Few superstars have had a career parallel to the Undertaker. The Deadman is one of the few wrestlers to wrestle through the Hulkamania era, all the way to the lockdown era in 2020. He has faced superstars from every single generation. The legend has elevated every superstar who stepped in the ring against him.

Undertaker in the 90s

Undertaker debuted in 1990 at Survivor Series. Managed by Brother Love (Bruce Prichard), Taker wrestled for the Million Dollar Team. He picked up one elimination before getting counted out with Dusty Rhodes. The following year at WrestleMania, Undertaker picked up his first win at the PPV. Jimmy Snuka was the first victim of the Streak.

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Taker won his first WWE Championship in 1991. He faced Hulk Hogan at Survivor Series and Tombstoned him atop a steel chair to win his first title. He would hold it for just a few days before losing it back to Hogan at Tuesday in Texas. Taker would continue winning at WrestleMania. He racked up wins against Giant Gonzalez, King Kong Bundy, and Diesel.

Taker would main event his first WrestleMania in 1997. Facing Sid Vicious, Taker would beat the man for the WWE Championship. That was only his second title win in WWE. 1997 would be a defining year for the Undertaker. The debut of his kayfabe brother Kane, and his rivalry with Shawn Michaels highlighted his incredible year.

The American Badass and Big Evil era

In the year 2000, at the peak of the Attitude Era, Undertaker debuted his new persona. They termed it the American Badass, who rode a bike to the ring and infused MMA into his repertoire. He won the Undisputed Championship, the Hardcore Championship, and the Tag Team Championships alongside Kane. During this run, the Brothers of Destruction were formed.

Taker’s brutal rivalry with Brock Lesnar defined this era. The newly crowned WWE Champions needed a legitimate threat to his throne, and Taker fit the bill perfectly. They clashed in a violent and bloody Hell in a Cell match, and a strange biker chain match. The era of the American Badass ended with Kane turning on his brother. He helped bury him alive and claimed that he was, “dead and buried forever”.

Return of the Deadman

Undertaker returned as the Deadman at WrestleMania XX. After demolishing Kane, the Deadman pursued championship gold, and looked to reclaim his spot atop the WWE. In 2006, Taker had a blistering rivalry with Kurt Angle over the World Heavyweight Championship. Their match at No Way Out is one of the finest matches in WWE history.

Taker won the 2007 Royal Rumble match and beat Batista for the World Heavyweight Title at WrestleMania 23. This kick-started a year-long rivalry between the two behemoths. Their Hell in a Cell match at Survivor Series served as a fitting climax, as Taker moved on from one feud to the other.

Edge attacked Undertaker inside Hell in a Cell and cost him the World Championship. Taker and Edge would finally meet at WrestleMania 24, where the Deadman would submit The Rated-R Superstar with the Hell’s Gate. The two would trade the championship back and forth, before facing off inside Hell in a Cell at SummerSlam 2008. Taker won that match and proceeded to choke slam Edge from the top of a ladder through the ring.

WrestleMania classics against Shawn Michaels and Triple H

From 2009 to 2012, fans mostly remembered Undertaker for his brilliant matches at WrestleMania against Shawn Michaels and Triple H. Michaels and Taker wrestled at WrestleMania 25, in probably the greatest WrestleMania match of all time. The duo would face off the following year with HBK’s career on the line.

Taker drove Michaels’ career into the proverbial burial plot, before moving on to Triple H. The Game and the Deadman would have two instant classics at WrestleMania 27 and 28. Their Hell in a Cell match was a brilliant showcase of emotional storytelling. It contained violence, and a mutual show of respect between Shawn, HHH, and Taker.

The End of the Streak

Taker’s streak ended at the hands of Brock Lesnar in 2014. Their WrestleMania 30 clash would cause Undertaker’s record changing to 21-1. Lesnar and Taker feuded in 2015, with their rivalry effectively ending inside Hell in a Cell. Taker would also celebrate his 25th Anniversary in WWE at Survivor Series 2015, with a win over the Wyatt Family.

Undertaker would continue to wrestle at WrestleManias. He faced some of the biggest names in the modern crop of WWE. Roman Reigns became the second man to beat Taker at The Showcase of the Immortals. Taker returned the following year to bury John Cena in less than five minutes. He wrestled his last match at WrestleMania 36 opposite AJ Styles.

Undertaker announced his retirement

The Deadman announced his retirement from WWE at Survivor Series 2020. As he celebrated his 30th anniversary, he thought it would be the perfect place to announce the disheartening news to millions of his fans around the world. It was a suitable ending to a near-perfect WWE career.