The Evolution of the Undertaker

The legend turned 49 yesterday.

Complex Original

Image via Complex Original

For those of you who don’t know (and really, for shame if this applies to you), WrestleMania XXX is two weeks away and one of the marquee matches is The Undertaker vs. Brock Lesnar. The Undertaker match has become one of the top spectacles of WrestleMania due to his 21-0 record at the event. ‘Taker is also the longest-tenured wrestler in the company, making his debut 23 years ago in 1991. So to get you primed for his match—and to celebrate his 49th birthday (which was yesterday)—let’s take a trip through the various milestones of the Dead Man’s incredible career.

1991 - The Debut

The Undertaker first appeared on an episode of WWF Superstars in 1990 as Kane The Undertaker (this name will be important later), but he made his official debut as part of Ted DiBiase’s team at the Survivor Series pay-per-view. He rocked the finest of mullets and purple under his eyes to give off the impression he was the walking dead. In keeping up with the traditions of 1990s horror movies, Taker eliminated the Black guy, Koko B. Ware, in about 30 seconds. Then he got eliminated by chasing Dusty Rhodes down the aisle to the back and getting counted out because dead guys don’t need to follow WWF rules.

Obviously. Still, Undertaker made his mark as a bad ass big man who didn’t get hurt. They probably could have driven that point home better by just letting him eliminate the other team by himself but what do I know? The match ended up with a pretty sweet one-on-one between Bret Hart and DiBiase that’s worth going out of your way to see.

Also of note: during his rookie year, he’d put his opponents in body bags after he beat them. Gully.

1991 - Winning The Title

Two things you should know here: Hulk Hogan had exactly one good match in the 1990s. This wasn’t that match. But that’s not important here. What’s important is that Hulk Hogan hardly ever lost throughout the whole decade, so it was a huge deal when The Undertaker, just a year into his WWF career, beat Hogan for the title at Survivor Series 1991. Who cares if he needed Ric Flair’s help to do it and that Hogan won the title back from him less than a week later? No one can take that win from him.

Also, you’ll notice if you’re watching along at home, that this match featured the late Paul Bearer as Undertaker’s manager instead of the red-faced televangelist Brother Love. Bearer would be a huge part of Taker’s career using the mystical urn to give him power. Also, Bearer’s “Ooooh Yeahhhh” was probably the best ad-lib in the game until Young Jeezy came along.

Seriously, though, this match stunk. It featured a five-minute long face grab submission spot and was just a way to build a Hogan vs. Flair match that WWF never made happen anyway. Pay attention, though, as Bobby “The Brain” Heenan makes a bunch of jokes about Hogan being paralyzed like the Detroit Lions’ Mike Utley—who was paralyzed from the chest down during a game just a couple of weeks earlier.

Oh, also, the Survivor Series pay-per-view took place in Detroit. Stay classy, WWF. Roddy Piper then compared the win to David Duke becoming president for you political pundits out there.

1992 - 1994 - So Many Bad Matches

In 1992, The Undertaker became a babyface and had a feud with Jake “The Snake” Roberts that culminated in a WrestleMania VIII win (his second). After that, everything pretty much goes downhill as Undertaker faced a cavalcade of cheesy villains from Kamala to fucking Giant Gonzalez, who was a seven-foot stiff with a spray-painted six pack body suit. They even have painted on ass cheeks for him because why not? Undertaker beat Gonzalez at WrestleMania IX by disqualification because Gonzalez used a chloroform rag during the match. Yes. You read that right. This match is worth watching just to see Gonzalez sell punches like you sell a punch from your preschool nephew.

This time period also saw the advent of Taker’s Casket Match* where the winner puts his opponent in a casket and closes it. These matches weren’t good either. The only real highlight during this time period was his feud with Yokozuna, which was a series of good old-fashioned hoss fights. When they squared off at Survivor Series 1993 as part of a four-on-four match, the crowd went crazy and I have to admit that I got amped watching them beat the hell out of each other. Yokozuna was a criminally underrated worker, by the way, and he and Taker had the crowd that night.

*There was also a casket match in 1995 between Undertaker and Kama—the martial artist who would later become a pimp named The Godfather—over Kama melting down Undertaker’s urn and using the gold to make a chain. I shit you not.

1994 - Undertaker vs Undertaker

I really didn’t want to ever believe wrestling was fake. If I could have lived my whole life thinking wrestling was real, I honestly think I’d be in a happier place. However, an eight-year-old David D. saw the writing on the wall when an angle featured an Undertaker “clone” that was bought by Ted DiBiase and used to carry out his acts of greed. (Oddly enough, this was the second clone-related angle the WWF ran in the '90s). The “real” Undertaker showed up to set the record straight and battle the fake for the 1994 Summerslam in, you guessed it, another bad match. In hindsight, the fake Undertaker looked nothing like the real one, which makes me feel even dumber for being so confused as a kid.

This match is most remembered for the vignettes leading up to it, featuring the late Leslie Nielson of Naked Gun fame going around investigating the whereabouts of the real Undertaker. It was pure, unadulterated camp.

1996 - The First Great WrestleMania Match

Many people remember WrestleMania XII for the Bret Hart vs. Shawn Michaels Iron Man match but I’ve always found it to be overrated and boring until the last 20 minutes (fight me, bro.) It’s one of those matches people say is great because they feel like they should say it’s great. But the actual best match of the night was Undertaker vs. Diesel, which was totally unexpected because Undertaker hadn’t had many great matches and Diesel was never a great wrestler.

However, this is the perfect big man match. They just looked like two badasses who tore up stuff and damn near killed each other. It’s one of my all-time favorite matches and I’ll watch it 10 times before I watch the Iron Man match. I don't care!

1996 - Mankind

You may have noticed a theme of bad matches here, but it wasn’t the Undertaker’s fault. He was always a crazy athletic big guy and the skill was evident, but he was stuck wrestling big monsters without even an ounce of Undertaker’s ability in the ring. That all changed when Mick Foley aka Cactus Jack debuted in the WWF as Mankind. He was the perfect foil for Undertaker, providing him with the best matches of his career to date and someone who didn’t mind taking a beating. The feud also led to Paul Bearer turning his back on Undertaker and joining Mankind.

The beef gave Undertaker the shot in the arm his career needed and allowed him to break away from those horrible monster matches he was having. And let’s not forget that they wrestled again in 1998 in a Hell In A Cell match, which saw Undertaker throw Mankind off of the top of a cell in what has become one of the most famous matches of all time. This is probably a top 10 feud of the 90s.

1997 - Hell In A Cell 1 and Kane

1997 saw Undertaker’s first five-star match as he took on Shawn Michaels in the first Hell In A Cell. While Shawn Michael was probably the best wrestler in the world at the time, Undertaker held his own and both showed their ability to have a great match—which we’d see again later in their careers.

The match, though, is also famous for the debut of Undertaker’s brother, Kane. The WWF, in full Attitude Era mode, ran an angle where it was revealed that Undertaker had a brother he’d thought was dead since he was kid—killed in a fire Undertaker himself set. Are you feeling the drama here? Paul Bearer, still feuding with Undertaker promised to have Kane appear and that promise came true at the Hell In A Cell match. Kane broke into the cell and choke-slammed Undertaker to give Michaels the win.

Regardless of the ending (which is actually not as hokey as it seems written down), this match stood as the Undertaker’s best until he and Michaels faced off again a decade later. [/foreshadowing]

His feud with Kane would continue off and on for the rest of Undertaker’s career as the story got more convoluted and confusing. One minute they’d be teammates, the next they were feuding. They’ve wrestled at WrestleMania twice and also held the tag titles together. You just never know with these two kids. It does say something to the Undertaker character though, that there could be a guy who basically does most of the same moves who could also have a long career as well.

1999 - The Ministry Of Darkness

Attitude Era Undertaker went full-on cult leader in 1999, leading a group of wrestlers (Edge and Christian, The Acolytes, Mideo, Viscera among them) in a faux-satanic rampage on the WWF. He talked of serving a “higher power” (that ended up being Vince McMahon in one of the dumbest twists of the time) and kidnapped Stephanie McMahon during an episode of RAW. As leader of the Ministry, he beat Stone Cold Steve Austin at the Over The Edge pay-per-view for his third world title reign. The Ministry Undertaker was cut short, though, as an injury sidelined him for the rest of the year.

The most notable and bizarre moment from this era was Undertaker’s match with the Big Bossman in a Hell In A Cell. Yeah, this match was trash, but it ended with Taker setting up a noose and hanging Bossman from the cage. That happened.

2000-2003 - The American Badass

The Dead Man gimmick had run its course and seemed out of tune with the more realistic-ish characters in the company. So he abandoned the dark persona and came to the ring with leather pants, a wife beater, a motorcycle and a Limp Bizkit theme song. Heh. Limp Bizkit used to be a thing. Never forget.

During this time, though, Undertaker had to deal with a lot of injuries that kept his match quality inconsistent. He still had a classic ladder match with Jeff Hardy on RAW and another one of my all-time favorites against Ric Flair at WrestleMania 18. He also wrestled Hulk Hogan again in a title match that wasn’t any better than their 1991 bout. There’s a moment where Taker “choke-slams” Hogan and I swear it looks like a gentle shove. It’s an embarrassment.

This era also saw the first Undertaker vs. Brock Lesnar feud, ending in a Hell In A Cell match in which Taker bled like a stuck pig and made Brock look like a million bucks in the process.

This is also when the WrestleMania undefeated streak started to become a selling point. WrestleMania 17 featured a great match between HHH and Undertaker with a central theme being whether or not Triple H could end the streak. Of course, Undertaker won.

2004 - 2009 - The Dead Man Returns And A Wrestling Renaissance

WrestleMania XX saw the return of the Dead Man gimmick and Paul Bearer as the Undertaker took on Kane. Fans had been clamoring for the old Undertaker and we got it…thought it was a bit underwhelming with Taker’s short hair and a sub-par match against Kane.

It was a mostly-overlooked No Way Out 2006 that changed everything though. Undertaker wrestled Kurt Angle in what turned out to be one of their best matches. Undertaker started integrating MMA into his wrestling style and used this match to show it off. God bless Kurt Angle, who always had good chemistry with Undertaker and this match was no exception.

Undertaker would go on to have some of the best matches of his career. He put together some monster matches with Batista (yes, he did have good matches before turning into the tight-jean-wearing, Jordan XX8-loving, Shane Battier-headed goon he is now), a classic WrestleMania main event with Edge, and some matches with the Great Kha.

2009 - Present - Semi-Retirement and The Greatest Match Of All Time?

I dare you. I double dipset dare you to watch Shawn Michaels vs. The Undertaker from WrestleMania XXV and not get fully invested. This is a top five WrestleMania match of all time and any opinion otherwise is for stupid people. Eventually, Undertaker would only show up right around WrestleMania to have his matches and a few months after then leave until it’s time to build up his next threat to the Streak. He doesn’t have anything to prove as he winds down his career, presumably with a final match against John Cena at WrestleMania XXXI next year…but who knows? He may just be around forever.