM Punk and won making it 21 - 0 at WrestleMania 29 . After that he goes to Raw and Smackdown to face The Shield with the help of his brother , Kane and Daniel Bryan but gets a taste of their triple powerbomb . 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 a long and " methodical " match , Lesnar defeated Undertaker by pinfall to end the streak . The Undertaker suffered a concussion during the match and was hospitalized afterwards . Return ( 2015 - present ) . In February 2015 , Bray Wyatt began a series of cryptic promos which would lead to Fast Lane , where Wyatt challenged Undertaker to a match at WrestleMania 31 . The Undertaker accepted the challenge on the March 9 episode of Raw , playing mind games of his own . Undertaker would then make his first official appearance since his loss at WrestleMania 30 , sporting longer hair and wearing his WrestleMania 20 attire , defeating Wyatt at WrestleMania 31 to become " 22 - 1 " . At Battleground in July , Undertaker attacked Brock Lesnar during his WWE World Heavyweight Championship match against Seth Rollins , which caused the match to end by disqualification . The next night on Raw , The Undertaker explained his actions as avengement for Lesnar breaking the streak and his constant taunting about it . Later in the evening , after Undertaker and Lesnar brawled throughout the arena and had to be separated . It was announced that they would face off in a WrestleMania XXX rematch at SummerSlam in August . Other media . Calaway appeared in the 1991 film " Suburban Commando " . He also appeared on episodes of " Poltergeist : The Legacy " and " Celebrity Deathmatch " in 1999 . A number of spin - offs have covered The Undertaker ' s character . " Undertaker " comic . In 2005 , Pocket Books released a novel , " Journey into Darkness : An Unauthorized History of Kane " , which dealt largely with Kane but also featured Undertaker as his brother , although they are not related in real life . The Undertaker character was present in the Hindi movie Khiladiyon Ka Khiladi as a villain , played by Brian Lee ( who played the ' fake Undertaker ' in the WWF ) . He was dressed in the western mortician attire adopted by the Undertaker from 1990 to 1993 , and used the Tombstone Piledriver as a finishing move in the film . On November 6 , it was announced that the Undertaker will be in his own feature film that will focus on his origin and more about his powers . It will also star Calaway himself . Personal life . 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 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 . 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 ) . 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 . Boxing and MMA involvement . 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 . 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 ? " He was a close friend of actor Tony Longo and remains close friends with mixed martial artists Pat Miletich , Jeremy Horn , and Matt Hughes . In wrestling . Nicknames