The Undertaker is one of the all-time greats, and he featured heavily in the New Generation Era with a variety of outstanding feuds, and others failed to live up to the hype.
The Undertaker made his legendary debut at Survivor Series 1990 and on his first anniversary in WWE, The Deadman defeated Hulk Hogan for his first WWE Championship at the age of 26. Soon, Undertaker turned babyface and he was a face for the entirety of the New Generation Era spanning from 1993-1997. Undertaker was one of the major stars in the New Generation Era with the likes of Hulk Hogan and Randy Savage no longer a part of the fold by plying their trade in WCW.
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Undertaker was jostling for the top position in the New Generation Era with the likes of Bret Hart, Shawn Michaels, Diesel, and Steve Austin to an extent. Undertaker was a key component in this era, and some of the storylines he was involved in were off the charts, but others were underwhelming.
15 Rivalry With Giant Gonzalez
The Undertaker's rivalry with Giant Gonzalez began when Gonzalez made his WWE debut at the 1993 Royal Rumble and he towered over Undertaker. He wasn't an official entrant in the Royal Rumble match, but he caused some damage.
Gonzalez eliminated Undertaker which led to an underwhelming match at WrestleMania 9 which Undertaker won by disqualification. Nevertheless, their seven-month feud was curtailed at SummerSlam 1993 when Undertaker saw off Gonzalez in a Rest in Peace match.
14 Seeing Double
The Undertaker was on the shelf for seven months after the 1994 Royal Rumble to heal some injuries, and in his absence, Ted DiBiase introduced an impostor Undertaker. This led to Undertaker returning at SummerSlam 1994 to square off with his doppelganger.
Undertaker reinvented himself for the first time in his WWE career as he traded his trademark gray for purple. They main evented SummerSlam, but Undertaker's grand entrance alongside Paul Bearer was more memorable than the match itself. Leslie Nielsen featured in the case with Undertaker prevailing, and as Nielsen stated "the case is closed."
13 Preventing Faarooq From Making History
The main event of King of the Ring 1997 featured The Undertaker defending the WWE Championship against Faarooq. Faarooq was the first black man to win the WCW World Heavyweight Championship, and he was aiming to become the first black man to capture the WWE Championship.
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Their rivalry was short-lived, and Paul Bearer briefly managed Undertaker once again as he threatened to unveil a dark secret. As expected, Undertaker retained the WWE Championship in a forgettable feud.
12 The Beginning Of A Second WWE Championship Reign
Shawn Michaels losing his smile caused the WWE Championship title picture heading into WrestleMania 13 to be chaotic. The Undertaker found himself challenging Sycho Sid for the WWE Championship in the main event of WrestleMania 13.
It was the first time that the Phenom headlined WrestleMania, and unfortunately, the match was diabolical. Nonetheless, Undertaker had his WrestleMania moment as he dethroned Sycho Sid to kickstart his second WWE Championship run.
11 The Deadman Faces The Bizarre One
The Intercontinental Championship was one of the championships that eluded The Undertaker from his illustrious career. He began feuding with Goldust, and they clashed over the Intercontinental Championship in a casket match at In Your House 8: Beware of Dog.
Undertaker was closing in on the title, but Mankind emerged from the casket and incapacitated Undertaker with the Mandible Claw. A couple of months later, Undertaker and Goldust clashed again with Goldust no longer the Intercontinental Champion, Undertaker picked up a win by disqualification.
10 Clashing With King Mabel
The Undertaker suffered a shocking quarterfinal loss to Mabel in the 1995 King of the Ring tournament and he went on to be crowned as the winner of the tournament and was rechristened as King Mabel. However, Mabel legitimately broke Undertaker's orbital bone.
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Undertaker was out of action for a couple of months but he returned to in-ring competition at Survivor Series 1995 with a Phantom of the Opera-like mask. Undertaker struck fear in King Mabel's heart and Undertaker got the last laugh when he beat Mabel in a casket match.
9 The Million Dollar Corporation Fail To Conquer The Undertaker
The majority of The Undertaker's 1995 was feuding with Ted DiBiase's Million Dollar Corporation. At the Royal Rumble, Undertaker saw off IRS in an average match. Undertaker's match with King Kong Bundy at WrestleMania 11 was in the works at the Rumble as they had a standoff with IRS stealing the urn.
Undertaker saw off Bundy in his fourth WrestleMania appearance, and his rivalry with the Corporation finally halted at SummerSlam. The Undertaker was pitted against Kama and Undertaker defeated him in a casket match.
8 Evenly Matched With The Mastodon
The Undertaker hasn't always had good feuds with big men but Vader was a very good rival for Undertaker. They clashed at the 1997 Royal Rumble with Vader earning a huge victory over the Phenom.
Vader began to be managed by Undertaker's former manager Paul Bearer. The Mastodon had a shot at Undertaker's WWE Championship at In Your House: Canadian Stampede, but he was unable to add the WWE Championship to his resume as Undertaker showcased his strength by finishing off Vader with a Tombstone Piledriver.
7 Double-Wide, Double Deep Casket
The Undertaker found himself back into WWE Championship title contention after his rivalry with Yokozuna began at Survivor Series 1993. Undertaker began to build a double-wide, double-deep casket for Yokozuna for their upcoming casket match for the WWE Championship at the 1994 Royal Rumble.
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The storytelling was great with Yokozuna deathly afraid of caskets. However, with outside interference, Undertaker lost his casket match to Yokozuna. There was unfinished business between the two, and they had another casket match at Survivor Series 1994 with Undertaker getting his revenge with a win.
6 Early Title Bout With Steve Austin
Surprisingly, The Undertaker and Steve Austin didn't have the best chemistry together when it was bell-to-bell, but their storylines were fantastic. At In Your House: A Cold Day in Hell, The Undertaker, and Austin clashed in their first one-on-one WWE Championship match on pay-per-view.
This was a solid match, and despite the Hart Foundation's presence at ringside, the Deadman finished off Austin with a Tombstone Piledriver in a successful WWE Title defense.
5 The Deadman Clashes With A Fellow Giant
The rivalry between The Undertaker and Diesel began at the 1996 Royal Rumble with Diesel costing Undertaker, the WWE Championship. It was tic-for-tact with both men costing each other WWE Championship matches, which led to the two giants facing off at WrestleMania 12.
Big Daddy Cool was on his way out of WWE to join WCW, but Undertaker and Diesel had an underrated contest on the Grandest Stage of Them All. Diesel could have won the match, but he refused to cover Undertaker with the Phenom regrouping and putting Diesel out of his misery with a Tombstone.
4 Hart And Soul
The Undertaker and Bret Hart were two of the biggest stars in the New Generation Era, and they had a couple of mouthwatering feuds over the WWE Championship. At the 1996 Royal Rumble, Undertaker executed the Tombstone on Bret Hart and he was closing in on the WWE Title, but Diesel had other ideas.
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A year and a half later, Undertaker was the WWE Champion, and the Hitman was a heel and he challenged Undertaker for the gold at SummerSlam 1997. Shawn Michaels was the special guest referee, and he accidentally nailed Undertaker with a steel chair which led to Hart becoming a five-time WWE Champion. They had a competitive rematch at One Night Only with Hart retaining by DQ.
3 That's Gotta Be Kane
Paul Bearer did a masterful job of setting up The Undertaker's rivalry with Kane. Bearer built up the monumental unveiling for months, and at Badd Blood: In Your House, it came to fruition with Kane making his debut and interfering in Undertaker and Shawn Michaels' Hell in a Cell match.
The majority of their rivalry took place in the Attitude Era and other eras, but the foundations were set in the New Generation Era. Undertaker and Kane's rivalry was one of the best in WWE history with fans intrigued by storytelling more so than some of their matches.
2 The Deadman Meets The Heartbreak Kid
The legendary rivalry between The Undertaker and Shawn Michaels gained traction at SummerSlam 1997 when Michaels cost Undertaker, the WWE Championship. The two legends had their first one-on-one match at Ground Zero: In Your House with the bout going to a no contest.
They were enclosed in the first-ever Hell in a Cell match at Badd Blood: In Your House with the winner moving on to face Bret Hart for the WWE Championship at Survivor Series 1997. They had a five-star epic with Michaels prevailing all thanks to Kane making his WWE debut and laying out Undertaker with a Tombstone.
1 The Deadman Contends With A New Threat & The Ending Of A Successful Partnership
On the Raw after WrestleMania 12, Mankind made his WWE debut and he became a thorn in The Undertaker's side. Mankind had early success against the Deadman as he beat him at King of the Ring 1996. However, the unthinkable happened at SummerSlam 1996, when Paul Bearer and Undertaker's five-and-a-half-year partnership came to a crashing halt with Bearer beginning to manage Mankind as he aided Mankind in winning the Boiler Room Brawl.
Undertaker and Mankind's feud was outstanding, and Undertaker began to flip the switch in their rivalry. They competed in the first-ever Buried Alive match which Undertaker won, and he beat Mankind at Survivor Series 1996. A few months later, Undertaker captured the WWE Championship, and his first WWE Championship title defense was against Mankind at In Your House: Revenge of the 'Taker. It was a superb match with Undertaker victorious, and they wouldn't touch base for a year.
