Top 26 Pictures That Show The Evolution Of The Undertaker

Mark Calaway, The Undertaker,, has had one of the greatest wrestling careers of all time. Starting way back in 1984 and continuing today in 2016 is a marvelous feat of endurance.

A key to his longevity is a willingness to update his gimmick to keep up with the times. His first Undertaker character fit in perfectly with early WWE good vs. evil tropes. It was a time when monsters were to be feared. As the '90s kept rolling, Vince McMahon was obsessed with occupation gimmicks, and The Undertaker technically fit under that umbrella as well.

When the Attitude Era came crashing in, storylines were able to go much further and we saw Calaway take his supernatural powers even further with his Ministry rituals and ability to return from matches that seemingly 'killed' him. When I think back on this time I fondly remember the many stables interacting in extreme premises. The Undertaker was right in the middle, leading the Brood, Acolytes, and eventually teaming up with the Corporation. To see Edge and Christain emerge from his posse must have made Calaway very proud, and to eventually feud with Edge for the World title would have been the cherry on top.

Kevin Nash has stated in a shoot inteview that he believed Calaway's American Badass gimmick was an advertisement to WCW that he could still be a valuable signing without the WWE-owned Undertaker gimmick. This was a time when brutal realism was being embraced and it made sense to take a break from his classic persona to preserve its freshness. That's a nice theory from Nash but I don't believe it myself. For one, Calaway remained fiercely loyal to Vince throughout their worst years. By the time he started riding out on the Harley (2000), WCW was already doomed.

Once Big Evil was buried, the hybrid Deadman returned and that's more or less what we've seen for the latter half of his career. He wisely chose the best pieces from his variety of gimmicks to create a badass Deadman with powers, personality, and MMA submission moves.

While it's still incredibly impressive that Calaway continues to deliver WrestleMania worthy performances year after year, since Lesnar at XXX, his age and fragility have become worrisome. I hold my breath when I see him struggle to stand up after tombstoning a big nasty heel. But for every Instagram photo of Calaway looking beyond his years, there's another of him working hard in the gym, prepping for his next appearance.

Will Wrestlemania 33 be his last? At this point I feel the fans are still excited to see him and as long as he has the drive to put the work in, I say he can do as he damn well pleases.

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26 The Old Soul

via wetalkwrestling.com

Mark Willian Calaway was born March 24, 1965 in Houston Texas (before his eventual move to Death Valley of course).

It’s rare to see a picture of Calaway smiling and what he mustered here hardly qualifies. If If I was the photographer I don't think I'd ask him twice. The term old soul definitely applies as this somewhat innocent looking child looks like he sees the decades of hellfire and brimstone ahead.

Or that could just be the red hair.

Calaway grew up with four older brother: David, Michael, Paul, and Timothy (none died in a fire). He grew up excelling at basketball and football and would eventually consider a serious career in athletics, though not choosing wrestling until a after high school.

25 Choosing a Path

via wrestlerap.com

It might not surprise you to learn that a big man with mobility would also be pretty good at basketball. Calaway played hoops for Texas Wesleyan University and was even offered an $80,000/year contract to play ball in Europe (where I believe they call it bouncey baskets).

If you've seen his smoking hot wife Michelle McCool, it definitely wont surprise you to hear that Calaway the basketball player was a hit with the ladies. His Texas coach Richard Hoogendoorn recounted "Everywhere he went, the girls were just all over him."

Luckily for wrestling fans (and his future wife), Calaway craved a life in the ring. He turned down the guaranteed money of European basketball and chose the much riskier path of professional wrestling instead.

With a mind-blowing 30+ successful years in the business, it's safe to say he chose the right path.

24 Texas Red

via weebly.com

Calaway debuted in 1984 as Texas Red in World Class Championship Wrestling. Like many rookies, he wore a mask in his first match and did the job for a more established veteran. Calaway was lucky enough to draw the legendary Bruiser Brody, but also unlucky enough to take a very stiff beating from the rough and tumble brawler.

This was worse than Wrestlemania XXX as Brody tied him up in the ropes and booted him in the skull repeatedly, picking up the win in just over three minutes. Brody was known to do what he wanted and that often meant physically punishing his opponents to make a point.

Calaway would spend the next four years with WCCW and the Continental Wrestling Association (known later as USWA after merging with WCCW). After paying his dues, he would eventually receive a golden opportunity from none other, than the King himself.

23 The Master of Pain

via youtube.com

Calaway adopted a gimmick as a former convict who spent four years in the Atlanta Penitentiary…for killing two men. I’d say he got off pretty easy.

He debuted this gimmick against poor Rodney Napper and squashed him even quicker than Brody did him four years before.

The best part is near the end of the slaughter, as a fan somehow holds out hope for the victim, yelling “get him Rodney!, Get him Rodney Now….get up Rodney…”. Rodney would not get up anytime soon. You could find this match on Youtube (after you read through this article of course).

Calaway showcased his impressive agility, performing a stellar leaping leg drop from a standing position, foreshadowing his victory over Mr. Legdrop himself, Hulk Hogan, just two years later.

But he would have to go through Jerry Lawler first.

22 First Title

via wwfoldschool.com

Looking like the American Badass, Calaway hit his stride with the Master of Pain gimmick, riding it all the way to his first Championship, defeating Jerry Lawler for the USWA Title in 1989. After five years of working the smaller circuits, Calaway was finally a World Champion (of a small region).

In the match, Lawler did his usual chicken heel act and started off having Dutch Mantel escorted out of the building by a doughy security guard. Lawler was a master of prolonging the action and building suspense.

Lawler was a very big deal down South so you know he wasn’t going to lose without all hell breaking loose. After nearly a dozen men came out from the back to attack the King (that Lawler still fended off), Calaway used this epic distraction to hit the champ with a foreign object and grab the win.

It wasn’t pretty, but he was the champ.

21 The Punisher squashes Steve Austin

via youtube.com

Calaway had even more biker leather and studs on than usual, but this gimmick had him wearing a mask. I can only assume this was a cross-promotional match and he wanted to prevent fans from recognizing him as the Master of Pain.

Austin was still long-haired-Williams at this point and did the job for Calaway. His only noticeable offense was an extremely long headlock, delivered like a true heel. Mike Rotundo would have been proud (and sweaty, boy was IRS sweaty).

Calaway not only smashed Austin in WCWA, but won that region's title as well, after Eric Embry forfeited the belt. Who would have thought these two would one day be WWE icons?

Calaway was ready for the big time, even if his next stop wouldn't make him a star.

20 1989 - “Mean Mark” Callous hits WCW

via wwenetworkplaylists.wordpress.com

The great Terry Funk came up with the name and it fit Calaway like an Undertaker glove.

Apparently Funk was the only one at WCW who knew what to do with the man who “never smiled” (according to incompetent WCW management).

Ole Anderson actually declared that Calaway would “never draw a dime”. Jim Ross argued to keep him, but Anderson had final say, and WCW decided not to re-sign the future pillar of the industry. How they lasted as long as they did is beyond me.

While in WCW, Calaway replaced Sid Vicious in The Skyscrapers, was managed by Paul Heyman, and laid a brutal beatdown to the Road Warriors. A nice start to his national career, but he would never reach the top of Turner's promotion.

He did get as far as challenging NWA Champion Lex Luger, but never wore their gold. Vince McMahon actually scouted that match, which fueled Calaway to participate even though he had a dislocated hip. The risk was worth it and he would be in the WWE by 1990.

19 1990 - WWE Debut at Survivor Series

via wwe.com

One of the greatest WWE careers of all time began at Survivor Series 1990.

After months of buildup, Ted DiBiase finally revealed The Undertaker as his mystery team member.

The “Million Dollar Team” must have spent most of their budget on The Phenom as I can’t imagine the other two members Honky Tonk Man and Greg Valentine (as Rhythm ’n Blues) costing more than $200 for the night.

He made an immediate impact with a vicious looking choke to Bret Hart off an irish whip. It was far more brutal than what fans were used to seeing.

He followed this by easily scooping up the bulky Jim Neidhart and then Tombstoning Koko B. Ware for a quick pin. The crowd was impressed and a star was born.

His gimmick was nearly complete, all that remained was the perfect manager. And I'm not talking about Curt Hennig.

18 Paul Bearer

via youtube.com

The Undertaker was originally managed by Brother Love, the incredibly obnoxious preacher gimmick of Bruce Prichard. Brother Love had experience managing heels but his bright red face and brash personality contrasted starkly with the deathly horror of the Western Mortician. It was just about the biggest mismatch imaginable between a manager and a wrestler.

Taker eventually got the former Percy Pringle as his manager, who adopted the persona of Paul Bearer.

The Bearer character matched ‘Taker perfectly and gave him a creepy mouthpiece. He also controlled the urn that contained The Undertaker’s supernatural power. The two would work together for decades to come, with only a handful of attempted murders between them. Without Bearer, it's very unlikely The Deadman character would have truly taken off.

Bearer was a pivotal piece indeed, “Oooohhh Yeessssss!”

17 Beating Hogan

via craveonline.com

From 1984 to 1990, Hogan had only lost the belt to Andre the Giant and The Ultimate Warrior.

In the first-ever one-on-one match at a Survivor Series, The Undertaker became the third to beat Hogan for the WWE strap.

‘Taker must have set a record for the most amount of choking done to the poor Hulkster. Choking in the ring, out of the ring, using the ropes, and even Paul Bearer got in on the choking when the ref wasn’t looking (twice!).

Of course it took some cheating from the dirtiest player in the game to seal the deal. Flair snuck a chair into the ring for Hogan’s head to be Tombstoned into and the match was over. Because ’Taker always performed his finisher safely, Hogan’s head was hilariously far above the chair, but all that mattered was the end result.

Although the crowd was cheering loudly throughout for Hogan, there was still a very positive response for Undertaker’s win. This was very rare to hear in those days of good vs. evil.

Hulk would win the belt back less than a week later at the disastorous This Tuesday in Texas, WWE’s first attempt at a secondary PPV. After two dirty finishes, President Jack Tunney declared the belt vacant, setting up Ric Flair’s incredible performance at Royal Rumble 1992.

16 Turning Face

via wwe.com

Jake Roberts had been embroiled in a deliciously evil feud with Randy Savage, even slapping Elizabeth in the face after their Tuesday in Texas match.

The Snake was about to take it much further by clocking Elizabeth with a steel chair when The Undertaker stopped him, turning face in the process.

To have such a creepy character as the good guy looked odd on paper, but the fans had been cheering him since the beginning and were more than ready to embrace him as a white knight. Taker would remain a face for the next six years, completely changing what the concept of a good guy was.

Snake and ‘Taker would start a feud that lead into WrestleMania VIII and the second victory of ‘the streak’.

15 The UnderFaker

via tumblr.com

Calaway is a tough son of a b*** who’s battled through many serious injuries over his long career.

One of his first injury breaks came after the Casket Match with Yokozuna, and WWE sent him off in style, booking a ring full of heels to finally get him sealed into the casket. Using some cheesy FX we saw The Undertaker 'from inside the casket!' proclaiming he would return and not “rest….in peace”.

Ted DiBiase claimed he had control of The Undertaker but fans would instead watch Brian Lee do a fairly decent impression. With the hair in his face I wouldn’t blame fans for believing it.

The fans at SummerSlam were definitely exhilarated to finally get the real 'Taker back, differentiated with new purple coloring, but the match was a slow dirge following an excellent Hart vs. Hart cage match. Couple that with the setup and tear down time for the cage and fans were probably ready to go home when this match finally got started.

It was a novel idea and they pulled it off. Let’s just hope they never do it again... Oh wait, they did.

via thegreenscreen.net

14 Phantom of the Opera

via wrestlestars.com

Calaway suffered a very real orbital bone injury near his eye and was forced to take time off for surgery and recovery. During a match with the green Mabel, the 450 pounder botched a clothesline, resulting in the injury to The Phenom. Yup, those were the kind of opponents 'Taker had to deal with in the mid 90s. Rey Mysterio would re-aggravate this injury many years later.

Despite the serious injury, the WWE was very weak at this time, and needed him to come back early.

Calaway, being the ultimate team player, donned the Phantom of the Opera mask at Survivor Series, wearing it until Bret Hart ripped it off a few months later.

The creepy mask fit his gimmick well and WWE did a stellar job of making the best from an unfortunate situation.

13 Lord of Darkness

via wrestlenewz.com

A feud with Mankind resulted in The Undertaker losing a “Buried Alive” match (he lost the majority of his own specialty matches). He would then return at Survivor Series with a vastly different look.

He descended from the ceiling with a bat-like cape, teardrop tattoo, and more gothic style. He was adding more personality not just to his look, but wrestling style as well.

He moved much more naturally than his previous ‘undead’ persona, and even broke out several submission moves. It also probably helped that the quality of his opponents in '96 and '97 were leaps and bounds over what he had before.

Calaway knew the industry was changing and made sure he wouldn’t be left behind. This style helped him transition beautifully into the Attitude Era and was further proof that 'Taker has always had one of the sharpest minds in the business.

12 Ministry of Darkness

via prowrestling.wikia.com

The Undertaker and Paul Bearer were back together and embracing a much more natural look, ditching the campy white face makeup.

Calaway was recovering from a hip replacement and employed a viscous stable of mini-groups like The Brood and The Acolytes to do his bidding, performing rituals and gang beating whomever they chose. The dark side of The Undertaker was far more embellished and over the top.

Although this gimmick lent itself perfectly to the over-the-top nature of this era, you might be surprised to learn it was Calaway's least favorite. Being a devout Christian, he wasn't particularly comfortable uttering Satanic phrases and performing dark rituals. Let's not forget he tied Stephanie McMahon to a friggin' cross! Taker though, being the selfless man he was, pushed through it and eventually reinvented himself altogether.

11 American Badass

via wwe.com

Calaway took eight months off to treat both a groin injury and a torn pectoral muscle, but all of that rehab was worth it for one of the greatest returns in WWE history.

It was an incredibly ballsy move to completely change such an established character, but it paid off and injected new life into his already long WWE career.

With the Rock outnumbered and beaten down in the ring, the crowd was eagerly awaiting a savior. They didn’t know what to expect with the new rock theme and silhouetted biker at the curtain, but once they figured it out they welcomed the former dead man back with everything they had.

The American Badass dropped cronies left and right on his way to the ring, laying an especially brutal boot to Shane before riding off on his Harley.

There are very few wrestlers that successfully changed their gimmick this drastically, and none got it over quicker than this.

10 Big Evil

via prowrestling.wikia.com

After a quick stint as a face, ’Taker returned to his evil roots, ‘Big Evil’ to be exact, when he forced Jim Ross to kiss Vince’s ass.

His hair was cut short and he started using more MMA-style submission moves.

He started a feud with Ric Flair, assaulted his son David and even threatened to hurt Flair’s daughter Charlotte! Perhaps we could see Charlotte get her revenge and challenge Undertaker for WrestleMania 33?

By mid 2002, Taker was back to being a face, as history has proven time and time again, no matter what Taker does, you can't boo him for long.

The Big Evil persona died at Survivor Series 2003, as The Undertaker lost a Buried Alive match to Vince McMahon (with Kane’s help).

But the Deadman would soon return.

9 WrestleMania XX - Deadman Walking

via wwe.com

An epic (even for him) entrance at WrestleMania XX brought The Deadman back to life for the WWE Universe. Paul Bearer’s face glowed creepily in the blacklights while hooded minions lit the ramp with fiery torches. The Undertaker strode menacingly down the ramp as an unmasked Kane could only exclaim “I buried you!”

This new hybrid style combined elements from various phases of his career. The Western Mortician styled black hat, leather trench coat, and MMA style ring wear completed the core look he would rock all the way to current day (with minor changes to hair and outfit).

The supernatural powers and invincibility returned as well, but at a lower intensity to suit a more realistic era.

The WWE would book him to return from destruction several more times in this period. Randy Orton, The Great Khaki, and Mark Henry all tried to end The Phenom, but couldn’t keep The Deadman down.

8 WrestleMania XXIV

via youtube.com

The feud between Edge and The Undertaker was considered by many the best of the year (in a year that also saw HBK vs Y2J and Angle vs AJ Styles).

Calaway’s best matches always seemed to happen with smaller opponents. Although incredibly agile for a large man, watching him slug it out with another giant rarely gets enough momentum going to be considered a great match.

Edge had the right mix of agility, brutality, and fearlessness that was required for battle with The Phenom.

For WrestleMania XXIV, Calaway kept the same core elements of his previous style but added a more elaborate leather robe that looked like it came straight out of his Ministry days. This would be the first time in 11 years 'Taker main evented a WrestleMania, having not done so since his victory over Sycho Sid at 13.

7 The Last Outlaw

via thearmbarexpress.com

Calaway and Triple H were referred to as the Last Outlaws, as they were the last two unretired wrestlers in the WWE from the New Generation Era (1993-1997).

For WrestleMania XXVIII, Calaway must have taken inspiration from the road warriors as he sported a short mohawk and a spiky leather jacket. He topped off the ensemble with a Ministry-esque hood that accentuated the reveal of his brutal new haircut.

This was a rough grudge match, featuring plenty of chair shots, an extended Hell's Gate, a chokeslam to a ref by the name of Shawn Michaels (that started a “this is awesome” chant) and even a sledgehammer to Triple H’s face.

After 31 minutes of battle, ‘Taker, Michaels, and Triple H left the ring together for their own version of the curtain call.

6 21-1

via thevoid.co.uk

This was tough to watch.

The Undertaker was starting to look old and struggled to lift the heavy Lesnar, audibly asking his opponent to help put his legs into position for the Tombstone.

After the shocking finish, Calaway struggled to exit the ring while suffering the effects of a concussion sustained earlier in the match. The crowd was stunned into silence and felt pity for the fallen hero, which is definitely not an emotion you want from a wrestling crowd.

The leadup to the match wasn't much better as both were working part-time, leaving most of the work to Paul Heyman. Even classic Heyman Hustle failed to properly elevate this bout.

When looking back, this feud will mostly be remembered for breaking the streak and making The Undertaker look more fragile than ever. It still remains to be seen if the choice to end the historic legacy was a wise one.

5 Old Man Instagram

via inquisitr.com

After finding out that Calaway suffered a concussion at the beginning of his WrestleMania 30 match, and was taken to a hospital after, we were then hit by this very unflattering photo.

Showing Calaway looking very gray, tired, and small, had many predicting we had already seen his last match.

The benefits of marrying a younger woman (who also happens to be a fitness freak), then came into play. Michelle McCool posted much better photos of our fallen hero, and he even became a bit of a social media sensation, at least in our pocket of the internet.

Seeing Calaway pumping heavy iron again and ready to kick some ass felt great and gave fans plenty to look forward to. It also told us we hadn't seen him for the last time.

4 Lesnar Rematch and Battleground

via fansided.com

Calaway proved the skeptics wrong and returned looking better than expected. The Battleground surprise was fun as hell (even if he struggled lining Lesnar up for the Tombstone).

The SummerSlam rematch had the raw energy and personal edge that a revenge bout needed. It was exactly what should have happened following the shock of breaking the streak.

The double sit-up and laugh was a bit goofy, but immediately punching each other while parked on their ass felt right, two titans wasting no time dishing out punishment.

You knew WWE was going to give ‘Taker the win, but giving Lesnar the Austin-esque refusal to submit, bleeding pass-out and defiant middle finger kept him looking strong. Not to mention, they did the screwy finish of Taker tapping but the ref not seeing it.

Eventually, Lesnar would win the rubber match at Hell in a Cell, providing a satisfying end to their feud.

3 Taker vs. Shane

via wwe.com

The hair was longer to match the old-school vibe of seeing Taker, Shane, and a Hell in the Cell, but the match and feud left a lot to be desired.

The storylines were all over the place. Shane had come back to an insanely positive reaction with promises to change the WWE for the better. Fans were ready for a fresh perspective and for a time, the shows actually seemed better.

To then pit The Undertaker against Shane made little sense and confused the fans. They didn’t want to boo either of them, both were old, and Shane was always limited in the ring.

The match and the feud were mediocre with the one highlight being Shane’s traditional suicide spot. He survived and the fans felt like they got their money’s worth, but overall, the entire thing felt unnecessary.

We’ve got at least one more Mania to send him out on a high note.

2 Crutches

via onbreaking.com

It’s becoming a tradition to worry about Calaway in between wrestling appearances, and seeing him on crutches took it to the next level.

We hadn't heard of any serious injuries or surgeries, but seeing an active member of the roster on crutches always sets off alarm bells.

On the bright side, other than the crutches he looked healthy and strong. Michelle McCool must be busting his ass in the gym to get ready for his next appearance. You’d have to think his next WrestleMania will be his last, but we’ve made that mistake several times before.

It would be nice to have one final run that ends with a better story than the slapped together Shane feud, but as long as he ends on his terms, I’ll be happy.

He would return sans crutches very soon.

1 Return to SmackDown 900

via wwe.com

Reports of his demise are always greatly exaggerated as The Undertaker returned to SmackDown Live looking just fine without his crutches.

'Taker came to deliver a warning to the SmackDown team ahead of their match at Survivor Series. Since his character carried SmackDown through the Ruthless Aggression Era, he felt like he had some authority on the matter. He didn't mention specifics, but he did tell the team that they should fear his wrath if they failed to make the RAW team rest in peace.

On the brighter side, he complimented Shane McMahon as the best candidate for SmackDown general manager, due to his lack of fear displayed at their recent WrestleMania match.

'Taker also addressed his tie to WrestleMania, proclaiming the event would no longer define him. This was a smart move considering the man who ended his streak would soon be squashed at Survivor Series a few days later.

Does that mean he should go after Goldberg next?

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