The Undertaker once again reinvented his character in the Attitude Era. During this period which is from 1997-2002, The Undertaker went from his "Lord of Darkness" persona to the "American Badass." The Phenom would turn heel twice in 1998 and 2001 respectively. From late 1998 to early 1999, Undertaker would rule his Ministry of Darkness stable.
Some of the matches from the Attitude Era have been The Undertaker's greatest in his entire career. During this time, he faced off against some of his greatest rivals, putting on highly memorable and entertaining performances. Let's look back at The Deadman's greatest contributions during the time WWE oozed attitude!
10 Undertaker & Stone Cold Steve Austin Vs Mankind & Kane, Fully Loaded: In Your House
Before The Undertaker and Stone Cold Steve Austin could turn their attention to their highly anticipated WWF Championship match at SummerSlam 1998. The pair had a mini roadblock on the "Highway to Hell." The pair teamed up to face World Wrestling Federation Tag Team Champions Mankind and Kane in the main event at Fully Loaded: In Your House in July 1998.
The four superstars were all feuding with each other throughout 1998, which made this tag team match interesting. While it is not a tag team classic, it featured four legends. The Undertaker turned up to the arena late, but Taker and Austin could work as a cohesive unit enough to win the match.
Austin tagged The Undertaker in, who chokeslammed both Mankind and Kane, followed by a Tombstone Piledriver on his brother Kane, winning the WWF Tag Team Championships in the process. However, Taker would walk out of Fully Loaded with both belts on his shoulder.
9 Undertaker Vs Triple H, WrestleMania X-Seven
Another underrated classic between two of the great superstars of all time, The Undertaker and Triple H went one-on-one at WrestleMania 17 on April 1, 2007. Triple H had Motorhead play him down the aisle for the first time at the Reliant Astrodome. Taker would come down on his motorcycle to the delight of his hometown fans in Houston.
Taker's face was a crimson mask as Triple H nailed him with a sledgehammer. The American Badass would get the last laugh with The Last Ride. It was this WrestleMania that the streak would be acknowledged for the first time as Jim Ross said Taker was 9-0 on commentary.
8 Undertaker Vs Rob Van Dam, Vengeance 2001
In the latter stages of 2001, The Undertaker turned heel for the third time in his career. The Phenom was looking for respect for his decade of dominance. Taker's long hair was cut short, and Jim Ross tried to give Undertaker a new nickname, "Booger Red." Thankfully, Booger Red did not stick with The Undertaker for long.
At Vengeance 2001, Taker would challenge Rob Vand Dam for the WWF Hardcore Championship. Taker deserves a lot of credit for this match as he was out of his comfort zone. He showed he was Hardcore as he chokeslammed Van Dam off the stage through some tables. Taker victoriously rode out of San Diego with the Hardcore Championship in tow. A scary prospect as Hardcore Champion, Jerry Lawler would say on commentary, "That's what's scary, The Undertaker is the Hardcore Champion."
7 Undertaker Vs Stone Cold Steve Austin, Rock Bottom: In Your House
Throughout the latter stages of 1998, The Undertaker and Stone Cold Steve Austin would take part in one of the greatest rivals in WWE history. Their final clash of the year was taken to the next level. At Rock Bottom: In Your House on December 13, 1998, Austin and Taker would face off in the second-ever Buried Alive match.
Austin had to defeat Taker to qualify for the 1999 Royal Rumble match. This match is often overlooked in their rivalry, but it was brutal as they used the gravesite to fight each other. Kane would interfere and Tombstone his brother, helping Austin gain the victory. The helpless Deadman was buried alive.
6 Undertaker Vs Bret Hart, SummerSlam 1997
The Undertaker was in the midst of his best-ever WWF Championship run in 1997. At SummerSlam, he defended the title against Bret Hart, who was now a heel. Shawn Michaels was the Special Guest Referee in this encounter.
This match would shape up things to come in the latter part of the year. Taker's five-month title reign came to a halt as Michaels accidentally hit him with a steel chair. Hart would pin Taker to win his fifth and final WWF Championship.
5 Undertaker Vs Kurt Angle Vs Stone Cold Steve Austin Vs Rikishi Vs The Rock Vs Triple H, Armageddon 2000
At Armageddon 2000, The Undertaker would debut Limp Bizkit's Rollin' as his new theme song. Taker would compete in the only six-man Hell in a Cell Match for the WWF Championship. Kurt Angle was the champion, who Taker was close to beating the prior month at Survivor Series.
This Hell in a Cell match is one of the greatest in history. Barring Rikishi, it featured five WWE Champions, including The Rock, Stone Cold, and Triple H. Taker was unsuccessful once more, but the most memorable moment of this match is Taker making Rikishi famous by chokeslamming him off the Hell in a Cell into the back of Mr.McMahon's truck, which was parked at ringside.
4 Undertaker Vs Kane, WrestleMania XIV
The rivalry between The Undertaker and Kane isn't just one of the greatest rivalries in the Attitude Era, it is one of the greatest rivalries, period. The storytelling was done masterfully by Paul Bearer, who would talk about Kane for months in 1997. Kane finally made his debut at Badd Blood: In Your House, costing The Undertaker a shot at the WWF Championship.
The brothers would finally lock horns at WrestleMania 14. It is by far the best match in their rivalry. Kane would become the first man to kick out of The Undertaker's Tombstone twice. Taker would finally pick up the victory with a third Tombstone, but Kane and Bearer would assault The Phenom after the match.
3 Undertaker Vs Stone Cold Steve Austin, SummerSlam 1998
The Highway to Hell finally arrived at SummerSlam 1998 when Taker and Austin clashed for the WWF Championship. The Phenom was searching for his third WWF Championship and despite being a face, he was portraying a devilish side that would come into full effect a couple of months later.
The two brawled back-and-forth in this match. The two former WWF Tag Team Champions put on a great show inside Madison Square Garden. Undertaker put Austin through the announce table with a leg drop off the top rope. However, Austin would recover and give a Stone Cold Stunner to The Deadman in one of the best WWF Championship main events in SummerSlam history.
2 Undertaker Vs Shawn Michaels, Badd Blood: In Your House
The main event of Badd Blood: In Your House featured the first-ever Hell in a Cell match. The Undertaker squared off with WWF European Champion Shawn Michaels. The winner would go on to face Bret Hart for the WWF Championship at Survivor Series 1997.
This was a brutal match with Taker and Michaels climbing to the top of the cell. Halfway through the match, Michaels would fall off at the side of the cell. The Deadman was closing in on the victory but Kane made his debut, delivering a Tombstone to his brother, allowing Michaels to pick up the win.
1 Undertaker Vs Mankind, King Of The Ring 1998
Mankind would be a thorn in The Undertaker's side since the night after WrestleMania XII. Mankind debuted on the April 1, 1996 edition of Raw, assaulting Taker. Both men had memorable battles, including a Broiler Room Brawl at the 1996 SummerSlam. But in 1998, the stakes were higher as the pair would reignite their rivalry in a Hell in a Cell match at the King of the Ring.
In one of the scariest moments in WWE history, The Undertaker threw Mankind off the top of the cell onto the commentary table. Mankind was not done there as he climbed back up again, but Taker chokeslammed him through the ring. It was a pivotal moment in the Attitude Era, a night where Mankind earned respect from his peers and a lot of fans.
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