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For over thirty years, The Undertaker was known for digging holes and taking souls. The WWE Universe loved him for it. But while the man was able to transcend and succeed throughout several different decades and eras, it wasn’t also black roses and funeral pyres for The Deadman. He was pitted against a lot of terrible and goofy gimmicks during the early years.

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The reason The Phenom was able to endure is that he actually is that good in the ring, and he always desired to learn more and get better. By his own admission, he couldn’t wait to get away from the pure zombie, slow-walking character, and be able to actually wrestle. It took a few years, but when he finally got the chance to work with the likes of Bret Hart and Shawn Michaels, The Undertaker started showing off just how good he was. Until then, he actually was just another gimmick character in the occupational-heavy New Generation.

Undertaker's Early Career Has Been Buried By The Times

Undertaker Vs Hulk Hogan

Ted Dibiase introduced The Phenom in an almost instantly iconic fashion. That plus The Funeral Dirge, and the fact that zero wrestlers looked like this guy immediately put all eyes on The Deadman. For the next year, the WWE followed the monster heel formula - feed any and all Journeymen to The Undertaker, take out future Hall Of Famer, Jimmy Snuka (which started The Streak), and eventually get to Hulk Hogan. But in a huge twist in the formula, there was no Big Boot-Legdrop to be found at their 1991 Gravest Challenge match.

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The Deadman walked away with the WWE title. If only for the week, the schmozz finish at Tuesday In Texas led to the WWE title being vacant and The Undertaker getting dropped from the WWE title picture for the next few years. Even though he defeated Hogan, he still dropped out of the main event picture like any other big nasty giant that the red and yellow monster had slain.

He Was Wallowing In Purgatory For A While

Undertaker Vs Yokozuna Royal Rumble 1994

While he was still adored by the fans and heavily featured, The Undertaker spent years drudging through a muck of storylines and wrestlers almost as slowly as he takes to get to the ring! After losing to Hogan, he had silly feud after silly feud. First was Kamala, whom we learned that the fearsome Ugandan Giant was deathly afraid of caskets, which led to the first-ever Casket Match (Coffin Match). He also dealt with a similar themed program with Yokozuna, which was far better; even though that contained the divisive 872 heels defeating The Deadman before he ascended to the heavens. Those were some of the better storylines Taker was involved in. The rest were good ol’ fashioned “lulz 90’s New Generation WWE.”

Death And Taxes

Undertaker Vs Kama SummerSlam 1995

For what seemed like years (and in a bad way), The Undertaker waged war against The Million Dollar Corporation. Stemming out of defeating The Underfaker at SummerSlam 1994, it wasn’t long before the real Deadman had to contend with the likes of IRS (at the Royal Rumble), King Kong Bundy (WrestleMania 11), and a few PPVs with his BSK buddy, Kama. The Supreme Fighting Machine had stolen The Urn and turned it into a big gold chain. He also had to work with a broken face, thanks to King Mabel crushing The Reaper’s orbital bone.

The Giant Gonzalez

Perhaps the biggest (no pun intended) and most egregious booking mistake was putting The Deadman against Jorge Gonzalez, aka The Giant Gonzalez. The former Atlanta Falcon began his wrestling career because Ted Turner noticed him on the Falcons and since he owned both the team and WCW, he brought him into the promotion. He was barely taught how to work there and things didn’t get better in WWE. While Taker had his first major WrestleMania entrance, nothing else good came from any of the matches or the program that transpired.

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The silly and head-scratching storylines stopped for the most part early in the Spring of 1996 when a certain mutilated Mankind debuted and was a new challenge for The Undertaker. About a year later, he was once again atop the WWE as the champion. The booking philosophies and storylines also began to shift gears, even the ones involving an undead zombie from beyond the grave.

Once Kane had debuted, the WWE had firmly entered The Attitude Era and there was no turning back for either The Phenom or the WWE. With the exception of hanging The Big Boss Man, the rest of The Undertaker in the nineties was worlds different from the mediocre early parts of the decade.