Widely regarded as one of the greatest professional wrestlers of all time, Calaway is best known for his on-screen career in WWF/E from 1990 to 2020, in which he performed his critically acclaimed Undertaker gimmick.
Although retired from professional wrestling, Calaway remains employed for WWE through a 15-year contract signed in 2019.
Calaway began his career in 1987, working under various gimmicks for World Class Championship Wrestling (WCCW) and other affiliate promotions.
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 into a horror-themed gimmick with the name, “The Undertaker”, once joining the WWF.
Portraying an undead, funereal, macabre character, he gained significant mainstream popularity and won the Wrestling Observer Newsletter awards for Best Gimmick a record-setting 5 years in a row.
A textbook example of WWE’s Golden Age of freakish gimmicks.
Undertaker was intent on disrupting the confidence of his rivals while feuding with and combating them, done through varied alarmist tactics: delivering caskets, corpse-like effigies, theatrically chilling entrances, funeral tolling, etc.
The longest-tenured wrestler in company history at 30 years, The Undertaker is one of the most prominent figures of the Attitude Era–a high rating, envelope-pushing generation of the WWF/E in the latter 1990s.
Desiring to perform under a gimmick truer to himself, Calaway expanded on The Undertaker gimmick by assuming a biker identity, dubbed “American Badass”, in 2000.
Calaway resurrected The Undertaker’s Deadman identity in 2004 with residual elements of his biker identity blended.
For the better part of his career, The Undertaker was observed as a focal point of WWE’s flagship annual event, WrestleMania, where he became esteemed for The Streak—a series of 21 straight victories.
He is also known for pairing with his in-storyline half-brother Kane, with whom he had alternatively feuded and teamed off and on with as The Brothers of Destruction from 1997 through 2020.
During his active career under The Undertaker gimmick, Calaway won the WWF/E Championship four times, the World Heavyweight Championship three times, the Hardcore Championship once and the World Tag Team Championship six times.
He also won the Royal Rumble match in 2007.
He is one of WWE’s most prolific pay-per-view performers, headlining several pay-per-view events, including WrestleMania on five occasions.
The Undertaker retired from professional wrestling in 2020 and made a farewell appearance at that year’s Survivor Series event, 30 years to the day after he made his on-screen debut for the company at the same pay-per-view brand.
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.
Calaway learned “on the job” thereafter.
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 emulate Jardine’s top rope walk.
PWInsider‘s Mike Johnson stated, “Undertaker using some of Jardine’s style eventually morphed into this story that he was trained by Jardine.”
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.
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.
In the 1991 King of the Ring, 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 the manager/wife Miss Elizabeth with a steel chair when Undertaker stopped him, turning face 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.
He then feuded extensively with wrestlers managed by Harvey Wippleman throughout 1992 and 1993, such as Kamala and Giant González.
Also at this time, he headlined the first episode of Monday Night Raw on January 11, 1993, with a victory over Damien Demento.
According to Calaway, working with González “…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 WrestleMania after the use of chloroform.
His rivalry with Yokozuna culminated in a WWF Championship casket match for the WWF Championship at the Royal Rumble in January 1994.
During the match, 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.