By Will Pruett

In anticipation of WrestleMania, we'll be reposting this series with a new section covering Undertaker's 21st WrestleMania win appearing on Saturday.

This is where the younger version of myself joined The Streak in progress. I remember leaving notes and VHS recordings of Raw for my brother (ten years older than me and the original ignitor of my wrestling fandom) that worked the graveyard shift discussing Undertaker’s pre-WrestleMania XIV return. I remember sitting on the floor of his room as we watched WrestleMania XII on home video. I'll never forget these matches or the memories made while watching and rewatching them.

The journey that is The Streak was definitely enhanced in these years. None of these matches are pointless squashes. This series of matches helped to shape me as a wrestling fan. These years are the ones that created my original images of The Undertaker.

WrestleMania XII - Undertaker vs. "Big Daddy Cool" Diesel:

This match begins the rise of The Streak. It is now moving into the semi-main event, where it stays for quite a few years (including one brush with the main event). This is also the first good match in The Streak, which I suppose is well worth noting.

The parade of large opponents for Undertaker continued at this WrestleMania. Lucky for him, this large opponent is more skilled than anyone he has faced yet (with the exception of Jake Roberts). This feud was built around matches each man had with Bret Hart at the pay-per-views preceding WrestleMania. They had cost each other the WWE Championship and were meeting on the grandest stage of them all.

1996 could be considered the most important year of Undertaker's career. This is when he went from a specialty gimmick to a talented wrestler. While there were glimpses of his agility and skill before, he put it together in 1996 beginning with this match and continuing throughout the rest of the year (especially in his feud with Mankind).

Across the ring from Undertaker is Diesel, or as he is known today, Kevin Nash. Nash had been WWE Champion for most of 1995. He seemed to be on top of the world and had just undergone a recent heel turn, giving him a deluge of fresh opponents. He had also just committed to a contract with World Championship Wrestling and would be leaving one month after WrestleMania.

The Undertaker entered with fog, lights and Paul Bearer. This would be Bearer's last appearance with him until 1999. Vince McMahon is in full on hyperbole mode calling this match "The Gravest Challenge" and "The Battle of the Monsters."

While today we do not look at Kevin Nash as a paragon of wrestling skill, he definitely worked hard in this match. Nash and Undertaker had the big man match that Undertaker had probably been waiting to have for many years. They both could move pretty well and Undertaker had grown to the point that he could bump around for Diesel. They also executed a really nice double big boot spot in the middle of the match that bears mentioning.

Even though Diesel was planning to leave shortly after this match, he was still kept strong. He would face new champion Shawn Michaels at the next pay-per-view and needed to look like a legitimate contender. This is why Diesel was slow to pin Undertaker after two Jackknife Powerbombs. The finisher kick-out is a major factor in The Streak. It began with Jake Roberts' DDT and continued here.

Undertaker eventually did what he does best and gave Diesel a Tombstone Piledriver for the pin. This was the first WrestleMania Tombstone since WrestleMania VIII.

The coincidence here comes into play with Nash signing with WCW before this match. If the idea originally was to get the new heel contender over for his eventual title match, why would WWE have him lose? It is fairly strong booking theory to put a heel over in the semi-main event if a babyface will be champion at the end of the night. If Nash had never signed with WCW he easily could have beaten The Streak and left Undertaker at 4-1.

WrestleMania XIII - Undertaker vs. "Psycho" Sid:

For those wondering, I have no intention of spelling the word "Psycho" the way WWE did in 1996 and 1997.

This match came as a result of a whole lot of upper-card shuffling in the months leading up to it. Shawn Michaels lost his smile and his knee. Bret Hart won and lost the WWE Championship in the span of two days. Undertaker went from being eliminated from the Royal Rumble to challenging for the championship out of nowhere.

This was the lowest selling WrestleMania of all time. WWE’s business was down at the moment and the loss of the number one babyface (Shawn Michaels) did not help things. They needed someone consistent with a deep connection with the fans to build around. The eye of Vince McMahon turned to The Undertaker to get him through this troubled time.

Before this match Shawn Michaels made a full entrance, milked the crowd with a couple of laps around ringside and finally settled in at the commentary table. This is the first match in The Streak that Michaels would be involved in.

Undertaker made his entrance first which is a rarity at WrestleMania. He went old school with gray gloves. This match does adhere to the aforementioned rule concerning ‘Taker in gray. The Streak is once-again mentioned as he entered. At this point it's an arbitrary stat like “Undertaker has never lost in Chicago” would be.

Sid was at the highpoint of his career. After a couple of surprisingly good matches with Shawn Michaels at Survivor Series and Royal Rumble he won the title the night after Bret Hart won it. The "Master and Ruler of the World" was trying hard, but the connection still was not there.

This match was a No Disqualification match, making it the first stipulation match of The Streak. It was also the first championship match of The Streak. Another first in this match was Undertaker receiving the Tombstone Piledriver from his opponent. Triple H and Kane would also make him feel his own finisher in the years to come.

The start of this match was supremely awkward as the bell rings and Bret Hart suddenly ran to the ring to cut a promo on how he should be the champion. This was the first of three times that he interfered in the match. Did I mention that the main event scene was a mess?

This match feels a lot like the match with Diesel did. They repeat many of the spots that worked a year earlier. Much like Diesel, Sid rocked the Powerbomb. Much like the match with Diesel, they did a double big boot spot. Unlike the match with Diesel, the level of passion from the fans was quite low.

Undertaker managed to overcome the mediocrity of the match and Sid when Bret Hart runs in and distracts Sid, leading to a Tombstone and an Undertaker celebration.

With the Michaels injury WWE was panicking and they put the title on their most consistent number two star. This was an odd time for the company as they were close to falling apart. Even without the championship, Sid vs. Undertaker was the likely match (although some rumors do include Undertaker vs. Steve Austin). This was quite the poor match and an unenjoyable experience to relive. Who knows what the fallout towards The Streak would have been if the scheduled Michaels vs. Hart match had taken place.

WrestleMania XIV - Undertaker vs. Kane:

When WrestleMania XIV is discussed amongst longtime fans the “Austin era” is usually the thing they think of first. Indeed, this show did begin that era with Austin’s victory over Shawn Michaels. However, when I think of WrestleMania XIV, I think of Undertaker and Kane.

This was undoubtedly the best built match on the show. From the moment of Kane’s debut at Badd Blood: In Your House in October this match seemed destined to happen. Although Undertaker swore he would “never fight his own flesh and blood” this match was on everyone’s mind.

At the Royal Rumble that year Undertaker was locked in a casket and Kane set it on fire. Undertaker was not in the casket when it was reopened and he would not appear until March. On Raw that night he confronted his brother and said the fires of hell could not keep him from this match.

Was it cartoony? Of course it was. Was it a well-produced angle that captured my imagination and made me stand up and cheer? Yes, yes it was. This lead to the actual match, which began with Pete Rose (playing a heel to the fans in Boston that night) being Tombstoned by Kane (also a heel). I will never forget Jim Ross yelling “That's Pete Rose!” as long as I live.

Undertaker’s entrance was a thing of beauty. The Druids were out first, making their debut, with their patented fire sticks. Undertaker then walked slowly, ominously to the ring with the first of his enhanced WrestleMania outfits on. This is the entrance I always will remember. This moment and this entrance were stunning.

What helps the entire atmosphere is that this is the first encounter between these two men and it is undoubtedly the best. They pull out all the stops to make this a memorable WrestleMania match. Undertaker breaks out his first dive over the top rope here, which should show just how important this is. Much like at WrestleMania XXV and WrestleMania XXVII he almost kills himself doing this. Be careful Deadman.

This is a different match against a monster heel than his last four at WrestleMania. While he does do a fair amount of selling, he is not dominated. This feels like a big fight between two evenly matched boxers. Jim Ross and Jerry Lawler do a masterful job selling it as such.

It takes three Tombstones to finish Kane. This is the first time one did not get the job done. Kane is up after the match and along with Paul Bearer he attacks Undertaker, Tombstoning him on a chair.

This match is monumental. The evolution of The Undertaker from 1996 to 1998 culminated here. Steve Austin may have been the lead babyface at the time and this may be remembered as his night, but this was also one of the defining moments of Undertaker’s career.

WrestleMania XV - Undertaker vs. Big Boss Man in the Hell in a Cell:

While this match may not be the worst in The Streak, it is my least favorite. There are so many reasons for that. 1999 was an odd year in WWE. While they were at the peak of their popularity, they were in a creative downward spiral. Vince Russo's shades of gray booking had watered down most of the characters in the company, with Steve Austin being the last semi-honorable man.

I'll attempt to recap the odd story going into this feud. The Undertaker was coming off of his endless feud with Steve Austin. After losing a Buried Alive match to Austin at Rock Bottom in December he returned as the "Lord of Darkness" with Paul Bearer at his side. This new incarnation of Undertaker stretched the character from dark to downright satanic.

Undertaker entered into a feud with Vince McMahon, leading his Ministry of Darkness against McMahon's Corporation. Both of these were heel groups. McMahon's children were kidnapped by Undertaker and odd crucifixions were attempted. This was concurrent with Steve Austin's war with McMahon.

In an effort to make this match more attractive the Hell in a Cell stipulation was tacked on. This was just nine months after Mankind and Undertaker defined Hell in a Cell at King of the Ring 1998 and there was a certain level of violence expected. This match did not deliver on that, or any other standard.

Undertaker's entrance lacked Druids and fire, but it did feature an amazing cape with large shoulders. This cape is the best thing about the match. In his own theme music you can hear Undertaker saying "turn yourself over to the lord of darkness" and speaking Latin. Did I mention they were going the satanic route?

The less said about the actual action in the match, the better. Every gimmick they tried did not work as planned. Boss Man handcuffed Undertaker to the Cell and beat on him with a nightstick. This would have been great, but the handcuffs broke before they were supposed to and Undertaker was prematurely freed.

This is the first time Undertaker bleeds at WrestleMania. This blood is a feeble attempt to wake up a crowd that has clearly realized that silence is golden. Mercifully, this match is short and ends with a Tombstone and a pin. Unmercifully, this would not be the end of the segment.

As Undertaker celebrated in the ring, The Brood (Gangrel, Edge and Christian all making their WrestleMania debuts) lowered themselves from the rafters to the top of the cell. They lowered a rope with a noose tied at the end into the cage, then re-ascended to the rafters. Paul Bearer began to raise the Cell, which raised the rope and the Boss Man. Michael Cole yelled "Is this symbolic?" as a man was literally hung in the ring. This is the only time the word "literally" should have been used and was not in wrestling history.

Everything about this match was bad. Undertaker had begun his second regression as a worker. Boss Man was never that great to begin with. The Hell in a Cell was tacked on and neither man was willing to do the work to make this stand up to the Shawn Michaels and Mankind versions of the match.

When Undertaker would begin his second long absence in September 1999 it could not come soon enough. The character was in need of a change.

The Verdict at 8-0:

This fifth of The Streak was very hit or miss. The Undertaker had clearly grown as a worker, but that was dependent on the opponent. He couldn't exactly carry anyone to a great match, but placed in the ring with a half-way decent worker (like Diesel or Kane) he could have an exciting match. It is amazing to see his growth leading up to 1996 and his regression as 1999 struck.

This chapter of The Streak saw some transcendence, but it also pushed the limits as to where Undertaker's character could go. We really saw his Deadman character killed off due to the illogical extremes it ventured upon. WrestleMania XV would be the last WrestleMania for the Deadman for five years. Undertaker's next evolution would create a stark contrast and will be the subject of part three.

Let's do some good old fashioned talking about this blog and Undertaker's Streak! Feel free to email me at itswilltime@gmail.com or to follow me on twitter at twitter.com/itswilltime.

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