The Undertaker’s legacy speaks for itself. He’s wrestle many of the greats: "The Immortal" Hulk Hogan, "The Game" Triple H, and "The Heartbreak" Kid Shawn Michaels to name but a few. His matches at any WrestleMania will go down in WWE history, from the beginning of The Streak until its shocking end at the hands of Brock Lesnar at WrestleMania XXX. But The Undertaker has had some poor opponents over the years as well. So here is my list of 15 of the worst wrestlers The Undertaker has had to work with. You may recall some of these while you may have blocked some from your memory because they were that bad.
16 Fake Undertaker
Brian Lee AKA The Fake Undertaker AKA Chainz from The Disciples of Apocalypse. Lee was actually the real life cousin of The Undertaker. To be honest Brian Lee could wrestle but for some strange reason the match at SummerSlam '94 went down in regards to how poorly the match structure was. It began when "The Million Dollar Man" Ted DiBiase tried to buy The Undertaker and make him part of his stable, The Million Dollar Corporation which included stars such as Tatanka, Bam Bam Bigelow, 1-2-3 Kid, Karma, Nikoli Volkoff, King Kong Bundy and the taxman Irwin R Schyster. With The Undertaker refusing to join, DiBiase told the world that he owned the real Undertaker and that fans would see him go on one on one with Paul Bearer's Undertaker at SummerSlam '94. The match wasn’t very good at all and fortunately that was the only time we saw the fake Undertaker.
15 Giant Gonzalez
The Giant Gonzalez was originally from Argentina and many fans may know him as El Gigante from World Championship Wrestling. Now, standing over seven feet tall you would have to know that there are definitely some limitations in regards to working in a wrestling ring. This proved to be the case at WrestleMania IX. Accompanied by his manager Harvey Whippleman, Giant Gonzalez made his debut against The Undertaker. Caesars Palace, Las Vegas, Nevada was the setting as the two biggest men in the WWE went to war. The match didn’t last very long and during the closing moments Gonzalez produced a hand towel coated in ‘chloroform’ which finally put The Undertaker ‘down.’ However minutes later The Undertaker would reappear and take out the Giant as the "Macho Man" Randy Savage said ‘you can’t kill a dead man.’ Poor match in ring but the story told was great. Gonzalez didn’t last much longer in the WWE and was released later.
14 The Great Khali
During an episode of WWE SmackDown, The Undertaker was in the middle of a match with "The World'S Strongest Man" Mark Henry when The Great Khali made his long awaited debut with his main target being The Undertaker. The two went at it and Khali showed his dominance. We all know that once again if you’re too big then the matches aren’t going to be classics. The feud between the pair went on for months and accumulated in the first Punjabi Prison match. However, The Great Khali got injured before the match and was replaced by Big Show. The structure was amazing, however, the match was less than a classic with missed timed spots, poor selling, and a poor finish. The fans really wanted to see another good big man but were unfortunately let down.
13 Sycho Sid
The Undertaker battled Sycho Sid Vicious at WrestleMania 13. Sid defended the WWE Championship against The Undertaker. Bret "Hitman" Hart interfered during the match and gave The Undertaker the opportunity to hit the Tombstone Piledriver, cover Sid for the pin, and became a two-time WWE Champion in the process. The match itself wasn’t amazing in all honesty. It was back and forth for most of the match as you would expect from this kind of match. As always The Undertaker made Sid look like a credible champion. These two did clash after but Sid left months after to re-join World Championship Wrestling. The Undertaker would go on as champion until finally losing the title months later. The problem they had was having two big guys tell a "believable" story. Only when The Hitman became involved did the story make sense. Unfortunately this happens a lot in WWE.
12 Shane McMahon
Now I popped when Shane McMahon returned this year on Raw during a segment with Vince McMahon and Stephanie McMahon. And it was great that he was back in the WWE, but why put him in a WrestleMania match with The Undertaker? It made no sense whatsoever. That and the fact Shane hadn’t wrestled in years put the match in doubt from the first announcement. The WWE put two faces in a match which ultimately everyone wants to see The Undertaker win. The match was shambles, the selling was poor, nothing made sense ,and I’m guessing the fans felt bad for these two as both have given their bodies to the business over the years. The match was full of unnecessary bumps, just so WWE could give The Undertaker a match at WrestleMania. There was no return match or feud after this encounter, so my question is why have that match In the first place?
11 King Kong Bundy
Now we all know as wrestling fans the boundaries and limitations associated with King Kong Bundy and his wrestling ability. Putting a guy like this against "The Phenom" probably wasn’t the best booking WWE did. At WrestleMania XI The Undertaker battled King Kong Bundy, which in theory was the one of the real big men of the old school era that The Undertaker battled against. As predicted the whole match made no sense whatsoever and only a victory for The Undertaker helped by continuing with The Streak. The thing was at the time King Kong Bundy was at part of The Million Dollar Corporation and if the WWE had written it properly that could have been the end of The Streak there and then, based on the amount of guys that Ted DiBiase had. Fortunately the rematch never took place and the WWE fans I think we’re happy about that.
"Big Daddy Cool." The seven foot tall Diesel had been an opponent a few times for The Undertaker over the years but can we really say we’ve actually enjoyed any of the matches we’ve seen apart from when The Undertaker beating Diesel at WrestleMania XI to continue The Streak? At this point, fans and the WWE were starting to pay attention to The Streak. The point I’m making is that any big guy that battles The Undertaker and is taller than The Undertaker always seems to be sloppy in the ring when one-on-one with "The Deadman." The thing is, you can’t go into any technical wrestling because story wise it just wouldn’t make sense. That’s why most of these big man matches are always brawls, Because it makes sense. Everyone loves a big guy brawl, however, there is only so much one can do in those kind of matches and it shows.
8 Big Boss Man
The Big Boss Man was a different kind of big man as he could move in the ring well. However, he was very limited in regards of his move set. This feud went on maybe longer than it should have after The Corporate Ministry dissolved. The feud lasted months and resulted in a Hell in a Cell match at WrestleMania XV. This was unlike anything we’d seen before. After the match was won, Edge, Christian, and Gangrel approached the cage and brought with them a noose. Yes, a noose to publicly hang Big Boss Man live on WWE PPV. This obviously wouldn’t have gone down well with today’s fans. The feud ended WITH Boss Man returning months later to do battle with The British Bulldog over the Hardcore Championship. With the ability of The Undertaker it’s harder to do those kind of matches with bigger guys, mainly because everything needs to look real in theory.
7 The Executioner
This was one of most mismatch opponents that The Undertaker ever faced. To many fans The Executioner was basically a jobber, but because of his size he would last a bit longer in matches than many other jobbers during the mid '90s in WWE. The original feud was The Undertaker and Mankind. However, for some reason Creative threw in The Executioner to lessen the odds of The Undertaker’s chances of winning at In Your House: Its Time. This match was billed as an Armageddon Rules match, which were never explained properly as it showed at the end of the match. The Undertaker beat up Mankind and left him in the crowd. The Executioner was left all alone and took a Tombstone Piledriver. The Undertaker covered him for the three count, the bell never rang, and the referee then counted to 10 as in a Last Man Standing match. So no one really understood the concept of the match.
6 Dwayne Gill (Later Gillberg)
This match took place in September '91 on WWE Superstars of Wrestling. Following his unstoppable force in matches, The Undertaker didn’t hold back and beat up Dwayne Gill. The problem was Gill's bumping. With The Undertaker doing his trademark moves, all Gill did was dead sell which for me wasn’t good enough to put The Deadman over. The problem with this match in general was even though it was a squash match (this means the main wrestler winning in minutes maybe seconds), WWE later on used Duane Gill as Gillberg to mock at the time current World Championship Wrestling Heavyweight Champion Goldberg. This match or these kind of matches never worked for me as it was always a mismatch in regards to talent. That and the fact Duane Gill was half the size of The Undertaker. So fans knew instantly that he was going to get beat. The only thing the fans didn't was how long it would take.
After an altercation at Survivor Series, Mabel went on to defeat The Undertaker in the finals of the King of the Ring '95 tournament. That’s where we got King Mabel and Sir Mo. Now fast forward a few months to In Your House: Season Beatings where the two squared off in the infamous Casket match. The match itself wasn’t fantastic and so things didn’t make sense in regards to the actual size of King Mabel (let’s remember King Mabel was over 500lbs). The match went straight into a brawl. The end of the match wasn’t bad as The Undertaker retrieved the urn back from around Sir Mo’s neck as previously Men on a Mission had melted the urn in a huge gold chain. Sir Mo wore this around his neck during matches at ringside. In the end, The Undertaker closed the lid of the casket to win the match.
4 Vladimir Kozlov
At the time, the Russian, Vladimir Kozlov was undefeated in WWE when he stepped into the ring with The Undertaker live on SmackDown. At this point Kozlov was thought by many to be the next big heel. This match was just before WrestleMania and surprisingly Kozlov went over and secured the pin on The Deadman after reversing Old School into a Powerslam. Kozlov then went on to wrestle Shawn Michaels the following week on Raw and lost. The thing was The Undertaker made the match on SmackDown look amazing and put the Russian over but nother really came of that. That was the end of this very short feud as Shawn Michaels went on to wrestle The Undertaker at WrestleMania and subsequently lost, allowing The Undertaker to continue The Streak. This could have been a good feud but Kozlov was far too green to be put in a long term program with The
"The Ugandan Giant." The guy who scared grown men and terrorized Memphis Wrestling back in the '80s. WWE snapped this guy up and Kamala was a big time heel in the company, alongside his handler Kimchee and his manager Harvey Whippleman. The Uganda Giant wreaked havoc on the WWE roster. As the WWE were heading for Survivor Series 1992, Creative came up with having Kamala face The Undertaker in a Coffin match, later known as a Casket match. The Undertaker sent The Ugandan Giant away until Kamala turned face and disposed of Kimchee and Harvey Whippleman. Now this gimmick match would have worked better if the match was good. WWE fans saw this as an average match but the concept was great, giving The Undertaker his own gimmick match. After Kamala turned face these two never got in the same ring together which was probably for the best.
2 Orlando Jordan
This match was on SmackDown and was originally set to take place against John "Bradshaw" Layfield. However, JBL faked an injury and decided to put his Chief of staff Orlando Jordan in as his replacement. The WWE Championship was on the line as well after Teddy Long demanded this match to happen. During this match there were some mistimed and sloppy spots which made this match bad. Outside interference from JBL cost The Undertaker the match. The best part of this was when The Undertaker removed the protective neck brace of JBL and hit him with a Chokeslam. The crowd went nuts for this but after a shocking match the crowd went home happy. During this feud The Undertaker actually sacrificed Orlando Jordan live on an episode of WWE SmackDown to make a statement. The role Orlando played in this feud was great but his in ring ability didn’t live up to the same amount.
At the Royal Rumble, The Undertaker and Heidenreich settled a feud with a good old Casket match. But not before a lovely poem from Heidenreich prior to the match in a video promo. The actual match at the Royal Rumble was very poor and once again The Undertaker had to bring out a good match from the big man. It was just sloppy from start to finish. Even a Single Leg Boston Crab in the early stages of the match made no sense. Then Heidenreich tried to grab the rope nearest to the Casket. The fact that Heidenreich even went for the pin showed that he was unaware of the stipulations in regards to the Casket match. Following a Chokeslam and a Tombstone Piledriver, The Undertaker was victorious.
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