It’s Wrestlemania day, and, despite appearances to the contrary last year, this really does look like its going to be the year we see the swan song for the greatest professional wrestling character ever: The Undertaker.
Of course when you think of the Dead Man, his name is almost synonymous with Wrestlemania, having appeared at 25 of the last 27, and amassing an insurmountable 23 out of 25 wins. With that in mind I thought I’d take the time to go back over the legendary Wrestlemania career that Taker has had. and rank the matches from worst, through to the very best
25: Giant Gonzalez - WM9 - There is very little to be said about this utter turd of a match. Far from the masterpieces we will see down the list, this was a particularly low point on what is considered the worst Mania ever. Gonzalez was big and hulking yes but a good worker he was not, and even the Undertaker’s obvious skill couldn’t sort this out. It ends with Gonzalez choking Taker out with Chloroform and getting DQ’ed. I just… Nope, I got nothing. It was a turd. A complete total turd.
24: Jimmy Snuka - WM7 - At just over 4 minutes, the Undertakers first Wrestlemania appearance felt more like an extended squash match than anything particularly special. Its not bad for what it is, just very basic. He can (and will) do substantially better).
23: Big Boss Man - WM15 - For my money the worst Hell in a Cell match in WWE history, this is a Boss Man who never really gets going. Following the brutality of the Michaels and Mankind HiaCs this just feels entirely forgettable, something that cage should simply never allow.
22: King Kong Bundy - WM11 - Another quick fall, this feels at least a little more accomplished than the Snuka match, and did what it needed to to continue the ongoing story with Ted Dibiase which the Undertaker was working up to at this point.
21: Shane McMahon - WM32 - The lowest recent entry on this list, its the storytelling more than the match quality that let this down. Shane is still willing to do all his crazy stuff, and the Undertaker gets all his stuff in, but it just never made sense why Undertaker was doing Vince’s dirty work to begin with. Taker is ostensibly still a face here, and yet he’s fighting for the heel head of the company against a massively over returning Shane. And WHAT WAS IN THE LOCK BOX?! 2 years on and we still never got the end of the story.
20: Sycho Sid - WM13 - Sid, like Gonzalez above, was never a fantastic worker in the ring, and while he puts on a serviceable match here, its not what anyone remembers from this card - thats the Hart Austin submission match.
19: Jake Roberts - WM8 - The last of the very early matches we will cover, and again this is really before there was a Streak to defend. This is still very early in the career of the Undertaker and this squash match allows us to further that character in the eyes of the audience.
18: A Train and Big Show - WM19 - Notable for being the only non one-on-one match the Undertaker has had at the Show of Shows, this is 3 big men going at it. It might not be a masterpiece, but its a good hard hitting match.
17: Mark Henry - WM22 - For someone like my self who would call himself an Undertaker superfan I’ve never actually been all that partial to Casket matches, despite them being his signature. The gimmick rather detracts from the suspense of the big near falls which can make big matches feel even bigger, but again this is a decent big mans wrestling match, even if the suspense is never right where it needs to be
16: Kane 1 - WM14 - One of the best storylines Undertaker had been in up to this point saw him refuse to fight his brother, who was wreaking havoc in the WWE and consistently making Taker’s life hell. To see the two brothers finally come to a head, and for it to take 3 Tombstones to put the Big Red Machine down made both men look like monsters, which lets face it - is kind of the point.
15: Diesel - WM12 - On the ongoing subject of big men knocking bells out of one another, comes the Diesel match. I’m sorry to say this, and I know I’ll get flack for it from some in the Internet wrestling community - I’ve never really rated Kevin Nash as a performer. It may just be that you had to be around at the time to truly feel what he would become with the NWO, but I just never cared for him. Its why this match came as such a pleasant surprise because it feels like a bit of a high point for Diesel match quality wise.
14: Brock Lesnar - WM30 - Its a crying shame that the match which ended the Streak is so low down this list. From an importance stand point it could easily be higher but - having suffered a concussion just a minute or two into the match - the pace is completely thrown off, and it never really regains it. If the ramifications of the final moments weren’t there, I don’t think this match would even be in the conversation. Its a mess, but an honourable mess, and we have to give kudos to Taker just for keeping going in the condition he was in. And lets face it: the sheer importance of the end of the Streak makes this one of the most important Wrestlemania moments of all time even if the match itself doesn’t stock up
13: Bray Wyatt - WM31 - Thankfully it seems time heals all wounds. The broken Dead Man we saw just a year earlier losing the final Streak match would return seemingly rejuvenated. The result was never really in question, but it was nice to see someone of Wyatt’s stature in the WWE system at the time get the opportunity at such a high profile match. I’ve long been high on Bray Wyatt as a character and while its often felt he has been allowed to stagnate, at least at this point creative were clearly interested enough in him to hand him to the Dead Man.
12: Ric Flair - WM18 - On a night which saw Hogan vs Rock main event in an Icon vs Icon match that would go down in history, a little way down the card Flair and Undertaker too were looking to put on a huge legends match. WCW’s biggest star had come back to the WWE and the Undertaker was realistically the gatekeeper. A bloody affair with Flair donning his patented crimson mask early on in the proceedings, its a match which probably doesn’t get the credit it deserves given the match which came later in the night, but its definitely good. It also ends with Undertaker holding up 10 fingers, signifying his 10-0 record at Wrestlemania, the first time on television that the Streak had really been mentioned, and it wouldn’t come into its own for another several years - on which more later.
11: Batista - WM23 - By this point The Streak was in full swing, and The Undertaker was really reaching the peak in his career. It was The Streak Vs The World Heavyweight Championship, and for my money this was Batista’s best feud in the WWE. The two big men put on a hard hitting contest. A thunderous Batista Bomb came close to ending the Streak, while the Animal kicked out of The Last Ride, as the pair traded near falls. At a little over 16 minutes this was better than it ever deserved to be, and like I say: might just be one of Batista’s very best matches.
10: HHH 1 - WM17 - Another match which gets lost in the shuffle of the card it was on. WMX7 is for many the best Mania ever, and includes the best TLC match ever, and the best match of the Austin Vs Rock trilogy. That said this for me is the Undertaker’s big Mania coming out party where the matches really started getting good. They battle all over the arena. Chair shots, sledgehammers, a classic ref bump (seriously Mike Chioda, an elbow drop doesnt knock you out for 10 minutes), this was a properly fantastic match and a prelude to the two classics Hunter and Taker would later put on.
9: Randy Orton - WM21 - Above we mentioned the first time the Streak would really be called out as such, and this is the match. At this point deep into his Legend Killer gimmick Orton swore to do what 12 men hadn’t been able to do up to that point: Beat the Dead Man at the Show of Shows. This feels like the closest the booking ever came to ending the Streak before it actually happened, and the match is properly impressive. It was completely believable that Orton might have the rocket strapped to his back, and a win over Undertaker would have sent his stock into the stratosphere. Some interference from Bob Orton and an incredible Chokeslam-into-RKO reversal stand out as the high points of this superb match, but in the end its Randy’s hubris which gets the better of him. Determined to beat the Phenom with his own move Randy goes for a Tombstone which Taker flips back into his own for the win. 13-0, and the Streak marches on.
8: Roman Reigns - WM33 - I’m going to get a lot of flack for this going as high as it is. I’m not going to claim it has the match quality of some of the entries we are about to see, but the sheer weight of the emotion in this match was palpable from the get go. The moment Jim Ross came out to commentate, and the fact the match was the main event, fans had an inkling that this might just be the Undertaker’s Last Ride. A back and forth battle between the two would culminate in what many assume was the final time we will see The Dead Man, at least in that gimmick. He leaves his hat and gloves in the ring as an entire stadium gives this man a standing ovation, not a dry eye in the house. It may not be an INCREDIBLE match bell to bell, but its serviceable enough that the added emotion makes this chapter in the Undertaker’s legacy feel so important.
7: Kane 2 - WM20 - Another match more about the story than it was about the action per se, but what a story it was. The November before, the American Bad Ass version of Undertaker had lost a Buried Alive match to Mr McMahon after his brother Kane ceremoniously dumped an entire JCB load of dirt on the Biker. Over the next several months Kane became haunted by visions of the Undertaker, with the signature lightning bolts and gongs. Kane carried the brunt of the feud as Undertaker was intentionally kept off screen, but the Big Red Machine does an incredible job of playing up how he doesnt believe in the magic of the Undertaker. He believes the Dead Man is gone, and that he won. Then when Mania finally rolls around, the druids march out with their torches, Paul Bearer walks out with the Urn, and then there he is. The Dead Man has risen, black trench coat, black hat, this is THE UNDERTAKER. The Phenom. The Bad Ass might be gone, but the most powerful entity in the WWE is back. He makes short work of his brother and proves to everyone in attendance why he is the Dead Man. On a rewatch you could probably skip the match itself, but the promotional video and then the entrances are probably the best production WWE has ever done. There, I said it.
6: CM Punk - WM29 - This is the point in our list where we reach the real masterpieces. From this point onwards it would almost be fair to say that on any persons given list these could easily go down as a person’s favourite Mania match for the Undertaker. Having held the WWE title for longer than anyone in the modern era, CM Punk made no secret of the fact he believed he belonged in the main event of Wrestlemania 29, but with Rock Vs Cena holding that coveted spot, Punk would have to find another way to the show of shows. With the death of Paul Bearer, Punk gets to go into full heel mode as he steals the Undertaker’s urn, mocking the memory of Bearer and calling out the Dead Man.
5: Edge - WM24 - Featuring two of my all time favourite superstars, this is a match I have been back to many times over the years. Edge was able to counter the Dead Man time and again, with Undertaker unable to hit almost any of his signature moves to put the Rated R Superstar away. A ref bump which would lead to a reverse Tombstone spot which would echo the earlier Randy Orton effort, and an incredible reversal of Edge’s spear into a Hells Gate would ensure the Streak would last on another year.
From here the list gets even more interesting. These last four matches for me could almost be interchangeable in their position on this list, because to be honest: They are one ongoing story. It may technically be four matches, but for me WWE has never so successfully woven a story across four consecutive years as they did when The Undertaker would come face to face with HHH, and the Heartbreak Kid Shawn Michaels. That story is something we shall examine now. I will give them in my order of preference, but as I say, this is one of those where all four matches are practically perfect and I wouldn’t argue anyone who put the four matches in a different order.
4: HHH 2 - WM27 - Having watched his best friend Shawn Michaels be unable to beat The Undertaker not once but twice at Wrestlemania, and retire in the process, The Game had a lot to prove going into WM27. He had to beat the Phenom or die trying, and this is one of the most heart hitting battles of the entire streak. Chair shots, and an amazing camera shot as HHH delivers a Tombstone to Undertaker, trying to put away the Dead Man with his own move stand out. Its one of a hundred fantastic moments in the match, and its place in the ongoing story cannot be downplayed. The Undertaker being unable to walk out under his own power at the end of the match was a huge moment. The Dead Man suddenly felt a little more mortal, and even though the Streak remained, maybe, just maybe, it was beatable after all? It had to be worth just one more try right? On which more soon.
3: Shawn Michaels 2 - WM26 - Its not QUITE the high water mark of their first contest (darn it, that feels like a Spoiler, though you’ve all guessed already where I’m going), but Shawn’s retirement match is FULL of raw emotion. They trade false finishes back and forth for what feels like an age, but not for one moment does anyone want to see this instant classic end. This is a battle for the ages, and as the final 3 count falls it feels like we have witnessed something truly special.
2: HHH 3 - WM28 End of an Era Hell in a Cell, Shawn Michaels as Special Referee - This was very nearly top of my list. Its the culmination of the story these 3 men have been telling for four years. The Undertaker is the most vulnerable we have ever seen him up to this point after WM27 and we literally have not seen him on screen in a full year outside of some strange video packages. This time it is HIM who needs to prove something. He wants HHH because he needs to know. He doesn’t feel like his win counts the last time because it was he who was broken by the end. He wants one final match to settle it all. The addition of Michaels at the ref is the best touch, because the audience knows his history with the Undertaker, but also his history with HHH. They’re friends yes but there has also been huge animosity between them. Could Shawn bare to see Hunter do what he couldn’t and snap the Streak? Some frankly fantastic psychology goes in to this, but the match reaches its peak when Undertaker snaps at Michaels and puts him into Hells Gate, prompting Michaels to then give Sweet Chin Music directly into a Pedigree for what might have been the closest near fall of the entire Streak. This is probably one of the matches (along with Number One on this list) that I have seen more than any other, and I still explode into floods of tears seeing the curtain call at the end. Three men who gave EVERYTHING to a business they love, and to fans who loved them, and they are going out on a high. If I’m honest, I’d have liked this to be the end of all 3 men. Have Hunter go off into his exec job and have Shawn and Taker ride off into the sunset. They never bettered this with what followed, so quit while you’re ahead.
1: Shawn Michaels 1 - WM25 - It was never really in any doubt was it? As a lifelong Undertaker fan (anyone who knows me knows that he is my favourite wrestler), this is for me not only the best Undertaker Wrestlemania match, this is the single greatest professional wrestling bout ever. I have seen it easily 100 times, and could practically take you move by move. Right from the Heaven Vs Hell entrances, to the moment where Shawn pushes the camera guy in front of a diving Taker, to the moment which lead to my favourite gif ever (Taker’s SHOCKED eyes after Shawn kicked out of a Tombstone). This thing is a masterpiece from bell to bell, and, nearly 9 years later its still never been bettered by any pair of performers. I just don’t know how else to say about this. I don’t think there is any wrestling fan alive who I need to tell how good this was. Instead of rambling on I’ll say this instead: save the time you’d have saved reading an essay on how incredible this is, and go watch this match again on the WWE Network right now. Do it. Right now. You will not be disappointed.
With Wrestlemania 34 just hours away, we have to wonder whether he will answer John Cena’s challenge, and - if he does - where the match would fall if I was to redo this list after the event. Only time will tell, but for now lets simply celebrate the most important WWE career of all time. Thank You Undertaker. If this is to be the end, I just want to thank you for so many great memories.
