Shawn Michaels

The Undertaker and Shawn Michaels were must-see rivals during the WWF’s Attitude Era. Their most memorable matches during this time were at 1997’s Badd Blood: In Your House in the first-ever Hell In A Cell match, and their Casket Match at the 1998 Royal Rumble.

Their in-ring chemistry would stand the test of time. Almost ten years later, they would have classic matches at Wrestlemania 25 in 2009 and Wrestlemania 26 in 2010. Their 2010 encounter was a Streak vs. Career match where if The Undertaker lost, it would be his first ever Wrestlemania loss. But if Michaels lost, he would have to retire from in-ring competition. We won’t spoil the outcome, but let’s just say it was a match to remember.

Mankind

Mick Foley‘s willingness to put his body on the line elevated the level of danger in his matches with The Undertaker. His portrayal of the deranged Mankind made their rivalry both fun and uncomfortable to watch.

Taker and Mankind’s violent feud would span a series of matches. They took part in the inaugural Boiler Room Brawl at SummerSlam 1996, but their most memorable encounter took place at the 1998 King Of The Ring in a Hell In A Cell match, where Taker tossed Mick Foley from the top of the 20-foot cage, sending him crashing into an announcer’s table at ringside.

Kane

Glenn Jacobs played a plethora of characters before finding success in the WWF as The Undertaker’s “brother” Kane. In 1997, Undertaker’s manager, Paul Bearer, turned against him, revealing his brother—who he believed died in a fire during childhood—was alive and coming for revenge. Kane’s arrival took place on the same night as Taker and Michael’s Hell In A Cell Match at Badd Blood.

Their feud gave birth to WWF’s first Inferno Match, a match where the entire ring is surrounded by fire and the only way to win is to set your opponent on fire. When they weren’t trying to murder each other, Kane and his older brother would join forces. Dubbed The Brothers of Destruction, they would wreak havoc on the WWF/E’s tag team division.

Stone Cold Steve Austin

WWF’s Attitude Era also saw the rise of the most popular wrestler in wrestling history in Stone Cold Steve Austin. Austin’s edgy character was more in line with the WWF’s core demographic at the time. He would break in the mold of the traditional “good guy” in pro wrestling, a trope created by characters like Hulk Hogan.

While Austin was becoming the company’s top good guy, The Undertaker was in the middle of his run as the resident evildoer and head of the faction called The Ministry of Darkness. Their collision course consisted of Undertaker sacrificing Austin, trying to inject him with embalming fluid, and a First Blood match at 1999’s Fully Loaded pay-per-view.

Triple H

The Undertaker and Triple H had matches at the height of their popularity, but their best matches came towards the end of their runs as full-time wrestlers. Much like his best friend Shawn Michaels, Triple H had back to back classics with The Deadman at Wrestlemania 27 and 28. The match at 28 was known as the “End of An Era” match. Shawn Michaels was the special guest referee, with the match stipulation being one Michaels and Taker made famous…Hell In A Cell.

Brock Lesnar

Much like The Undertaker, Brock Lesnar‘s presence and resume made him as feared as he is respected. He was WWE’s fastest rising star before leaving the company back in 2004 due to his dislike of the rigorous travel schedule.

Upon his return in 2012, Lesnar would dominate the same way he did when he first debuted back in 2002. His path of destruction would lead to Wrestlemania 30 in 2014, where Brock would be the 22nd opponent to face Undertaker at the premiere event. Many had Taker pegged as the winner because this was an event he dominated for 20 years.

But on this night, the world came to a standstill. Brock would accomplish the impossible and beat The Undertaker.

The shocking victory made Undertaker’s record 21-1 at the Showcase of the Immortals.