Glenn Jacobs is nothing if not a living wrestling legend. We’ve known Jacobs for nearly twenty years as “The Big Red Machine” Kane, though that’s not the only name he has wrestled under. He was involved in the professional wrestling business for years before the monster we know now first made his way down to the ring and ripped the door off of the Hell in a Cell structure to reach his estranged brother, the Undertaker.

During his first year behind the mask, Kane would go on to play a starring role in the most immaculately constructed storyline the professional wrestling industry has ever seen when he chased his older brother all the way to a showdown at WrestleMania. His career went on to see many more moments worthy of an induction into the WWE Hall of Fame, including several runs with the WWE World Championship and performances that made Kane one of WWE’s most decorated tag team performers.

Since his debut, Kane has undergone a wide variety of character transformations, but despite his myriad of legendary accomplishments, many of his biggest moments were memorable for all the wrong reasons. Certainly, Kane is one of Vince McMahon’s most loyal and longest tenured employees, and there is a lot to revere the man for, but the versatile range of skills possessed by Glenn Jacobs as a performer have seen to it that he’s been used by WWE on every end of the entertainment spectrum and much of it has been rather embarrassing. Let’s take a look at some of those moments Kane would probably prefer we all forget ever happened.

15. Mike Unabomb

At nearly seven feet tall and tipping the scales at well over three hundred pounds, the frame of one Glenn Jacobs was a natural fit to play an apparently invincible Michael Myers-esque psychopath hell bent on complete destruction. As it happens, the full faced mask Kane wore in his early years tended to hide the fact that Jacobs is actually quite expressive and the murderous villain thing is something he can naturally pull off with ease.

That was the case in the early 1990s when Jacobs was wrestling under the ring name Mike Unabomb. Like Kane, Unabomb was similarly sadistic but didn’t see a whole lot of success. Along with his tag team partner at the time, Al Snow, Unabomb did capture the Smoky Mountain Wrestling Tag Team Championship, but the character soon faded into nonexistence and is not likely to be seen high on the list of career bullet points for Glenn Jacobs.

14. Anger Management

The character of Kane has always been one that WWE has managed to repeatedly reinvent to keep fresh for the audience and Glenn Jacobs has always been versatile enough to make just about anything work to its best potential. When Kane was paired with the mega-popular Daniel Bryan and the two were called Team Hell No, it was an easy win for the company because the fans took instantly to the tag team. Kane and Bryan showed remarkable chemistry and their varying in ring styles complemented one another greatly.

During their run as WWE World Tag Team Champions, Team Hell No was on top of the tag division with few teams in sight who could compete with their popularity. But it wasn’t all wine and roses; one of the team’s storylines saw Kane and Daniel Bryan enter anger management to help with their constant bickering. When we saw the Big Red Machine wearing a graduation gown after completing anger management, we all knew this had gone too far.

13. First Championship Reign

As we are all well aware today, Kane has at times been one of the most dominant men in the entirety of WWE. He is one of the company’s most decorated athletes of all time and has won more Tag Team Championships than we can count with as many different tag team partners. But as all wrestling fans know, every professional wrestler aspires to achieve the ultimate goal of one day becoming a World Champion for WWE.

Kane has done just that on more than one occasion. In fact, he had a particularly lengthy and memorable run a few years back as the World Heavyweight Champion on SmackDown, during which he once again revived his on again, off again rivalry with his older half-brother, the Undertaker. That title reign may have been impressive, but his first taste of World Championship gold in WWE came when he won the WWE Championship in 1998 only to lose the title twenty-four embarrassing hours later.

12. Working Concessions

Kane is known throughout the wrestling world as one of the most sadistic and imposing figures to ever step foot inside the ring. So much of his mystique over the years has depended on his intimidation factor. He was completely unapproachable; if someone caught the monster in a foul mood, he would Chokeslam them through a table or perhaps even light them on fire. But in 2014 WWE seemed to toss all of that out the window with Concessions Kane.

Concessions Kane was the result of Triple H and Stephanie McMahon, or The Authority, losing their storyline jobs and Kane, who worked for the Authority as Corporate Kane (more on that later), being forced to look elsewhere for employment. The man who once struck fear in the hearts of children and grown men alike was now serving them all hot dogs and taking orders from his new boss, a tiny but fiery young woman.

11. Setting Jim Ross on Fire

No one in professional wrestling will ever be more closely aligned with the element of fire as the Big Red Machine himself. Kane’s entire origin storyline revolved around him being the survivor of a devastating fire set by his brother the Undertaker, and throughout Kane’s illustrious career fire has continuously made recurring appearances in various forms. For instance, Kane was the reason for the birth of the Inferno match and has played with fire more than once during his matches.

One would think that having set someone on fire could only enhance the creepy nature of a character like Kane, but the circumstances surrounding his burning of “Good Ole” Jim Ross were just too silly to have any serious effect. Kane had recently unmasked and completely snapped on WWE television, but attacking and setting ablaze an overweight and helpless, though beloved, commentator was not the best way to exhibit total dominance over a roster full of buffed up professional athletes.

10. Kane-anites

Being the notoriously intimidating monster he is, Kane has always had some problems with WWE watering down his character with comedy and light-hearted moments. The company has often attempted to offset these moments with the darker themes of ruthlessness and fire, but all it takes is one silly little line of dialogue to do irreparable damage to the image of a man who is supposed to strike fear into all of us.

That’s exactly what happened one fateful night in the early 2000s during a backstage scene between Dwayne “The Rock” Johnson, Hulk Hogan, and the Big Red Machine himself. Following a discussion between Hogan and The Rock, who were to be teaming with Kane later in the night, the masked freak who then shouted catchphrases and proceeded to lovingly refer to his adoring fans as his “Kane-anites.”

It was a hilarious moment, but also one that showed just how far he came from the hulking superstar he once was.

9. Shane McMahon’s Testicles

Soon after unmasking in 2003, Kane completely lost it and started destroying everyone in his path. One night he crossed paths with Linda McMahon, at that time the CEO of the company, and decided to drop her with a Tombstone Piledriver on the steel flooring of the entrance stage on Monday Night Raw. This spurred a violent response from Linda’s son Shane, who embarked upon a lengthy rivalry with Kane from which fans are still recovering.

Not only was the feud overly long and boring, but the most memorable moment from the entire ordeal was when Kane attached a battery to Shane’s testicles and electrocuted him. Here was a man WWE was positioning as a sick and unstoppable beast, but he seemed to have the sense of humor of a high school teenager. If they were going for disturbing, they missed the mark by quite a lot on this one.

8. Corporate Kane

Kane is unstoppable. That is what we’re supposed to believe, anyway, if WWE’s storylines are anything to judge by. Unfortunately, the company has seen to it that every bit of mystique has slowly been drained from the character over the past two decades through comedy routines and the like. However, just when it appeared the Big Red Machine could not be watered down any further, a few years ago WWE decided to scrape the bottom of the barrel.

We spoke earlier of Concessions Kane and how a monster serving hot dogs isn’t really a monster at all, but Concessions Kane could not have existed if it were not for Corporate Kane. When The Authority found itself in need of a defense mechanism, Kane was hired as the Director of Operations and he handed over his mask to Stephanie McMahon. Fans just cannot unsee Kane in a suit and tie, and he will never be able to believably pull off the monster thing again.

7. John Cena Feud

It was a widespread prediction among wrestling critics that the unmasking of Kane would also be the undoing of Kane’s entire career. However, he surprisingly went on to many years of success after he removed the mask and even finally enjoyed the extensive run with the WWE World Championship which had always eluded him. He may have been a stronger character before, but without the mask Kane arguably saw greater successes added to his resume.

But when all that had run its course it was time for the famous mask to make a return, and that it did. In what was supposed to be a triumphant rebirth of the demonic Kane character, the Big Red Monster debuted a new mask and entered into a rivalry with the one and only John Cena. Unfortunately for both of them, this feud was rated by many as the worst of the year and fans could not wait for it to be behind them.

6. Unmasking

It’s one of the most talked about topics of Kane’s entire career and also perhaps the most divisive and controversial, but whether present or not the mask will always be Kane’s defining feature. It is an integral piece of the puzzle that is the Big Red Machine and was his most terrifying feature in his early years, perhaps even scarier than the actual physical manifestations of his rage and remorselessness. That mask made Kane the World Wrestling Federation’s resident equivalent of the bad guy in a Hollywood horror film, and then they decided to remove it from his arsenal.

Wrestling fans were certain this was the death of the Kane character, and while that didn’t turn out to be the case it was certainly the death of him as we had come to know him. Everything Kane had been and managed to achieve in the way of being a cold and calculating monster was thrown completely out the window in favor of a new type of monster who may have been tough, but in fact carried absolutely no mystery. The unmasking was perceived as the worst thing that could have happened to Kane, and perception is often reality.

5. Lita’s Pregnancy

The versatility of Glenn Jacobs has seen to it that the character of Kane has gotten himself into some of the most ridiculous situations in wrestling history throughout his lengthy WWE tenure. The scarred and seemingly unlikeable Kane has even seen his fair share of romance storylines involving the likes of former WWE Divas AJ Lee and Tori, but perhaps his most eyebrow-raising fling came with the insanely popular Amy Dumas, known in the ring as Lita.

This extremely bizarre storyline kicked off when Kane became obsessed with the former WWE Women’s Champion and manipulated her into having sex with him in order to protect her boyfriend Matt Hardy. She subsequently became pregnant with Kane’s baby, and after Matt Hardy left the company Kane and Lita began to bond over a miscarriage. So there you have it: Lita fell in love with her sociopathic rapist on worldwide television. That’s a story to remember and one we cannot forget, no matter how hard we try.

4. Fake Diesel

WWE Hall of Famer Kevin Nash, known then as Diesel, had come off one of the longest WWE World Championship reigns in history when he decided to jump ship to WWE’s competition, World Championship Wrestling. The character of the Big Red Machine Kane had not yet been conceived, although Glenn Jacobs was already working with the company at this point in time. His on-screen role became that of an imposter.

Jacobs began portraying Diesel; that is, an intentionally fake Diesel. This was WWE’s way of making fun of Nash after he defected, and was seen even at the time as one of the lamest storylines the company had ever attempted. It’s something that is never referred to by the company or Kane himself today and is likely something both parties would like to stay in the past, though as it lives on in infamy on the WWE Network it obviously never will.

3. Imposter Kane

The poor man’s version of Diesel was not the only fiasco related to fake versions of WWE Superstars Kane was involved with. In fact, in what may have been a bit of a case of karma coming back to haunt him, Kane himself was a victim of identity theft sometime after he unmasked and his past began to rear its ugly head, at least according to the ongoing storyline.

For weeks the date May 19 was touted as one Kane could not stand to be reminded of. It was driving him crazy and was eventually revealed to be the date his family was killed in the fire which he himself survived, set intentionally by his brother the Undertaker. When this story wound up with the 1997 masked version of his character showing up on screen next to him, things were too wacky to enjoy. Current WWE Superstar Luke Gallows was the lucky man who got to wear the awful outfit and wig, and all parties involved likely wish none of it had ever happened.

2. Katie Vick

The character of Kane has seen some of the most legendary moments in the history of World Wrestling Entertainment, but unfortunately, he has also seen some of the weirdest and most embarrassing. Sure, he was involved in the most well constructed piece of fiction ever produced during his initial rivalry with the Undertaker, has become one of the most accomplished tag team wrestlers in recent memory and even been one of the most consistent and dominant singles stars in the main event scene, but there was also Katie Vick.

Without a doubt, the Katie Vick storyline was the most bizarre and borderline offensive piece of pure garbage Kane was ever involved in. The angle saw Kane’s rival at the time, Triple H, reveal that Katie was a former love interest of Kane’s who died in a car accident the couple was involved in. According to Triple H, Kane proceeded to have sex with Katie’s corpse and The Game even reenacted the scene using a Kane mask and a mannequin. The horrible stunt was eventually dropped and never spoken of again.

1. Isaac Yankem, DDS

For his legendary accomplishments as The Big Red Machine Kane, Glenn Jacobs is almost certain to be one day recognized as a first ballot inductee into the WWE Hall of Fame. As we have seen, despite all of his incredible moments throughout his wrestling career, he has also been involved in some of the weirdest and most cringe-inducing storylines in the history of the company. However, if there is one thing Kane would prefer we all forget about above everything else in his entire career, it’s Isaac Yankem, DDS.

Isaac Yankem, DDS, was a psychotic dentist character Jacobs portrayed in his early WWE days. Yankem, who himself had horrible teeth, did not go over well with the audience and a few years back Jacobs abruptly ended an interview after the host brought up the awful, regretful character. Kane is obviously not proud of Isaac Yankem, and WWE shouldn’t be either.

Sources: denofgeek.com, wrestlinginc.com and sescoops.com