When The Undertaker was introduced in the WWE over 25 years ago, he was the embodiment of evil. A giant monster, infatuated with death (hell, he's from Death Valley), who put his defeated opponents in body bags and locked your childhood heroes in airtight coffins. He was the Big Bad that the good guys tried to Overcome The Odds™ and defeat.
However, in the pro wrestling world, nobody stays a bad guy forever and, eventually, Undertaker became so popular that a face turn was inevitable. Of course, then the next problem arose: when your ultimate monster bad guy is now a good guy, who does he fight? The answer to that, more often than not, was "someone dumb".
The past two and a half decades has seen Undertaker fight against some legendary opponents and not so legendary. There are also the occasions where his opponent is talented enough, but the pairing of the two simply makes no sense. Often since The Phenom would often be seen as a favorite, the WWE would find someone just as, if not bigger than 'Taker to make him seem like the underdog. The results were often terrible to say the least. It's no coincidence that The Undertaker's best matches came much later in his career, as the WWE finally started having him feud with the best talent, rather than the biggest guy they could find. Some of 'Taker's classics include his WrestleMania battles with Shawn Michaels, Triple H and some of his earlier bouts against technically sound guys like Bret Hart and Kurt Angle also were huge successes.
We decided to hop in the Wayback Machine and take a peek at the 15 worst pairings - be it as opponents or allies - that Undertaker has been stuck with.
Thankfully this was a disaster that we were all eventually spared. I'm cheating a little by putting this entry but the situation was such a disaster that it's worth mentioning.
Mordecai was promoted as a druid-like religious zealot who was the anti-Undertaker. He dressed all in white, said cryptic stuff and was just generally creepy. He was also terrible in the ring, something that didn't factor into the development of the character, apparently. So essentially the character they had created, primarily to feud with The Undertaker was so bad in the ring that their planned feud was nixed before it began.
Mordecai would get another chance at WWE success as Kevin Thorne in the company's relaunch of ECW and The Undertaker had one less stupid feud.
14 Nathan Jones
Nathan Jones had everything Vince McMahon allegedly looks for in a wrestler. He's big, he's got a great look , and he has a fascinating, real-life backstory. He was dubbed "The Colossus of Boggo Road", due to the time he spent in an Australian prison. After only a year, Jones - who, keep in mind, was an inmate in one of the most infamous prisons in Australia - left the company because travelling is hard.
Before he departed, however, he was booked as being mentored by Undertaker, who was in the midst of his Ooh Look At Me I Have A Motorcycle persona at the time. At WrestleMania XIX, he was supposed to be in a tag team match with Booger Red (Jim Ross really wanted people to call The Undertaker that) against A-Train and Big Show. He was so bad, he was actually taken out of the match and Undertaker just did it himself.
13 Damien Demento
Mr. Demento here has the distinction of wrestling against Undertaker on the very first episode of Monday Night Raw. Undertaker is the only wrestler to appear on that episode that is currently an active member of the WWE roster. Depending on how you define the word "active", anyway.
Thankfully, we weren't subjected to very much more of either this pairing or Demento himself.
12 Kama Mustafa
As I mentioned in the introduction, not everyone on this list is a terrible wrestler. Charles Wright, the man who would eventually go on to find his greatest success as The Godfather, was not a terrible wrestler. He was actually a pretty good one. He was also repackaged more times than the Beatles catalog.
He originally began in WWE as Papa Shango, a voodoo witch doctor that inexplicably did not feud with Undertaker. He would later become Kama, The Supreme Fighting Machine (the "Mustafa" would be added later), who pretended to be a UFC-style shoot fighter because WWE hadn't bothered to hire Ken Shamrock yet. Kama would steal Undertaker's urn and melt it down, turning it into a gold chain. The fiend! Anyway, this went nowhere and Wright eventually joined the Nation of Domination and then became a pimp. You know, like ya do.
11 The Big Boss Man
The Hell In A Cell match is as much a part of Undertaker's mythos as anything else. His "brother", Kane, debuted during one of these matches. He threw Mick Foley off the top of the cage during another. Sadly, he also fought Big Boss Man in what is probably only the second worst match involving this particular cage (the first, of course, being Boss Man's Kennel From Hell match with Al Snow).
The Undertaker and his aforementioned Ministry were feuding with the McMahon family's Corporation back in 1999. Boss Man represented said Corporation in a match with Undertaker at WrestleMania XV because of course it was at WrestleMania. The match ended with Undertaker literally hanging Boss Man from the top of the case as it rose up and away from the ring.
10 Diamond Dallas Page
What's really depressing about this entry is that this feud could have been awesome. Shortly after WWE's purchase of WCW - and shortly before the "Invasion" angle - handheld camera footage began airing that creepily followed around Undertaker's then-wife, Sara. This would go on for weeks, until the stalker was revealed to be DDP himself. What should have followed was an intense, kick-ass feud between two of the toughest guys in the wrestling business.
Instead, Undertaker brutally dominated Page in every match they had. Brutally. In a number of matches, Page got virtually zero offense in. Sara even pinned Page at one point. What could have been a feud similar to Page and Randy Savage's WCW feud a few years earlier instead turned into a farce that just seemed like a way to make a former WCW guy look really, really bad.
Out of all of these feuds, this was the only one to feature an actual WrestleMania main event. And, on paper, you would think this would be a pretty good match-up. Two distinctive big guys with proven experience. Both were world champions previously - and Sid was in the main event of WrestleMania previously (WrestleMania VIII). What should have been Undertaker's finest moment to date (and, to be honest, kinda was in a way), was marred by a number of factors, most of which were out of the control of the participants. We're putting it on this list anyway.
For starters, it had the unfortunate distinction of being the main event of one of the worst WrestleManias from both a critical and financial standpoint (it's the only 'Mania, so far, to have never sold out). Their match also went on two spots after the classic Bret Hart/Steve Austin submission match - a daunting challenge for a match on any card, much less one as tepid as this. Factor in a bunch of interference from Bret Hart, the already dismal state WWE was in at the time and the fact that Sid probably would have rather been playing softball at the time, and you have one of Undertaker's more unfortunate match-ups.
8 King Mabel
The two did battle at the 1995 King of the Ring, where WWE inexplicably had 'Taker job to Mabel in the quarterfinals. Mabel wound up winning King of the Ring, but not before having broken 'Taker's orbital bone in a match.
Because he was seven feet tall and weighed about 900,000 lbs. (approximately), he was supposed to be thrust into a feud with Undertaker. After nearly crippling Kevin Nash at SummerSlam, however, most of WWE's big plans for Mabel were dropped and he was eventually released from the company. He would also form a team at Survivor Series that year to take on a team Undertaker assembled.
Heidenreich was a poetry spewing maniac who raped Michael Cole on television while reading him poetry (I mean, he didn't really rape him, although he did really read him poetry). For some reason, he feuded with Undertaker, a feud that ultimately led to a casket match of all things at the Royal Rumble in 2005. He and fellow lunatic Snitsky were supposed to have a tag match against Kane and Undertaker, but Undertaker basically said "HAHAHAHAHAHAHAHAHAHA no."
6 The Great Khali
It hasn't been that long since Khali was last seen in WWE, so he should still be fresh in the minds of a lot of you. While he was last seen as the "Punjabi Playboy" - a fun-loving, dancing (I'm assuming that was dancing, anyway) good guy - he was introduced as a giant monster who decided to attack Undertaker from out of nowhere because, sure, why not? As we'll see soon, that's not exactly a recipe for success.
He also walks as if nobody had bothered to tell him what his knees actually do.
5 Muhammed Hassan
I could write an entire article on its own on why the Muhammed Hassan character failed. But since we don't have that much space right now, here's the gist. Hassan - played by Mark Copani - was an Arab-American who was using his role as a WWE Superstar to protest the way his people were treated in the U.S. following 9/11. It was actually kind of brilliant and Copani was a really good wrestler (he's retired now). In fact, the reason he's on this list isn't even his fault.
In 2005, during an episode of Smackdown! (which was on network TV at the time), his manager Daivari was in a match with Undertaker. During the match, Hassan started "praying", which apparently caused five men in ski masks to rush to the ring and attack Undertaker. Oh, this pre-taped segment also happened to air on the same day as the 2005 bus bombings in London. After that, UPN no longer wanted Hassan on their network, and Hassan was eventually sent back to developmental and then released.
4 Vladimir Kozlov
Vladimir Kozlov was a badass Russian who was played up like an old school Soviet fighting machine - like Rocky IV's Ivan Drago, but for a new generation. That was the problem. There was a whole generation of fans who weren't even born when the USSR collapsed, much less were alive when Rocky IV was released. He also wasn't all that interesting, or fun to watch in the ring, or had much charisma or, well, you get it.
But, whatever. He had a feud with The Undertaker and it was dumb. And, like most monster heels that get fed to the Undertaker, he eventually became a comedy face and drifted off to parts unknown.
3 Mr. Kennedy
Ken Anderson was a legendary quarterback for the Cincinnati Bengals who, in 1981, won the NFL's awards for both Offensive Player of the Year and Comeback Player of the Year. He holds team records in categories such as career wins, games played, touchdown passes and more. He also has a Super Bowl ring from his time as a coach for the Pittsburgh Steelers. He's awesome.
There's also another Ken Anderson who, for a time, went by the name "Mr. Kennedy" in the WWE. When he wasn't busy getting injured himself, he was injuring people he worked with. He feuded with the Undertaker and it was dumb and let us never speak of him again.
2 Hulk Hogan - 2002
In all honesty, the two major programs that Undertaker worked with Hulk Hogan were actually really good. The first was at the end of 1991, in which Undertaker beat Hogan for the WWE Championship at Survivor Series (with some help from Ric Flair, who had just joined the company). This led to a series of events that would eventually culminate with Flair winning the title in what was, arguably, the greatest Royal Rumble match of all time in 1992.
In 2002, Undertaker defeated Hogan for the WWE Championship once again, ending Hogan's feel-good nostalgic run with the title. However feuding with an aging Hulk Hogan also made for a painful pace in their match at Judgment Day 2002. Just look at the chokeslam 'Taker tries to deliver on Hogan.
1 Giant Gonzales
Well, it's all come down to this. The worst feud Undertaker has ever been stuck with. Let's do this.
Jorge Gonzales - who, as far as I know, was a nice and decent man who just wanted to entertain people - began his wrestling career in WCW as El Gigante. The nearly eight foot tall Gonzales was originally drafted by the NBA's Atlanta Hawks, but when his career came to and end due to his bad knees (a nearly eight foot tall wrestler with bad knees?! Say it ain't so!), Hawks owner Ted Turner offered him a job in WCW. It was fine. He fought Ric Flair and went on a date with Missy Hyatt, two things I've never done, so who am I to judge?
Eventually he made his way to WWE, where he was managed by Harvey Whippleman of all people and thrust into a feud with the Undertaker. Not realizing what WCW did (how often do you hear that?) - that Gonzales was a fun side character but didn't really have any wrestling skill - Giant Gonzales faced Undertaker in a marquee match at WrestleMania VII in which Undertaker won because Gonzales was disqualified for using chloroform to knock him out.
When I say that Giant Gonzales makes the Great Khali look like Lou Thez, you can see why I put him at #1.