As part of the 2001 Invasion angle, the Undertaker's next nemesis was Diamond Dallas Page. Page was obsessively following the Undertaker's wife Sara. At SummerSlam 2001, 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. They were the first team to hold both the WCW and WWF tag team titles simultaneously.
At Survivor Series 2001, Undertaker teamed up with Kane, the Rock, Chris Jericho, and The Big Show to take on The Alliance's Steve Austin, Booker T, Rob Van Dam, Shane McMahon, and Kurt Angle. 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 famous long hair short and now called himself Big Evil. At Vengeance 2001, the Undertaker beat Van Dam to capture the WWF Hardcore Championship.
2002-2003
At the 2002 Royal Rumble, Maven eliminated the Undertaker 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 #1 contendership for the WWF Undisputed Championship. Their feud continued, with the Rock costing the Undertaker his match with Maven for the Hardcore Championship. The two faced off at No Way Out 2002, but the Undertaker lost due to interference from Ric Flair. Flair declined a challenge to wrestle Undertaker at WrestleMania X8, and, as a result, Undertaker assaulted his son David Flair. Ric Flair eventually accepted the match after the Undertaker threatened to inflict the same punishment on Flair's daughter. A no disqualification stipulation added, the Undertaker emerged with the win, improving his WrestleMania record to 10-0.
Undertaker defeated Steve Austin at Backlash 2002 to win the #1 contendership for the WWF Undisputed Championship. Later that night, he helped Hulk Hogan win his title match against Undisputed Champion Triple H. The Undertaker went on to defeat Hogan for his fourth world championship at Judgment Day 2002.
Undertaker soon turned face after he faced Jeff Hardy in a Ladder Match, raising Hardy's hand after the match as a sign of respect. However, Undertaker lost his title at Vengeance 2002 to the Rock in a Triple Threat Match that also involved Kurt Angle, although he wasn't even pinned. When contracts were open during the end of the feud between McMahon and Flair, the Undertaker switched from RAW to SmackDown!, alongside former RAW talent Brock Lesnar, Chris Benoit, and Eddie Guerrero. After defeating Test at SummerSlam 2002, Undertaker challenged Brock Lesnar in a title match at Unforgiven 2002, but the match ended in a double-DQ. Their feud carried over to No Mercy 2002 in a Hell in a Cell Match. Undertaker worked the match with a broken hand and eventually lost to the champion. Undertaker then suffered a kayfabe injury after the Big Show threw him off the stage in Memphis, sparking a feud.
The Undertaker returned at the 2003 Royal Rumble drawing #30, but he was the last man eliminated by Brock Lesnar. He then continued his feud with Big Show. After Nathan Jones came to the Undertaker's aid at No Way Out 2003, Undertaker began to train Jones to wrestle, and the two were scheduled to fight Big Show and A-Train in a tag team match at WrestleMania XIX. However, Jones was removed prior to the match, making it a handicap match, which Undertaker won with the help of Jones, improving his WrestleMania record to 11-0.
Undertaker went on to feud against the Full Blooded Italians, John Cena, A-Train, Brock Lesnar, and Big Show. He had two WWE Championship opportunities over the course of the year. The first, on the September 4, 2003 SmackDown!, against Kurt Angle, ended in a no contest. The second, at No Mercy 2003, was a Biker Chain Match between Undertaker and Lesnar. With the help of Vince McMahon, Lesnar won, making it his second straight successful No Mercy WWE Title match against Undertaker.
At Survivor Series 2003, Undertaker lost his Buried Alive Match against Vince McMahon when Kane interfered. After the Undertaker disappeared for some time following the match, Kane claimed that he was dead and buried forever.
2004-2005
In the weeks 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 finally returned, using the Deadman persona, again accompanied by Paul Bearer, and he defeated Kane. This persona could be best described as a hybrid of the classic Undertaker and the American Bad Ass. Three months later, Paul Bearer was kidnapped by the Dudley Boyz at the direction of Paul Heyman, who then took "control" of Undertaker in the storyline. At The Great American Bash 2004, Undertaker was forced to fight a handicap match against the Dudleys; and if he lost, Paul Heyman would bury Paul 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 Bearer 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 would also remain as a face.
After defeating the Dudley Boyz, Undertaker challenged WWE Champion John Bradshaw Layfield to a title match at SummerSlam 2004, where Undertaker lost when he disqualified himself. At No Mercy 2004, Undertaker and JBL competed in the first ever "Last Ride" match, although Undertaker lost after Heidenreich interfered. After taking care of Heidenreich, Undertaker turned his focus to the WWE Championship once again. Along with Eddie Guerrero and Booker T, he challenged Bradshaw to a championship rematch at Armageddon 2004. The match turned into 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 2005 Royal Rumble, where Undertaker sealed Heidenreich in a casket for the victory.
Soon afterward, Randy Orton challenged the Undertaker to a match at WrestleMania 21, claiming that he would be the one to 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 John Bradshaw Layfield, thanks to interference from Randy Orton. General Manager Theodore Long booked Muhammad Hassan in a match against the Undertaker at The Great American Bash 2005, where the Undertaker defeated Hassan in Hassan's last match in WWE. As a result of the win, he became #1 contender to the World Heavyweight Championship. However, JBL felt that he should be #1 contender. On the following SmackDown!, Undertaker lost a #1 contender match against JBL, once again due to interference from Randy Orton. With this, Undertaker resumed his feud with Orton.
At SummerSlam 2005, Undertaker and Randy Orton had a WrestleMania rematch, which Orton won. After weeks of their feud building up, Undertaker defeated Randy on the second episode of Friday Night SmackDown! The two taunted each other with caskets, leading to a casket match, in which Undertaker lost to Randy and his father "Cowboy" Bob Orton, at No Mercy 2005. After the match, the Ortons poured gasoline on the casket and set it afire, much like Kane did in 1998. However, when the charred casket was opened, the Undertaker had once again vanished. He then made a dramatic return at the 2005 Survivor Series, emerging from a burning casket.
Despite a controversial attack involving the late Eddie Guerrero's lowrider on the November 29, 2005 SmackDown! special, Undertaker returned on the Friday SmackDown! show to haunt Orton and set up a Hell in a Cell match at Armageddon 2005. After winning the Hell in a Cell match, Calaway took a short hiatus from wrestling.
2006-2007
At the 2006 Royal Rumble, Undertaker returned during Kurt Angle's celebration of his world title defense. He entered on a horse drawn cart and made his intentions known by destroying the ring with lightning bolts. Undertaker lost his match with Kurt Angle at No Way Out 2006 after a gruelling thirty minute bout. Undertaker cornered Angle after the match, and after a stare down, told Angle that he had his number and that he wasn't finished with him yet.
The Undertaker had his No Way Out rematch for the World Heavyweight Championship against Angle on SmackDown!. Mark Henry attacked Undertaker from behind, costing him the title. Undertaker challenged Mark Henry to a Casket Match at WrestleMania 22, and Henry, like Orton a year before him, vowed to end the Undertaker's WrestleMania winning streak. Undertaker defeated Mark Henry to become 14-0 at WrestleMania, keeping his undefeated streak alive. During a rematch on the April 7 edition of SmackDown!, The Great Khali made his debut and began an assault on the Undertaker.
The Undertaker was not heard from until the May 5 edition of SmackDown!, as General Manager Theodore Long delivered a challenge from Undertaker to Khali for a match at Judgment Day 2006. Undertaker would go on to lose the match to Khali and 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 was removed from the match, due to elevated liver enzymes, and 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 the Undertaker shortly before the match. Khali was then challenged to a Last Man Standing match at SummerSlam 2006 after interfering in Undertaker's match with World Heavyweight Champion King Booker. After Khali refused the challenge for SummerSlam, Teddy 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. After his victory, Undertaker was not seen for several weeks.
The Undertaker returned to face United States Champion Mr. Kennedy at No Mercy 2006 but was disqualified after he hit Kennedy with the championship belt. On the November 3 edition of Smackdown!, the 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 MVP, with whom Kane was feuding at the time. Undertaker lost against Mr. Kennedy in a First Blood match at Survivor Series, due to interference from MVP, but finally defeated Kennedy in a Last Ride match at Armageddon 2006. The two continued into 2007 as Kennedy cost Undertaker two World Heavyweight Championship opportunities for a championship match at the 2007 Royal Rumble.
At the Rumble, in his eighth attempt, Undertaker won his first Royal Rumble match, last eliminating Shawn Michaels, and becoming the first man to enter the Rumble at No. 30 and go on to win the match.[5] He then challenged and defeated Batista at WrestleMania 23 to win his first World Heavyweight Championship, ten years after he defeated Sycho Sid for the WWE Championship at WrestleMania 13. By defeating Batista, Undertaker's undefeated streak at Wrestlemania advanced to 15-0.
Finishing and Signature moves
Tombstone Piledriver (Kneeling belly to belly piledriver)
Last Ride (Elevated powerbomb)
Chokeslam
Double chokeslam (with various tag team partners whether simultaneous or to one person)
Old School (Arm twist ropewalk chop)
Takin' Care of Business (Dragon sleeper)
Big boot / Running big boot
Sidewalk slam
Snake eyes followed by a running big boot
Running DDT
Guillotine leg drop onto the apron-bound opponent
Running leg drop
Reverse STO
Plancha over the top rope
Triangle choke
Corner clothesline
Flying clothesline