The Undertaker is widely regarded as one of the greatest professional wrestlers of all time, Calaway spent the vast majority of his career wrestling for WWF/E, and is best known for his critically acclaimed "Deadman" Undertaker gimmick, for which he was inducted into the WWE Hall of Fame in 2022. Calaway remains employed for WWE through a 15-year contract signed in 2019.
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, turned WWE) in 1990.
Calaway was rebranded as "The Undertaker" once joining the WWF. As one of WWE's most popular and enduring characters, The Undertaker is famed for his undead, funereal, macabre "Deadman" persona, which gained significant mainstream popularity and won him the Wrestling Observer Newsletter award for Best Gimmick a record-setting 5 years in a row. 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 ratings, envelope-pushing generation of the WWF/E in the latter 1990s. Calaway expanded on The Undertaker gimmick by assuming a biker identity, dubbed "American Badass", in 2000. Calaway later resurrected Deadman Undertaker in 2004, with residual elements of American Badass Undertaker remaining.
The Undertaker retired from professional wrestling in 2020 and made a farewell appearance at that year's Survivor Series, 30 years to the day from his on-screen debut for the company at the same pay-per-view event brand. The Undertaker was later inducted into the WWE Hall of Fame as the headline inductee for the Class of 2022.