The Undertaker had two contrasting personas throughout his career. The first was “The Deadman,” an undead, occult-like figure that went through various iterations. It began with a Western mortician character in November 1990 and evolved into the Satanic Ministry of Darkness leader in September 1999. He returned as a hybrid of all his previous incarnations in March 2004. 

The second persona was “The American Bad Ass,” a biker character he portrayed from May 2000 to November 2003. The Undertaker’s gimmicks were associated with specialty matches such as the Casket, Buried Alive, Hell in a Cell and Last Ride matches. Another important aspect of his character was his half-brother Kane, with whom he had feuds and alliances as the Brothers of Destruction.

The Rise

Calaway’s early career began 1984 in World Class Championship Wrestling (WCCW) under the ring name “Texas Red.” He later wrestled in various promotions such as CWA, WCW, and New Japan Pro Wrestling before signing with the WWF in October 1990.

He debuted as “Cain the Undertaker” but soon dropped the “Cain” from his name. Undertaker’s WrestleMania debut came at WrestleMania VII, where he defeated “Superfly” Jimmy Snuka. He had notable feuds with wrestlers such as Ultimate Warrior, Randy Savage, and Hulk Hogan. Undertaker won his first WWF Championship at Survivor Series but dropped it back to Hogan at This Tuesday in Texas six days later.

The Undertaker feuded with Jake “The Snake” Roberts, Kamala, and Giant Gonzales in the following years. He took a hiatus after a casket match loss against Yokozuna at the Royal Rumble, during which his “spirit” appeared from inside the casket, hinting at his return.

After his return, The Undertaker faced an “Underfaker” clone played by Brian Lee, leading to a showdown between the two at SummerSlam, which the real Undertaker won. He had another casket match against Yokozuna at Survivor Series, where he won with the help of Chuck Norris as a special guest enforcer.

The Streak

The Undertaker was best known for his undefeated streak at WrestleMania, which stood at 21-0 until he lost to Brock Lesnar at WrestleMania 30. Throughout his career, he held numerous championships, including the WWF/E Championship four times, the World Heavyweight Championship three times, and the USWA Unified World Heavyweight Championship once under the character “The Master of Pain.” He also won seven World Tag Team championships: six WWF Tag Team Championships and one WCW Tag Team Championship. Additionally, he won the 2007 Royal Rumble and became the first wrestler to enter the event last and best.

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