WWE’s 10 Most Fascinating People 2020

By Rob Siebert
Fanboy Wonder

Who exactly are the “10 Most Fascinating People” in a given year? Every year when I do this list, I typically let the word fascinating speak for itself. But for 2020, a year like no other, let’s go ahead and expand on it.

Every week, these performers compete for our attention. Not just with opposing programming, but with each other. Everyone wants to be part of the story that’s the most dramatic, emotional, intriguing, inspiring, etc.

The list of WWE’s most fascinating people is a list of WWE wrestlers and personalities who, in my opinion, had the most interesting stories in a given year. They can be the culmination of a lifelong journey, as Drew McIntyre achieved this year. They can spark pressing questions, such as whether this is really the end for the Undertaker. One can even wind up on this list for the wrong reason, like Otis did with the Money in the Bank briefcase.

To put it simply: These are WWE’s most fascinating people of 2020, and these are their stories.

1. Drew McIntyre
In 2020, Drew McIntyre lived up to his old nickname and became WWE’s “chosen one,” winning the WWE Championship from Brock Lesnar.

Unfortunately, it happened at just about the worst possible time.

The COVID-19 pandemic was in its early days when Wrestlemania XXXVI took place, and the world was still coming to grips with the new rules we were (and still are) all living under. WWE was holding its televised events, including Wrestlemania, inside the Performance Center in Orlando with no fans in attendance. Thus, Drew essentially had his crowning moment in a vacuum. One might even call him “the Pandemic Champion.”

But to his credit, he forged ahead. He played the stalwart babyface we all needed to see during such trying times. He was an optimistic, hopeful babyface champion hungry to prove himself against all challengers. Mere moments after beating Lesnar, McIntyre would beat back a challenge from the Big Show. He would go on to successfully defend against Seth Rollins, Bobby Lashley, Dolph Ziggler, and Bobby Roode. He also retained twice over Randy Orton before dropping the belt to him at Hell in a Cell. Then on November 16, McIntyre would make Orton’s reign a short one, taking back the title in the main event of Raw.

Whether or not McIntyre is remembered as the champion of the “pandemic era” remains to be seen. But either way, one thing is certain: He’s been a champion we can be proud of.

2. Otis
Even if you see him strictly as a comedic character, it’s tough to deny Otis had a career year. Even if it didn’t necessarily end the way he’d have hoped.

Coming into 2020, Otis’ affection for Mandy Rose made him the lovable everyman in one of, if not the most interesting story on WWE television. The tale culminated at Wrestlemania, as Otis defeated Dolph Ziggler and got to kiss the girl. It would have been a tremendous Wrestlemania moment if there’d been fans in the building…

The subsequent decision to give Otis the Money in the Bank briefcase was puzzling. He was hot coming out of Wrestlemania. But a Heavyweight Title contender? Hardly. As such, the briefcase served to weigh Otis down more than elevate him, as fans were more interested in how WWE was going to get the briefcase off of him, as opposed to how and when he’d cash in.

It all came crashing down for Otis at Hell in a Cell. He lost the briefcase to the Miz in a match where his longtime tag partner Tucker turned on him. Adding insult to injury, both Tucker and Mandy were drafted to Raw, leaving Otis on Smackdown without his arch rival or his girlfriend.

Ouch.

3. MVP
Montel Vontavius Porter was a surprise entrant in the Royal Rumble Match. Despite being eliminated in a matter of seconds, he stuck around and became an unlikely staple of Raw.

He quickly aligned himself with Bobby Lashley, guiding him in a brief quest for Drew McIntyre’s WWE Championship. While Lashley would come up short, the duo would find new allies in Shelton Benjamin, and eventually Cedric Alexander. Together, they’ve formed the hottest, and certainly the most sharply dressed, faction WWE has seen in quite some time: The Hurt Business.

MVP’s staying power is lies almost entirely with the charisma and energy he brings to promos. But he’s also remained semi-active in the ring.

4. Dominik Mysterio
To say the very least, Dominik has come a long way since we saw him as the eight-year-old subject of a child custory storyline between his father Rey Mysterio and Eddie Guerrero.

Now in his early 20s, Dominik began making appearances with his father last year, one of which saw him brutalized by Brock Lesnar. But in 2020 he established himself as a wrestler and television character by inserting himself into the feud between Rey and Seth Rollins. As a result, he was given the extremely unenviable task of having his first televised WWE match at Summerslam against Rollins. To Dominik’s eternal credit, I thought he and Rollins stole the show that night. Yes, their match had its fair share of “gaga,” including involvement by both Rey and Dominik’s mother Angie. And yes, Dominik was in good hands with Rollins. But in the end, that match told the best story that night. Much of that can be attributed to how good Dominik has become at such a young age.

Rey and Dominik were drafted to Smackdown in October, where the emphasis has been largely on Rey’s daughter Aliyah and her storyline with Murphy. Frankly, I don’t think it would hurt Dominik to spend some time apart from his father, perhaps in NXT. Though knowing how pro wrestling works, a father/son feud certainly isn’t out of the question. Especially as we move closer to Wrestlemania.

5. The Undertaker
This was the year the real-life Mark Calaway finally came out of the casket.

After his Boneyard Match with AJ Styles proved to be the unlikely show-stealer at Wrestlemania, the Undertaker went on an unprecedented media tour to promote Undertaker: The Last Ride, a documentary miniseries on the WWE Network. In the process, he pulled back the curtain on himself and the character in a way many have wanted for the better part of three decades. No one exploited the Dead Man’s new chatty demeanor more than WWE themselves, who produced numerous Undertaker-centric specials and interviews for the network. This included two lengthy interviews with Stone Cold Steve Austin.

It all culminated in a “final farewell” at Survivor Series, which marked the 30th anniversary of the character’s debut. His farewell address was short but sweet: “My time has come to let the Undertaker rest in peace.”

But as always, whether this truly is the end of the line for the Undertaker remains to be seen…

6. Roman Reigns
“The Big Dog” was absent for much of 2020 thanks to COVID-19. But when he made his return at Summerslam, he changed the entire landscape of Smackdown with both a new attitude and a new manager.

This year saw WWE give Roman Reigns the one thing they never gave to their last poster boy John Cena: A heel run. What’s more, a damn good heel run. At least thus far. Now a full-fledged Paul Heyman guy, and calling himself the “Tribal Chief,” Reigns quickly won the Universal Championship from Bray Wyatt. He went on to have two quality pay per view title matches with, of all people, Jey Uso. At Survivor Series, he once again stole the show in a champion vs. champion match with Drew McIntyre. He capped it off at TLC, retaining his title over Kevin Owens.

All the while, Reigns has been doing the best character work of his career. He projects a quiet and intimidating menace that has made him the most interest part of Smackdown for months now. Had we gotten this guy five years ago, Vince McMahon could very well have had the new mega-babyface he obviously wanted Reigns to be so badly.

7. Lana
The way things look now, I wouldn’t be at all surprised to see Lana challenging for the Raw Women’s Title at Wrestlemania.

That may be blasphemous to some. But we all know WWE loves a good unlikely underdog story. And in trying to become a wrestler, the real-life CJ Perry is in fact an underdog. By her own admission, she’s not the most talented on the roster. While athletic, wrestling doesn’t come naturally to her. She’s also been the center of a few cringe-worthy storylines, not the least of which was her recent marriage storyline with Bobby Lashley. Did we mention her real-life husband, who now goes by Miro in AEW, was let go by WWE in April?

I invite those who would question Lana’s presence on this list to watch her episode of WWE Chronicle on the network. It’s a very revealing look into CJ Perry’s past, her mindset, and how hard she’s working to become a success in professional wrestling.

8. Randy Orton
This year, Randy Orton got back to doing what Randy Orton does best: Being a merciless, despicable heel. He does it better than just about anyone in the business today. So it’s not necessarily a surprise that in doing so, he became one of the centerpieces of Raw in 2020.

Much of it was familiar. He attacked legends like Ric Flair and Shawn Michaels, delivering his signature punt to the head. There were plenty of RKOs out of nowhere. And indeed, Orton claimed yet another WWE Championship, defeating Drew McIntyre in a Hell in a Cell Match in October.

But what once again made Orton one of the most compelling villains in WWE was what he did with Edge early in the year. The night after Edge made one of the more emotional returns in recent memory, Orton met him in the ring and proposed they reform Rated RKO. It was all a trap, of course. Orton would beat down his former friend, capping it off with a brutal chair attack (What Edge used to call a one-man “Con-Chair-To.”) This sparked a feud that went into the spring, and included Orton hitting an RKO on Edge’s wife Beth Phoenix. They had a Last Man Standing Match at Wrestlemania, and followed it up with a match dubiously titled “The Greatest Wrestling Match Ever” in June. Edge would win the former, Orton the latter. A rubber match is almost undoubtedly in the works. No doubt when it does, Orton will be as formidable and dangerous as he’s ever been…

9. Bayley
In 2020, the Smackdown Women’s Division was all about Bayley, Sasha Banks, and when their inevitable implosion would happen. The powder keg finally blew in September when Bayley ambushed Banks in the ring.

So why put Bayley on the list and not Sasha? A few reasons…

Coming into 2020, the experiment of turning Bayley heel was still fairly new. What’s more, compared to Raw Women’s Champion Becky Lynch or NXT Women’s Champion Rhea Ripley, she had by far the least buzz or momentum. Both Bayley and her championship were cold.

The alliance, and eventual feud, between Bayley and Banks revitalized the Bayley character as a villain, and thus revitalized the championship around her waist. Also a factor was the sheer length of Bayley’s run with the title. At 379 days, she’s the longest reigning Smackdown Women’s Champion of all time, and one of the longest of the modern era as well.

10. Edge
There was just something about seeing him come out at the Royal Rumble.

Edge had hit a spear during the Summerslam pre-show in 2019, which caused a little buzz about a return to the ring. That buzz increased tenfold when the wrestling news sites started reporting he’d be an entrant in the 2020 Royal Rumble Match. So it’s not like we had no clue he was coming…

But when his music hit that night, it had all the magic and grandeur it deserved. The “Rated R Superstar” had defied medical science and returned to the ring after nine years. And he wasn’t stopping with the Rumble.

The following night, Edge started a program with his former tag team partner Randy Orton that would extend into the summer. The two had a Last Man Standing Match at Wrestlemania, which would receive mixed reviews at best. They followed it up with a much better match, dubiously advertised as  “The Greatest Wrestling Match Ever” at Backlash. Sadly, Edge would suffer a torn triceps in that match that would leave him on the shelf for the rest of the year. But the smart bet is he and Orton will go one more round at this year’s Wrestlemania.

Assuming he can stay healthy, the best of Edge’s return has yet to come. Sadly, the COVID-19 pandemic has largely robbed him of the chance to wrestle in front of live audiences again. He, and WWE at large, may fare better in 2021. Either way, he’s got a laundry list of big match opponents. From AJ Styles to Roman Reigns to Seth Rollins and beyond. With luck, Edge’s comeback tour has only just begun.

Email Rob at primaryignition@yahoo.com, or check us out on Twitter.

The Silent Wrestlemania Recap – Undertaker and AJ Steal the Show!

By Rob Siebert
Fanboy Wonder

Well, alright then. Wrestlemania XXXVI (or as I call it, “The Silent Wrestlemania” happened.

Was it weird? Definitely. Awkward at times? Oh  yeah. But was it bad? No. Not even remotely.

I tweeted this yesterday, and I’ll reiterate it here: I think the world needs Wrestlemania now more than ever. So as long as it was done on a volunteer basis, Vince McMahon was right to carry on with the show in whatever form it took.

So thank you to all the wrestlers, producers, crew members, and everyone that made these shows possible.

Night One

Cesaro def. Drew Gulak.
Admittedly, I didn’t see this one. Was busy during the pre-show. But hey, technically Cesaro got a singles match at Wrestlemania. A win at that.

Alexa Bliss & Nikki Cross def. The Kabuki Warriors to win the WWE Women’s Tag Team Titles.
Was surprised they kicked off the main card with this one. Not sure if they’d have gone that route if there was a crowd. But they put on a good match.

As far as I know, Asuka and Kairi Sane were the first wrestlers of the evening to play to a crowd that wasn’t there. Since Asuka did commentary on Raw that night, it seems like these two have been asked to be louder and more obnoxious. If that’s the case, they were successful.

Elias def. King Corbin.
True story: I fell asleep during this match. No disrespect to either man. It had been a long day. I went back and watched it though. Went a little long. At least Elias actually had a match at Wrestlemania, as opposed to in-ring skits. Then again, both those skits were with John Cena. Maybe he was better off before…

Becky Lynch def. Shayna Baszler to retain the WWE Raw Women’s Title.
Good match. Wrong finish.

The psychology was right in this one. It felt like a fight. Loved the spot where Shayna whipped her head-first into the announce table. But ultimately, Shayna lost to a version of the Bret Hart “pin yourself by not releasing the hold” spot. It’s a good spot. It’s just a shame Baszler has already lost a big match to that same pinning combo. Yup, Kairi Sane beat Shayna for the NXT Women’s Title almost the exact same way at NXT Takeover: Brooklyn IV.

Between this loss, the way she lost (though that’s minor in the grand scheme of things), and the fact that an alleged killer like her couldn’t win the Women’s Royal Rumble at the number 30 spot, Shayna does not look good coming out of this.

The upside? Becky continues to dominate. Plus, my guess is these two aren’t done. And there’s plenty of room for Shayna to get even more vicious.

Sami Zayn def. Daniel Bryan to retain the WWE Intercontinental Title.
These two were the first to really take advantage of the fact that we could actually hear the wrestlers talking to one another. That played to Sami’s strengths as an annoying heel. In the end, the right guy won. There’s still a lot Sami can do as the Intercontinental Champion.

You’ve got to wonder what Shinsuke Nakamura was thinking. It wasn’t long ago that he was challenging for the WWE Heavyweight Championship at this show…

John Morrison def. Kofi Kingston and Jimmy Uso to retain the WWE Smackdown Tag Team Titles.
I give these three a hell of a lot of credit for doing a spot-fest like this without any fans in the arena. It just wasn’t the same without the crowd reactions. Although those ladder shots did sound that much more painful.

Creative finish with John Morrison plummeting to his doom, albeit with the titles in hand. Fitting for the weirdest tag team title match in Wrestlemania history.

Kevin Owens def. Seth Rollins in a No Disqualification Match.
You can argue this was the best match of night one. (More on that in a moment.) It made Owens look like a million bucks. As Raw continues to be in need of top babyfaces, that’s the best outcome they could have hoped for.

Braun Strowman def. Bill Goldberg to win the WWE Universal Title.
Yeah, this sucked.

I’m pretty sure we saw a total of two moves in this entire match. The Spear from Goldberg, and the Powerslam from Strowman. I understand Goldberg is somewhat limited in what he can do, and that this match came together on short notice. But c’mon. This was the best they could put together?

In hindsight, it was silly for me to predict a Goldberg victory no matter who he was wrestling. He does short term deals. That’s his thing.

Alright. So here we have it. Braun Strowman is the Universal Champion. I’d argue it’s about two years too late. But it happened. Now it’s all about the follow up.

The Undertaker def. AJ Styles in a Boneyard Match.
Damn. He did it again. The son of a bitch did it again. The Undertaker stole the show at Wrestlemania.

He didn’t do it alone, of course. I’ve said that we’ve reached the point where they need to use smoke and mirrors to give us a quality Undertaker match. In this case, he not only had one of the best workers in the world in AJ Styles, but the entire WWE production juggernaut backing him up.

But even so, he did it again.

Before I go any further, WWE really needs to send Matt Hardy a thank you note for this one. They deny him his ability to work creatively, prompting his departure from the company. But then Undertaker and AJ Styles have a Wrestlemania match that captures the world’s imagination using the cinematic style he essentially pioneered.

I suppose whether you call this the show-stealer depends on your definition of what a wrestling match is. Jim Cornette, for instance, would not call this a wrestling match. The cinematic presentation, the music, the special effects. It was more like a short film. I saw someone on Twitter last night ponder if this is the future of the wrestling business. I hope not. I say you can only get away with something like this once a year, if that. But if you can do it, and it works…

Not only did this give us back the dominant, tough-as-nails Undertaker that we’ve missed, it told a great story. My favorite part isn’t a particular spot or stunt. Rather, it’s when Undertaker has Styles, and he’s taunting him with things like, “What’s my wife’s name?” and “You wanna talk about how old I am?”

I don’t think you could have done this in an arena. In that sense, the current circumstances worked in their favor. But one way or another the Undertaker, along with AJ Styles, has stolen the show at Wrestlemania. In 2020. Who’da thunk it?

Night Two

Liv Morgan def. Natalya.
Nice moment for Liv, I suppose. Though I doubt anything comes of it.

Charlotte Flair def. Rhea Ripley to win the NXT Women’s Title.
If you don’t count Undertaker vs. AJ Styles as an actual wrestling match, then this was the best match of the weekend. It should come as a surprise to no one that Charlotte Flair is involved. For my money, her matches 2016 and 2018 were both show stealers.

What made this match stand out to me was the tension in the air. This Charlotte/Rhea thing hasn’t been going on that long. But if you came into this cold, you’d think they’d hated each other’s guts for years. There was just this nasty, hateful, vicious vibe in the ring. I loved it.

Does it suck that Rhea Ripley lost? Of course it does. But if you’ve been paying attention, you knew it was coming. Charlotte Flair is the poster girl for their “Women’s Revolution.” She was the inaugural Women’s Champion at Wrestlemania 32. She broke Asuka’s undefeated streak at Wrestlemania 34. She was shoehorned into the main event of Wrestlemania 35. Notice a pattern?

However, as I speculated, these two were able to have an amazing match. And that benefits Rhea much more than winning a standard one does. Her star is still on the rise. So have no fear.

Aleister Black def. Bobby Lashley.
What does it say about this match that the only thing I could focus on for awhile was the fact that Lashley was wearing pants instead of trunks.

Loved the closing spot here, the attempted Spear from Lashley into the Black Mass Kick for the win. As Lana was the one who called for the Spear, does that mean we’re headed for a Lashley/Lana split?

Otis def. Dolph Ziggler.
This match pulled off a rarity. It had the right ending but the wrong winner. Otis needed to get the girl in the end, and he did. I can only imagine the pop that kiss would have gotten in front of a crowd.

The problem I had with this one is that Dolph is one of the most decorated wrestlers WWE has had in the last two decades. Otis on the other hand, is a tag team wrestler who’s only recently made it to the main roster. Ziggler should have won. Perhaps by cheating. So Dolph wins the battle, but not the war.

Incidentally, why was Mandy dressed to wrestle? Was it just one of those “always bring your gear” kind of things?

Edge def. Randy Orton in a Last Man Standing Match.
I give both these guys a lot of credit for this one. They beat the absolute piss out of each other in front of ZERO fans. Lots of creativity on display here. In terms of fighting all over the performance center, this was exactly what you wanted it to be. I can’t say I disliked much of what I saw.

Having said that, I couldn’t believe they let Orton choke Edge with the gym equipment. It’s been a long time, but that absolutely screams Benoit. Especially because those Dark Side of the Ring episodes aired so recently.

That being said, we need to talk about something I’ll call the Lesnar/Goldberg principle. They might have had the best built match going into Wrestlemania 33. And it lived up to the hype. But they only needed about five minutes to deliver on that. It was quick, high impact, and about as concise as you could ask for. They stole the show that year.

My point is, just because a match has such an amazing build doesn’t mean it needs to go 30 to 45 minutes. Whether a match is good or not usually has nothing to do with it’s length. Triple H’s big matches tend to have a problem with this.

The Lesnar/Goldberg principle. One to live by.

The Street Profits def. Angel Garza & Austin Theory to retain the WWE Raw Tag Team Titles.

The story here ended up being Bianca Belair, who saved Ford and Dawkins from a post-match beatdown. I assume will be with the Street Profits on Raw from here on out. Works for me. She’s earned her main roster spot. Becky Lynch is also going to need new challengers in the near future.

Bayley def. Sasha Banks, Naomi, Tamina, and Lacey Evans to retain the WWE Smackdown Women’s Title.
This is another one where hindsight is 20/20. I predicted it would come down to Bayley and Sasha. But for whatever reason, WWE avoids that match like the plague. Or in this case, Coronavirus.

I was pleasantly surprised with the amount of time they gave this match. The Smackdown Women’s Division may be cold right now. But they gave these ladies a decent-sized canvas to create on.

Also…no, Michael Cole. Team B.A.D. was not a huge part of the Women’s Revolution. Just like Team P.C.B. wasn’t. And Team Bella damn sure wasn’t.

“The Fiend” Bray Wyatt def. John Cena in a Firefly Funhouse Match.
Coming into this match, I was expecting something akin to the Boneyard Match, only it would take place in some sort of demented funhouse setting.

That’s not what we got. In fact, in over two decades watching this stuff, I can honestly say I’ve never seen anything quite like what we got. It was more like a Saturday Night Live sketch than a wrestling match. It’s like they got together and said, “Bray Wyatt is crazy. So let’s just go nuts. Let’s throw shit against the wall.”

I’ll give you this much, I enjoyed its devotion to continuity. They really dove into history for this one, picking apart both characters.

I can’t say I enjoyed the Boneyard Match then turn around and say I didn’t like this one. For all intents and purposes they played by the same rules. But whereas I’d be game for seeing something like the Boneyard Match once a year, this is the kind of thing you can only do once maybe every five to 10 years.

Drew McIntyre def. Brock Lesnar to win the WWE World Heavyweight Title.
To my dismay, this match basically followed the same formula as the Goldberg/Strowman one. Hit the finishers a bunch, then have the challenger go over. In both matches it’s like they just wanted to get it over with.

Still, this one had the right outcome. Drew got his moment, unconventional though it was. One of the highlights of night two was him reaching out to the camera and saying, “Thank you.”

Congratulations, good sir. Your moment doesn’t look like anyone else’s, but it’s yours. So be proud. You earned it. You deserve it.

Email Rob at at primaryignition@yahoo.com, or check us out on Twitter.

Undertaker’s Legacy Inside the Cell: What Awaits Shane at Wrestlemania?

Undertaker vs. Shane McMahon, Wrestlemania XXXIIBy Rob Siebert
Editor, Fanboy Wonder

To their credit, WWE pulled a fast one on us by bringing in Shane McMahon as The Undertaker’s opponent at Wrestlemania XXXII. With control of WWE on the line, Vince booked his son against the Dead Man in a Hell in a Cell Match. In response, The Undertaker told Vince: “You know what I do. The blood of your son is on your hands.”

So what does he mean by that?

Since the match’s creation in 1997, The Undertaker has been in 12 Hell in a Cell Matches. His resume includes four WWE Hall of Famers, and 12 former heavyweight champions. He’s spilled blood, sent opponents sailing off the cage, and even sent one poor sap to the fiery depths. This is what awaits Shane McMahon at Wrestlemania. No wonder he’s training so hard.

So let’s look back at ‘Taker’s Hell in a Cell record. If I were Shane, I know I would be…

WWF Bad Blood 1997, Undertaker, Kane, Shawn MichaelsShawn Michaels
WWF Bad Blood, October 5, 1997.

Leave it to these two to set the bar impossibly high right off the bat.

This match has a special place in the hearts of fans for a variety of reasons. It was the very first Hell in a Cell Match, obviously. The finish famously saw the debut of Kane. But as far as the body of the match is concerned, Undertaker and Shawn had great chemistry, as they seemingly always have. They played that cat and mouse game in the cage really well. This match also marked the first time ‘Taker would throw someone over his shoulder and ram them head-first into the cage, as he’s done in various cell matches since. He also hit Shawn right in the head with one of the hardest, loudest chair shots I’ve ever seen. And of course, you have Shawn’s famous fall through the announce table while hanging off the cage. One can argue this match set the bar too high for these cell matches, considering what Mick Foley would do less than a year later. But you can’t deny the entertainment value of this confrontation. Shawn and ‘Taker took what started off as an experimental take on a cage match, and turned it into an instant box office attraction. As most of us know, ‘Taker lost after Kane’s interference. But needless to say, he’d get plenty of chances to redeem himself in that cage.

RECORD: 0-1

Mick Foley, Hell in a Cell 1998Mankind
WWF King of the Ring, June 28, 1998.

It’s the stuff of legends. While it’s one of the scariest matches WWE has ever put on, it’s also the match that has become synonymous with Hell in a Cell. In many ways, it defined Mick Foley’s career.

Most of us know it by now: A fall off the cage, a fall through the cage, two bumps into thumbtacks, and a Tombstone Piledriver. It’s the kind of match you’d never see today, and quite frankly that’s a good thing. No one should have to put themselves through this sort of thing for the sake of entertainment.

Still, the match has an undeniable magic about it. While you can’t overlook the sheer violence of it, it told an amazing story about a man’s refusal to surrender. For better or worse, Mick Foley made himself into a legend with this match.

RECORD: 1-1

The Undertaker, the Big Bossman, Wrestlemania XVThe Big Bossman
Wrestlemania XV, March 28, 1999.

This one’s better off forgotten, quite frankly. There was no way these two were going to live up to ‘Taker’s matches with Shawn or Foley. I’d have gone with something different.

Both ‘Taker and Bossman were heels. But they were doing a story where ‘Taker was trying to play mind games with Vince McMahon, and Bossman was sent in as his enforcer. It was an odd story to tell, considering Vince was still the company’s top heel at the time.

Two moments have always come to mind when I remember this match. The first is one of the low points of Michael Cole’s career. When talking about the dangers of the cell, he said: “You can get a finger caught in there!” Jerry Lawler rebutted: “After what we saw Mick Foley go through, you’re worried about getting a finger caught in there?”

The second is the post-match image of a defeated Bossman being hung from the raised cell. Considering the real-life Ray Traylor is no longer with us, it’s uncomfortable to see.

RECORD: 2-1

The Undertaker, Rikishi, WWE Armagaddon 2000SIX-MAN CELL MATCH:
WWF Armageddon. December 10, 2000.

Now this is how you end a year. Toss most of your top stars in a cage and let ’em fight for the title! One can argue this match was a precursor to the Elimination Chamber. Though no chamber match has ever been as good as this.

The match featured Kurt Angle defending the title against The Undertaker, Stone Cold Steve Austin, The Rock, Triple H, and Rikishi. Angle eventually pinned The Rock to win. But the moment everyone remembers from this match once again involves ‘Taker once again sending someone for a great fall off the cage. This time, Rikishi was the victim. Prior to the match, Vince McMahon had attempted to stop the proceedings by driving a demolition truck into the arena. The bed of the truck would later be used as a landing site for Rikishi, when Undertaker pushed him off the top of the cage. It was choreographed to look like a chokeslam, but he pushed him. The sight of a 400 lb man falling from that height certainly sticks in your mind.

RECORD: 2-2

The Undertaker, Brock Lesnar, WWE No Mercy 2002Brock Lesnar
WWE No Mercy. October 20, 2002.

One can make a solid argument for this being ‘Taker and Brock’s toughest, nastiest battle. It was certainly their bloodiest. WhatCulture.com recently called this match one of WWE’s bloodiest of all time.

This was during the era when Paul Heyman was writing Smackdown, so it’s not surprising that this story had a lot going on. What’s more, Heyman was still managing Brock at this point. ‘Taker’s then-pregnant wife Sara had been used to put heat on Brock and Paul, and make things personal. What’s more, Brock had (kayfabe) broken Undertaker’s hand, which weakened the Dead Man during the match. But on the flip side, ‘Taker was allowed to use the cast as a weapon.

With its sheer violence and bloodshed, this match was one of the earliest to illustrate that Hell in a Cell Matches didn’t have to be about stunts on top of the cage. With the right wrestlers, the really twisted stuff happens inside those walls. While ‘Taker put up as valiant an effort as ever, Brock emerged victorious. Bloody, but victorious.

RECORD: 2-3

The Undertaker vs .Randy Orton, Armageddon 2005Randy Orton
WWE Armageddon. December 18, 2005.

This was a culmination of a year-long program between The Undertaker and Randy Orton. On paper it’s a tremendous main event. But this was the first cell match I can remember seeing and simply going: “Meh.” It was by no means a bad match. But it lacked a certain special something that we’d come to expect from Undertaker’s matches inside the cell.

Still, it had its share of good imagery. Orton was bloodied early on, and there were some nice shots of him getting raked against the cage, and crawling on the mat outside the ring. While it’s not always a thrilling match, it is a nice reminder of just how good Orton was in the early stages of his career. We also had “Cowboy” Bob Orton out there with his son, which added a little garnish to things. A good match, which Undertaker won with the Tombstone. But it lacks a certain something to be called one of his best in the cage.

RECORD: 3-3

Undertaker, Batista, Hell in a Cell, Survivor Series 2007Batista
WWE Survivor Series. November 18, 2007.

As was the case with Orton, Undertaker had been working with Batista on and off since Wrestlemania. But Batista had better chemistry with ‘Taker than I think anyone expected. They were able to being out the best in each other. They stole the show at Wrestlemania XXIII in Detroit, and had been having consistently good matches since. This was essentially their blow-off.

‘Taker put a new spin on an old trick out in this match, placing the thin end of a chair against Batista’s throat and then ramming it into the ring post. Batista later had a nice counter, turning “Old School” into one of his trademark spinebusters. He got a major coup toward the end, hitting his Batista Bomb on The Undertaker through a table. ‘Taker would regain the advantage hitting a Tombstone, and then a second one on the steel ring steps. It had been a battle worthy of their rivalry, until Edge emerged to cost Fittingly, Edge and Undertaker would go on to main event Wrestlemania XXIV, and then find themselves back in the cell almost a year later…

RECORD: 3-4

The Undertaker, Edge, Summerslam 2008Edge
WWE Summerslam. August 17, 2008. 

Undertaker and Edge had done quite a bit leading up to this one. They’d main evented Wrestlemania, they’d had a TLC Match, and now they were trying to cap it off inside the cell. And to their credit, they did just that.

In terms of WWE-style brawls, this match had almost everything. They wasted little time getting to the weapons and chaos. We had steel ring steps, we had a table, we had a chair, and eventually two ladders were introduced. This was almost a hybrid Hell in a Cell/TLC Match. And we saw that vicious heel side to Edge that had emerged since he’d started his now legendary heel run. He even speared Undertaker through the cage wall, and the action spilled on to the outside. Years later, Edge would reveal on Talk is Jericho that he’d wanted to take a Tombstone on top of the cage.

They went for sheer brutality mixed with iconic imagery for the finish to this match. After brutalizing Edge with a chokeslam through two tables, a shot with a TV camera, and “Con-Chair-To,” the Dead Man hit the Tombstone and got the pin. But for the grand finale, ‘Taker would chokeslam Edge from a ladder, through the mat. Moments later, the ring interior would erupt in flames. To cap off a match truly worthy of both The Undertaker’s Hell in a Cell legacy, and the spectacle of Summerslam, the Dead Man had sent his rival straight to hell…

THE RECORD: 4-4

CM Punk, The Undertaker, WWE Hell in a Cell 2009CM Punk
WWE Hell in a Cell. October 4, 2009. 

The first Hell in a Cell pay per view featured an eye-rolling three cell matches. Undertaker and Punk were up first, in what wound up being one of the shorter cell matches ‘Taker has ever been in.

Considering what they’d go on to do at Wrestlemania XXXIX, one has to wonder what ‘Taker and Punk could have done here had they been given more time. But considering what ‘Taker had done in these matches in the past, this was pretty standard by comparison. Granted, they had two more of these matches to go that evening. But come on, it’s The Undertaker…

Still, ‘Taker wound up winning the World Heavyweight Title from Punk that night after a Tombstone. So for Undertaker fans, the result wasn’t something to gripe about.

RECORD: 5-4

The Undertaker, Kane, Paul Bearer, WWE Hell in a Cell 2010Kane
WWE Hell in a Cell. October 3, 2010.

This is another one of those matches that on paper is fantastic, especially if you’re an Undertaker fan. You’ve got Kane defending the World Heavyweight Title against his brother, who has Paul Bearer back in his corner. They’re in a match The Undertaker made famous, and Kane made his debut. They’re free to do just about anything to each other. The pieces are in place for an epic confrontation.

There was nothing epic about this match.

I take no joy in saying that. But this match is a big part of the reason people aren’t clamoring for one last Undertaker/Kane match. These guys were slower than molasses, and in the end just…sad. I’ll give them credit for one thing, though. The finish saw Paul Bearer turn on The Undertaker for what he did to him several years prior in a “Con Crete Crypt Match.” WWE pays attention to continuity when they want to, and in this instance it paid off. It’s just too bad the match didn’t deliver.

RECORD: 5-5

Wrestlemania XXVIII, Undertaker, Triple HTriple H (Guest Referee Shawn Michaels)
Wrestlemania XXVIII. April 1, 2012.

This match was billed as “The End of an Era.” But they could just as easily have called it the Hell in a Cell All-Star Game. The only person who might be considered as synonymous with the cell as The Undertaker is Triple H. Now they were facing off in the cage, with the other pioneer of the cell, Shawn Michaels, as the guest referee. These three simply being in the ring together had an epic quality to it. What’s more, this was ‘Taker’s 20th appearance at Wrestlemania, and the finale of a story they’d been telling at the previous three Wrestlemania events with these iconic stars.

To their credit, they made us believe Undertaker’s Wrestlemania streak was truly in jeopardy. Triple H used the steel ring steps, a chair, and his trademark sledgehammer on the Dead Man. But the one spot that really sticks out in this match is the one where Shawn superkicks ‘Taker, sending him straight into a Pedigree from Triple H. When ‘Taker kicks out, Shawn looks absolutely terrified, as if he’s just witnessed something supernatural. He’s one of the best actors the business has ever seen.

And of course, after ‘Taker’s win, the three of them walked up the ramp together, bringing tears to the eyes of many a fan who grew up watching them perform. What a match, and what a moment in Wrestlemania history.

RECORD: 6-5

Brock Lesnar, Undertaker, WWE Hell in a Cell 2015Brock Lesnar
WWE Hell in a Cell. October 25, 2015. 

Over 18 years after his first cell match, I’m amazed ‘Taker is still having these matches, much less against somebody like Brock Lesnar. But low and behold, there he was. And they even surprised us by getting some color.

More than anything, I remember just how snug these guys were in this match. Lesnar in particular was just beating the crap out of ‘Taker. And early in the match he hits him with a chair shot that’s pretty stiff.

Midway through the match, Brock rips up the canvas and padding on the ring, exposing the wood underneath. That’s something we hardly ever see, and it’s a unique sight to be certain. They played it up, as ‘Taker gave Brock a chokeslam and a Tombstone on it. But in the end, they tied this story up nicely with a bow, as Brock gave ‘Taker a dose of his own medicine. The Dead Man had been gaining unfair advantages over Brock for months by hitting low blows. But on this night, Brock hit ‘Taker below the belt, got an F5 on the exposed wood, and the pin. Not the best Hell in a Cell Match by any means, but it gets points for being hard-hitting.

RECORD: 6-6

Images 1 and 3 from ringthedamnbell.blogspot.com. Image 2 from prowrestling.wikia.com. Image 4 from natureinyourhand.blogspot.com. Images 5, 6, 11 and 12 from wwe.com. Image 7 from pwpnation.com. Image 8 from mediaspo0rt.com. Images 9 and 10 from bleacherreport.com.