Through Real Americans and Macho Men – through Hitmen and Heartbreak – through Rattlesnakes and Brahma Bulls – through Games and Olympians – through Animals and, uh, Cenas – through Vipers and Beasts…we could always depend on one.
Through it all, one name has remained as a fixture in WWE – The Undertaker. For 25 years now, The Dead Man has been the mainstay that has earned him the moniker of being referred to as “The Conscience of the WWE.” There aren’t too many that have walked through a WWE curtain that have earned the level of respect that The Undertaker has, both from the fans and the locker room.
If you want respect, you go through The Undertaker. If there is an issue between two guys backstage, it’s settled by The Undertaker. If The Undertaker gives you advice, you take it as gospel.
This years’ Survivor Series marked the 25th anniversary of his debut. If there was a checklist of things you would want to do in a wrestling career, The Phenom could have probably checked everything off of that list – possibly at least twice. In Ric Flair’s Hall of Fame induction, Triple H said that Flair didn’t just deserve the Hall of Fame honor, he deserved his own wing. Hard to argue the same for The Undertaker.
So let’s take a look back at those 25 years – the up’s, the down’s, the rivals, the allies, the evolution of the character and the road that has led us to where we are today…25 years later.
Year 1
The debut of The Undertaker was shrouded in, well, what else? Mystery! “The Million Dollar Man” Ted DiBiase advertised a “mystery partner” to join him, Greg Valentine and the Honky Tonk Man to take on Dusty Rhodes, Koko B. Ware and The Hart Foundation at the 1990 Survivor Series. DiBiase made the introduction, Brother Love brought him down to the ring as his manager (for some reason) and the rest is indeed history.
The first year for The Dead Man was flooded with Hall of Fame interaction. The infamous WrestleMania streak began at WrestleMania 7 in 1991 against Hall of Famer Jimmy “Superfly” Snuka (I guess we should call him a Hall of Famer now before the verdict comes in and referencing Snuka becomes as awkward as referencing Chris Benoit). After that the Hall of Fame journey continued with a short program against The Ultimate Warrior, an alliance with Jake “The Snake” Roberts and then working with The Immortal one himself, Hulk Hogan. How did THAT program turn out for The Undertaker you ask?
Year 2
It turned out pretty good! One year after debuting, The Undertaker found his way into the WWF Championship match against Hogan at the 1991 Survivor Series. 
With a little assistance from Ric Flair (what do you know, another Hall of Famer) The Phenom win his first Championship. Unfortunately the run was short-lived as Hogan won the rematch less than a week later and took the title back. It was odd to see a major pay-per-view show seemingly completely used to promote another random pay-per-view special later in the week. Regardless, bot Survivor Series and This Tuesday in Texas were centered around The Undertaker and the WWF Championship. The Dead Man had officially arrived.
We then saw the lighter side of the dark side when Taker threw away his alliance with Roberts when he grabbed a chair away from Roberts that was meant for Miss Elizabeth. This led us to the second WrestleMania win over Roberts at WrestleMania VIII. After that, it was on to a battle with the Ugandan Giant Kamala as one of the headlining matches at the 1992 Summer Slam in front of over 80,000 fans in London.
Year 3
The rivalry with Kamala continued into the Survivor Series and led to the introduction to what would be a specialty of The Undertaker – the Casket Match. This first match actually used the old school coffin that Taker actually had to nail a lid shut as opposed to just closing the lid. Kamala’s manager was upset that his man lost and promised a giant surprise for The Dead Man. That surprise came in the form of the 7’7” Giant Gonzales. This gave us what many consider to be the Dead Man’s weakest WrestleMania match against Gonzales but still came out with the win, obviously. It’s probably just because I was an awe-struck nine-year-old amazed by a man that size, but I may have been the only one entertained by this giant. Ah well, him and his furry feetie pajamas are fondly remembered by this writer.
Year 4
Taker was used as a bit of an injury fill-in in the 1993 Survivor Series, but this match launched what would be a strong rivalry with The Dead Man and the massive 500+ pound WWF Champion Yokozuna (yep, Hall of Famer). The two brought the casket match to the 1994 Royal Rumble for the title. It took a group of other WWF Superstars to do it but The Undertaker was stuffed in the coffin. The aftermath was, at the time, probably one of the most interesting segments produced up until that time. A mysterious smoke started spewing from the casket and The Undertaker, in the casket, appeared on the video wall to deliver a message that he will NOT rest in peace…though we didn’t see him again for seven months. And when he came back, we got the big much anticipated Undertaker vs Undertaker match. For those reading this finding out about the history of The Undertaker, this is not a typo, this was a thing.
Year 5
The 1994 Survivor Series brought us the rematch from the Royal Rumble against Yokozuna. Another casket match but not for the title. Fans were assuming that Yokozuna would just use the same tactics as before and higher a group of guys to help put the Dead Man in the box. So, how do you keep the large group of superstars away from doing the same thing that they did at the Rumble. Well there is only one logical answer for that…Chuck Norris. Yes, Chuck Norris. The rest of year 5 was spent going up against Ted DiBiase’s Million Dollar Corporation. 1995 wasn’t exactly the most entertaining year in WWF history, so we’ll move on.
Year 6
1996 picked up the ball that 1995 dropped with a strong program between The Undertaker and Diesel. Their match at WrestleMania was by far the most entertaining match that the Dead Man had at that point. The night after WrestleMania we were introduced to arguably one of The Undertaker’s biggest and most intense rivals – Mankind. The two would give us countless battles and memorable brawls like the inaugural Boiler Room Brawl at the 1996 SummerSlam and the first ever Buried Alive match. Unfortunately, thanks to the efforts of The Executioner, Taker was the one who was buried alive. Side note – did you know that The Executioner was Terry Gordy? So, to summarize, WWF gets Terry Gordy and make him The Executioner. WWF gets Michael Hayes and make him Dok Hendrix. Here’s a fun game – try to guess what horrible 90’s gimmick they would have given Buddy Roberts if they rounded out the Freebirds – I’m going with some kind sinister politician.
Year 7
After being buried (a statement that can only make logical and legal sense in sports entertainment) The Undertaker made his return against Mankind at the 1996 Survivor Series flying down from the Madison Square Garden rafters in a leather bat costume…glad that one didn’t stick around. For the next few months after that, the WWF saw a lot of confusion – mostly centered on a certain smile being lost. Regardless of how it came about, the end result was that WrestleMania 13 in Chicago ended with that familiar purple glow and The Undertaker holding the WWF Championship high as he started his second reign as champion. After a few underrated matches with the likes of Stone Cold Steve Austin (Hall of Famer), Farrooq (Hall of Famer) and another battle with Mankind (who, if you haven’t heard, is in the Hall of Fame), Taker found himself in a heated battle with Shawn Michaels after Michaels cost Taker to lose the title to Bret Hart in a classic match at SummerSlam.
This took us to The Undertaker once again participating in a match unveiling a few months later. Taker and Michales were the first to step through the doors of the Hell in a Cell and set the bar pretty high! The match itself was extraordinary, but the biggest impact in The Undertaker’s career came when the lights went out towards the end of the match. After months of claims, Paul Bearer came to the ring – and with him was this monster…who was big…and was in red…’cause he was a big red monster…Kane, I’m talking about Kane! This was 1997, and as we saw this past Survivor Series, the connection between the two characters is still strong 18 years later.
Year 8
Kane’s debut was the start of the buildup for a WrestleMania 14 match. After months of Kane challenging Taker to a fight and Taker saying that he would never fight his brother, The Phenom finally succumb to the challenge and accepted at the Showcase of the Immortals. I guess being locked in a casket and having said casket set on fire is apparently a breaking point for some. The two spent the next few months going at it, including another match innovation with the Inferno Match. But obviously this led to the two forming an alliance shortly thereafter in hopes of taking the title from Steve Austin. Welp, that didn’t work all that well.
Year 9
In late November of 1998, a recently reunited Undertaker and Paul Bearer failed at their attempt to embalm Steve Austn and in response Austin won a match where he buried The Undertaker alive…
…
(want to give some time to let that sentence sink in)
…
After the “resurrection” of The Undertaker, we saw another metamorphosis in the character of The Undertaker. A change that saw Mark Callaway “believe he was the character that we was playing” and became “The Lord of Darkness.” Taker and his newly formed faction “The Ministry” gave us several eerie moments throughout the first half of 1999 in hopes of taking control of the WWF from Vince McMahon. That was until it was revealed that it was just an elongated plot by Vince to get back at Stone Cold. During this time though, while it was a short one, The Undertaker did claim his third WWF Championship – although the title win came on a night where the matches were the last thing on all of our minds as we lost Owen Hart. The Undertaker would then spend a few months as a bit of a teacher/mentor towards one of the WWF’s newest stars, The Big Show. Then, late in 1999, The Undertaker would disappear…
Year 10
8 months would pass with no sign of The Dead Man. Then in the summer, we would start seeing cryptic vignettes that really didn’t have a direct message let alone that The Undertaker was coming back. Then at Judgment Day, as DX and the McMahons were attacking The Rock towards the end of the main event Iron Man Match for the title against Triple H, that same cryptic promo appeared on the big screen, only this time it ended with a simple “…now BACK from the dead – He’s Here!” Ladies and Gentlemen, I give you The American Bad Ass! 
The Undertaker came down to the ring on his motorcycle dressed in more Mark Callaway-friendly biker garb. Complete with a bad ass Kid Rock entrance song, this was by far an Undertaker that we had NEVER seen!
Year 11
The Bad Ass continued to be, well, bad ass through the end of 2000 – mainly by shoving Rikishi off of the top of the Hell in a Cell – and into 2001. In my opinion, one of the most underrated matches of The Streak took place at WrestleMania 17 against Triple H. Spoiler Alert – Taker won! From there The Undertaker, already known as a locker room leader, became one of the leaders for the WWF against the efforts of the new WCW/ECW Alliance.
Now I understand that this was a WCW contingent that didn’t include WCW mainstays such as Sting, Ric Flair, Lex Luger, Goldberg or the nWo-but I was a huge mark in the summer of 2001 during The Invasion. I still say that the night of the “merger” between the two failed companies was one of Raw’s most memorable moments. I’ll never forget the excitement I felt when I realized that Taz, Rhyno, Raven, Justin Credible and The Dudleys were attacking Chris Jericho and Kane because ECW was back! I’m pretty sure we won’t see anything like that again…even when the inevitable happens and Vince buys out TNA for about $206…and change.
Year 12
After The Alliance was vanquished, Taker took out some frustrations on good ol JR and became a heel. I don’t know what was worse at the time, attacking Jim Ross…or The Undertaker with a crew cut! Well it worked for him as he went on in 2002 to seemingly resurrect Ric Flair’s wrestling career at WrestleMania and then defeated the returning Hulk Hogan to hold the Undisputed Championship once again. Later in the year, The Undertaker was so important in launching the career of a young rookie who had just won the title and needed to be established as a true force. And after beating and bloodying The Undertaker, Brock Lesnar became just that!
Year 13
2003 was a bit of a slow year for the American Bad Ass, spending most of the year going against The Big Show and A-Train. Late in the year though, he started a program against Vince McMahon which would culminate at the Survivor Series …
Year 14
Year 14 started off with an end…which turned out to be a new beginning. At the 2003 Survivor Series, thanks to Kane, The Undertaker once again lost a Buried Alive Match. I remember saying to a friend of mine shortly after that match…”hey…have you noticed that Taker has started to let his hair grow out a bit? You don’t think that…you know, I do think that…” And it happened! With Kane in the ring at the 2004 Royal Rumble, the crowd started the famous 10-second countdown, the horn sounded, and the lights went out as that familiar sound of the tolling bell sounded and the crowd erupted! While it was just a tease that night, and we would get a couple more months of teasing, WrestleMania 20 would indeed be “Where It All Begins…Again!” The much-missed shrill sound of Paul Bearer’s “OOHHH YEEEEEEEESS!” led the return of what fans had been clamoring for for months…the return of The Dead Man! The year was spent reintroducing the WWE Universe to eeriest character in history. This was done flawlessly…well…with the exception of putting Paul Bearer in a box and filling the box with concrete for some reason. Eh, nothing’s perfect.
Year 15
Much like he did with Brock Lesnar, Taker would spend most of 2005 putting over another young rising star set for greatness – Randy Orton. Orton had won his first World Title at SummerSlam 2004 after beating Chris Benoit Santa. Orton still needed to get over the hump to stay towards the top of the card and he did so with a classic match with The Dead Man at WrestleMania 21. The two would go on to have great matches throughout the year. In October 2005, Orton and his dad Bob Orton Jr. (Hall of Famer) decided to “pull a Kane” if you will and lock The Phenom in a casket and set it on fire. That’s the way to eliminate The Undertaker for good, right?
Year 16
WRONG!!! At Survivor Series in 2005 after Orton was the sole survivor in the main event match – the bell tolled, and a casket was brought out to the stage, started on fire and Taker jumped out to let Orton know that he didn’t get the job done. The two ended their yearlong rivalry in Hell in a Cell the following month. The title was then in Taker’s sites again as he challenged Kurt Angle. The two had what I consider to be the most underrated match possibly ever! Seriously, if you pay you’re $9.99, jump on to the WWE Network and pull up No Way Out 2006 – you won’t be disappointed in the main event! After that it was a pretty slow time for Taker going up against guys that needed the “face The Undertaker” boost – Mark Henry, The Great Khali (who actually was pretty bad ass when he debuted) and Mr. Kennedy.
Year 17
The Dead Man came back to the main event scene in 2007. The year started with Taker becoming the first man to enter the Royal Rumble at #30 and win. His last elimination came with after an epic battle with Shawn Michaels. Boy, wouldn’t it be great to see those two in a match again? Don’t you think it could possibly steal the show??? (#Foreshadowing) The Dead Man used the win and started what I consider to be a very underrated rivalry with Batista. The two stole the show at WrestleMania that year as World Heavyweight Championship belt was around The Undertaker’s waist for the first time. The title was taken away after Edge (Hall of Famer) cashed in his Money in the Bank contract after a steel cage match draw between The Undertaker and Batista. Do yourself a favor and YouTube the end of that match and see how the two men climbed out of the cage and landed on the floor “at the same time.” Love that WWE set up a split screen where you can clearly see that it wasn’t anywhere near the same time.
Year 18
Edge would once again cost The Undertaker the title inside Hell in a Cell against Batista at the 2007 Survivor Series. This took us to an amazing match between Edge and Taker to main event WrestleMania 24 in 2008. The two would take their rivalry through a TLC match and finally a Hell in a Cell match themselves at SummerSlam 2008 where Taker chokeslammed Edge “to hell.” I love how “hell” is always just under the ring. Taker chokeslammed Edge through the ring…to hell. Back in the day The Big Show did the same thing to Taker and sent him “to hell”. So apparently Hornswoggle and the Little People’s Court are in Hell too?
Year 19
“Sometimes it’s hell trying to get to heaven!”
It was this piece of advice in a surprising confrontation between Taker and Shawn Michaels at the 2009 Royal Rumble that planted the seed for what would turn out to be the finest moment in two illustrious careers. The 25th Anniversary of WrestleMania was the host for what many, including me, consider to be the greatest WrestleMania match ever – if not the greatest match ever. 
The match was the perfect storm of professional wrestling elements – two legends, the biggest stage of the year, the streak, etc. It’s a match that will be talked about for ages. We still talk about Savage/Steamboat at WrestleMania 3, this will be right along those lines. After that The Dead Man finished his year with an impressive program with yet another up and comer that needed to be established – CM Punk. The end result saw Taker holding the World Heavyweight Championship once again.
Year 20
At Elimination Chamber 2010 we saw another amazing feat from The Undertaker, but for a different and unexpected reason. Taker was the last man eliminated from the main event Elimination Chamber match by Chris Jericho after Shawn Michaels cost The Phenom the match, and his title, in hopes for a WrestleMania rematch. The impressive part? Thanks to a huge miscue with the pyro during his entrance, The Undertaker was literally engulfed in flames and wrestled the entire match with second degree burns! Another amazing example as to what the man would do to put on the show that the fans paid for. The rematch with Michaels had no chance of matching what the two did the previous year, and it didn’t. From there, writers were apparently out of Undertaker ideas, so they put him with Kane again. Always the fallback plan.
Year 21
In early 2011 we saw some cryptic vignette of an old rickety shack in the middle of nowhere during a strong storm with 2.11.11 at the end. Obviously this meant someone would appear on February 11th, and it ended up being The Undertaker – who hadn’t been on TV since the previous fall. I won’t lie, I was a little disappointed. The way it was set up and with rumored contract issues with TNA, there was a strong rumor (as there always seemed to be around WrestleMania time) that this would FINALLY be the WWE debut of Sting…well…it wasn’t. Taker and Triple H ended up having a solid match at WrestleMania 27, which ended up being one of the worst WrestleMania’s in recent memory – that’s what happens when The Miz is in the main event! It was at this point that we started the “one and done” Undertaker schedule. When you put as much time, effort and dedication as The Undertaker had over the past two decades, you’ve more than earned that privilege.
Year 22
We didn’t see The Undertaker again until the build-up for the following WrestleMania in a rematch with Triple H…with Shawn Michaels as the ref…inside Hell in a Cell. More perfect storm clouds found their way to Miami that night. Billed as “The End of an Era” the match turned into one dramatic spot after another with perfect use of the camera mics. You could feel the emotion of all three men inside that cage and you couldn’t help but cheer as the match ended and the three took their well-deserved bow at the top of the stage on the way back. Oh, and Taker won, by the way.
Year 23
Once again The Phenom took the rest of the year off until WrestleMania 29. We got another classic WrestleMania streak match – this time against CM Punk. The win put the WrestleMania record at 21-0. Boy I tell you, I could see this streak lasting forever…and ever…and ever…
Year 24
…WELP! Brock Lesnar had demanded a title match at WrestleMania 30 and demanded that a champion come to the ring and sign his open WrestleMania contract. Instead, Brock got the Dead Man! Surely, it would be more than he could handle! Or…uh… I’ll never forget – I’m watching the end of the match, I see and hear the three count, and I just sit still. Not in shock, but just waiting. I remember thinking “OK well the ref is now going to realize that Paul Heyman interfered in the match and DQ Br…wait, Heyman didn’t interfere. Oh, well then the ref will see the foreign object that Brock used and restart the match so tha…wait, there was no foreign object used in the match. Well…the ref will…” I noticed the infamous 21-1 graphic they put up in the SuperDome and it slowly started to hit me…holy s***, this is actually happening! The streak is over! At the time, it was beyond confusing to me. While I still don’t 100% agree with the “who,” seeing what they have done with Brock Lesnar and turning him into the monster that he has become – it’s hard to think that it could have been done to this level without using the end of the streak as the launching point.
Year 25
Once again we had to wait until the following WrestleMania season to get our Undertaker fill. This time it came with a challenge from a man that was looking to become “The New Face of Fear” Bray Wyatt. Taker accepted the challenge and beat The Eater of Worlds at WrestleMania 31. Months later, for the first time in years, we got an appearance from The Undertake outside of WrestleMania season as he cost Brock Lesnar the title at Battleground against Seth Rollins. Taker was looking for his revenge for the constant bragging of beating the streak. He got it…in a confusing way. The two had a great fight, not a match, a fight, at SummerSlam that Taker won…with a low blow? Heel tactics? Were they turning The Undertaker? No, no they weren’t. And that was that. The two had the rubber match that Brock won inside Hell in a Cell. After which Wyatt came for his revenge as he sent his Family to attack and abduct The Dead Man.
And that took us November’s Survivor Series and the start of Year 26. With Wyatt and his entire family involved in taking the Undertaker, and the next night Kane, away it was clear to see that a traditional Survivor Series match was on the horizon with the Wyatt Family taking on The Undertaker, Kane and two mystery opponents. Or, you know, not. The Dead Man and his brother ended up defeating just two members of the family, Bray and Luke Harper, in a match that seemed pretty lackluster and was all about nostalgia. Nothing wrong with that but so much more could have been done.
It’s seeming like year 26 may indeed be the last as all of the stars are aligned for The Phenom to hang up his boots at this year’s WrestleMania. The streak is over, it will be in his home-state, the show should have more people in attendance than any WrestleMania before it – it all just makes sense.
The question now is who will be on the opposite side of the ring with arguably the greatest WrestleMania performer of all in front of over 100,000 people? Will we finally get our Undertaker/Sting matchup? Will The Phenom end his career against the biggest star in the company these days, John Cena? Will Bray Wyatt get another crack at it? Only time will tell.
However the story ends, the beginning and middle have been nothing short of epic! Moment after moment, new match after new match, saying that The Undertaker is a big part of the history of professional wrestling and sports entertainment is a gross understatement. There were none like him before and we will never see any like him again! He has left us with hundreds of memories that will never rest in peace.
What was your favorite Undertaker moment? Let me know on Twitter @From_TheTopRope to join the conversation a quarter of a century in the making!
