The Undertaker has two contrasting gimmicks: "The Deadman", an undead, occult-like figure, and "The American Bad Ass", a biker. The specialty matches connected to The Undertaker are the Casket match, the Buried Alive match, the notorious Hell in a Cell, and the Last Ride match. The Undertaker's kayfabe half-brother is Kane, with whom he has teamed as the Brothers of Destruction. The Undertaker is undefeated at WrestleMania with a 19–0 record. Among other accolades, he is a eight-time World Champion: a four-time WWF/E Champion and three-time World Heavyweight Champion as The Undertaker, and a one-time USWA Unified World Heavyweight Champion as Master of Pain. The Undertaker is also a one-time WWF Hardcore champion, and 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 at number thirty and win. He has been named by WWE as the greatest big man of all time,the scariest superstar of all time and also the best pure striker in the history of the game. Calaway is also the only active wrestler who appeared on the company's very first Raw program, who remains with WWE today.
Calaway made his debut in 1984 in World Class Championship Wrestling 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 and joined the Continental Wrestling Association (which became the United States Wrestling Association after Jerry Jarrett merged CWA with WCCW), wrestling 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 Punisher", Calaway won the WCWA Texas Heavyweight Championship on October 5, 1989 when Eric Embry forfeited the title.
Calaway made his WWF debut as "Cain The Undertaker" at a taping of WWF Superstars on November 19, 1990.It should be noted, however, that the concept of The Undertaker character was not presented to Calaway until after he signed with Vince McMahon. He stated in a 2003 interview with WWE Magazine that he was terrified that he would be hatched from an oversized egg at the 1990 Survivor Series, which had been on display at WWF events for months and heavily hyped on television, and appear as an "egg man" character.The appearance of The Undertaker's first Deadman persona was modeled after a mortician from old Western movies, wearing a trench coat and black hat with grey gloves and boot covers. Under this Deadman persona, he was impervious to pain, something accomplished by Calaway no-selling his opponents' attacks. Calaway made his official on-camera debut on November 22 at Survivor Series as a heel when he was the mystery partner of Ted DiBiase's Million Dollar team, where he was simply called The Undertaker.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. Shortly after Survivor Series, "Cain" was dropped from his name, and he was called simply The Undertaker. It was at this time that The Undertaker switched managers from Brother Love to Paul Bearer — a histrionic, ghostly character, almost always seen bearing an urn from which The Undertaker was said to draw mystical power, reviving his strength during his matches. During his heel run, Undertaker would place his defeated opponents (almost always jobbers) in a bodybag and carry them to the back.
After WrestleMania X, Ted DiBiase introduced an Undertaker back to the WWF. This Undertaker, however, played by Brian Lee, was an impostor Undertaker (dubbed the "Underfaker" by fans) and led to the return of the real Undertaker at SummerSlam, appearing as a new version of his original Deadman persona, replacing grey with purple. The Undertaker defeated the impostor after three Tombstone Piledrivers.At Survivor Series, The Undertaker defeated Yokozuna in a rematch, another casket match. 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 stole The Undertaker's urn, and antagonized him by melting it into a large gold necklace and attacking the Undertaker.Later, The Undertaker defeated Kama in a casket match at SummerSlam.Several weeks later, The Undertaker injured his orbital bone near his eye, forcing a period of absence for surgery, until his return at Survivor Series.
After the Royal Rumble 2011, promos 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 following the Elimination Chamber 2011, The Undertaker returned to Raw, but was interrupted by Triple H, who also returned moments later and confronted The Undertaker. The two of them stared at the WrestleMania XXVII marquee, which turned out to be a challenge that The Undertaker accepted. The match was then made official on WWE's official website and then turned into a No Holds Barred match. 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 taken out on a stretcher.
Calaway graduated from Waltrip High School in 1983 where he was a member of the basketball team.Calaway married his first wife, Jodi Lynn, in 1989, and they had a son, Gunner, born in 1993, before the marriage ended in 1999.Calaway married his second wife, Sara, in St Petersburg, Florida on July 21, 2000. The couple had two daughters together: Chasey (born on November 21, 2002) and Gracie (born on May 15, 2005). As of 2007, he and Sara were divorced, and he was romantically linked to former wrestler Michelle McCool, whom he married on June 26, 2010, in Houston, Texas.