Top 10 Worst Undertaker Matches

WCW had him first as Mean Mark but didn't know what to do with a guy who 'never smiled'. The WWE proved yet again why they were superior and created an icon.

Mark Calaway has become as mythical as his character. His annual appearance at WrestleMania is a must-see for wrestling fans and his streak had crossed over to the mainstream (well there goes that). A physically intimidating monster who launches his body through the air and walks the top rope, Calaway has had many classic matches and moments. He remains the only person to defeat Hogan for the WWE title twice.

But of course they can't all be five stars. Since Calaway was one of the few WWE stars to never cross over to the WCW it means he was at the top of the extremely thin roster during 94-95. He was reduced to main eventing PPVs with Mabel, Yokozuna, and even himself!

His style is utterly captivating when he plays the monster but can be extremely plodding when facing equally large opponents. Most big men cannot move the way he can and it sends the match into slow-motion. His bouts with Giant Gonzales are akin to watching whales battle underwater.

The Undertaker was constantly saddled with limited, clumsy big men early in his career. Once he got some real opponents like Mankind, Bret Hart and Shawn Michaels he began churning out some classics. He's also one of the few wrestlers that most of his best matches took place in his 40s, with the likes of Kurt Angle, Shawn Michaels, Edge and Triple H.

I didn't include Lesnar breaking the Streak as it still feels too soon to fully appreciate the impact. Such an incredible record that couldn't possibly be duplicated better have a damn good reason to stop. It would have been so easy to let him retire with it intact and instead the honor was given to a man who could have easily left the company forever and instead chose to come back part-time.

I've also excluded non-PPV matches. Mediocre Raw/Smackdown and/or squash matches exist but it's all about expectation. If he takes on Damien Demento you aren't expecting much, but if people have shelled out significant cash for a PPV it better be worth their while.

So let's take a trip down to Death Valley and check out the lesser-lights of a historic career.

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11 Kane, Judgment Day 1998: Austin rules, this match did not

Not a terrible match wrestling-wise, but an over-bookeded ending made zero sense and lost the crowd. Typical of WWE at the time; screw everyone else and focus on Austin.

It made sense to some degree as Austin did get the biggest cheer as the guest referee and provided some great entertainment early on with his biased counting. But once Austin was accidentally struck by an irish-whipped Undertaker, it all went to hell.

Kane immediately forgot about winning and chokeslammed Austin (although he had been favoring him the entire match). The brothers nonsensically teamed up to beat Austin down for a few minutes before Undertaker turned on Kane again.

Hey, let's throw Paul Bearer into the mix! He appeared to offer assistance to Kane but of course turned on him. Russo swerve! Undertaker nailed Kane with the chair and then went for the pin and expecting Austin to count, like this is just a regular old match.

Oh yeah, then Austin stunned Undertaker (which he no-sells) gives him yet another chair shot and counts them both 1-2-3 to declare himself the winner.

Highlight of the night is seeing Vince get hit with some debris from a fan.

10 Big Show - Punjabi Prison Match, Great American Bash 2006

via wwezone.org

Pronounced 'poonjab' by The Undertaker.

If you're going to use the WCW's PPV name you might as well go full-WCW and include an overly-complicated gimmick match.

A last-minute backstage segment revealed that Big Show would replace The Great Khali in this one (if you could hear anything with Khali yelling incoherently). Big Show was upset enough at the decision that he was crying during both entrances. Weird start.

I don't understand what he was so upset about. He had already been in a Buried Alive Match in '99. Surely the prospect of DEATH is much worse than a simple wooden cage match. You'd think someone who resembles a giant panda would be happy to see so much bamboo.

Kudos to The Undertaker for once again surprising everyone with his agility. He performed some great maneuvers off of the cage, swinging from a rope and even performing a splash to break through the prison. But a few interesting spots couldn't save it.

It ends with The Big Show on his knees crying (probably because he wasn't allowed to eat any of the bamboo)

9 Jimmy Snuka, WrestleMania VII

A match far more important than entertaining. The Undertaker had already won over the crowd by this point and received an impressive cheer (not common for heels of the time) as his bell tolled.

Snuka was in the ring first with little fan-fare and you could see his WWE career about to be buried by the 'Taker. He would be out of the company soon after.

Basically an impressive squash with the winner taking the nickname "Phenom".

8 Old Kong Bundy - WrestleMania XI

via pwmania.com

The Undertaker sure was a good sport. He was stuck with a seemingly endless line of lackluster feuds throughout the New Generation Era. His irritating run against the Million Dollar Stable saw a rotating group of mediocre heels obsessed with stealing his urn. IRS (the best of the bunch), pre-Godfather Kama, and even the over-the-hill King Kong Bundy were all involved in forgettable matches that always ended with the next henchman stealing the Urn.

Bundy was simply too old, slow, and heavy for this to be any kind of a match. It's probably the only time 'Taker couldn't Tombstone his opponent and had to settle for a TombSlam instead.

7 Dudley Boyz, Great American Bash 2004

This was an awful main event to an awful PPV. The Dudley Boyz on last? What is this, an episode of Smackdown?

The match failed to get into any kind of rhythm and Paul Heyman's distracting in-match promos disrupted the flow of the action.

The only thing more ridiculous than thinking this would be a proper main event was the finish. I wasn't aware The Undertaker could launch lightning bolts (from inside a building no less) but that's what he did to prevent Heyman from burying Bearer in concrete. But after producing said lightning bolt and battling two men to save a life, The Undertaker randomly decided to kill Bearer anyway.

Just another casual murder to end a PPV. They should have killed this match before it ever happened.


5 Giant Gonzales - WrestleMania IX

via wwe.com

The best part of this one was Undertaker's chariot entrance with the vulture, after that it was all downhill.

Can't blame the 'Taker on this one as Giant Gonzales has always been extremely limited in the ring. Letting him use chloroform is genius in hindsight as it doubled his move-set. Perhaps it was a metaphor for the match, as it felt like we the fans had been given a severe dose of chloroform as well.

Having the all-star broadcast team of Jim Ross, Bobby Heenan, and Savage ("chloro...foam") certainly helps. If you enjoy awful/goofy matches there's some entertainment to be had.

At least it gave Gonzales his WrestleMania moment and another notch for the streak.

4 Mabel - King of the Crap '95

One of the reasons this card sucked was that the WWE kept its precious few stars out of the tournament finals. Undertaker and Shawn Michaels out in the first round, and Mabel and Savio Vega in the finals. That'd be like needing Michael Jordan to make a winning basket in a playoff game, but you bench him and put the ball in Joe Kleine's hands instead.

This match was 10 minutes of Undertaker getting in his classic moves and Mabel performing a horrifically confusing forward slam-type thing. Obviously Mabel didn't win clean, but the interference was weak; Kama the Fighting Machine ran down and delivered a Daniel Bryan kick to COMPLETELY INCAPACITATE 'Taker, causing him to get pinned.

Easter Egg for the fans, check out the young Hardy Boys guarding the aisle door (get that gum out of your mouth Jeff!)

3 Big Boss Man - Hung in a Cell

via sportskeeda.com

This one was so bad they didn't even bother including it on the HITC DVD. Ray Traylor had always been a serviceable mid-carder but his pairing with The Undertaker in such a high-profile bout was going to be an up-hill battle.

The crowd wasn't into it and it was over in less than 10 minutes. Of course then we had to wait another 10 minutes for all of the Ministry to safely descend and perform the ridiculous hanging gimmick.

Fans will suspend disbelief to enormous lengths (this is pro wrestling after all) but the WWE has to put a little more effort into it. It was done with all of the drama of lifting a piano. They HANGED A MAN TO DEATH and then immediately talked about the next order of business like nothing happened.

It went down in history for all the wrong reasons.

2 Undertaker vs. Undertaker

You can't fully appreciate great acting until you've seen it done poorly and that's how I felt watching this match. The only positive from watching someone imitate The Undertaker is the new found respect you get for the real deal. It's a lot more than just stiff movements and throat strikes. It proves the only man that could truly pull off a gimmick as sensational as The Undertaker could only be Mark Calaway.

It really wasn't fair to Brian Lee in the first place. He had zero main event experience in the WWE and was limited to copying 'Taker's moves.

Having an entertaining match with two Undertakers was always going to be near impossible. The Undertaker's style obviously works better against a smaller, faster, and 'human' opponent. The crowd really had no idea what to make of the match and was awkwardly quiet ("in awe" as Vince says). Even the commentators were at a loss for words.

The buildup to this was botched and they announced the match before they had even progressed the storyline to reveal there were two of them.

The WWE showed how well they learn lessons by running the exact same story with impostor Kane.

1 The Brothers of Destruction vs. The Brothers of Botch

KroniK comes down to the ring somehow looking even MORE like strippers than when they were in WCW.

Having four big men in this tag match meant they had plenty of energy in between them to botch an impressive amount of moves. After Undertaker missed a knee by a country mile Jim Ross kindly put the focus on the punch he actually connected with (what a pro). But Adams outshined everyone with the weakest attempt at running into a ring post you'll ever see.

Did these guys all get wasted together the night before? The other matches on this list were merely boring, but this was a colossal botch-fest and the embarrassed look on 'Taker's face said it all.

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