Shawn Michaels vs. The Undertaker- Bad Blood- 1997- **** 1/4
The first Hell in a Cell is the only match in this structure to be awarded five stars from the Wrestling Observer Newsletter, and while it's not that good it's an admirable introduction to the Hell in a Cell gimmick. You'd be hard pressed to find a worker better at delivering in terms of narrative in WWE than Shawn Michaels, and he's tremendous here. The match also served well to introduce a more violent Undertaker, as the match gimmick and his character became synonymous with each other. Both men do good work here with the majority of the narrative being about how much damage Shawn Michaels can take and Undertaker can deliver. There's plenty of blood and the reality of Hell in a Cell as a dangerous match is felt here in spades. The introduction of Kane is also handled well and Michaels gets away with a cheap victory after Kane interferes. Great match and only really brought down by the feeling out process of both men with the introduction of the Cell gimmick.
The Undertaker vs. Mankind- King of the Ring- 1998- **** ¾
This is the match that WWE wants you to think of when they bring up Hell in a Cell, for good reason- It's the best Hell in a Cell match performed to date. Mick Foley is one of the great death match wrestlers and he already had plenty of experience putting his body in complete peril prior to this match so of course he'd be the one to want to be thrown off the top of the cage, and god bless him for it. In terms of death match wrestling narrative Foley is the greatest I've ever seen, and this match tells a simplistic story, but a perfect one. Foley takes a few spots that are completely absurd, but like nothing else in the Hell in a Cell format, and he keeps coming back for more. At the risk of his own health he still wrestles Taker after being off and through the cell, he's obviously not well, but he's Mick Foley so he's going to do whatever it takes. This match is more a test of will, and it's like nothing else in the history of WWE and for good measure. They pushed the format as far as they could here. There won't ever be a Hell in a Cell match better than this one.
The Undertaker vs. Big Boss Man- Wrestlemania XV- 1999- *
It's a miracle that this match didn't kill the Hell in a Cell format. It's a relic of the Attitude era in the worst way possible, and ends with a mock execution. Everything prior to that moment is just two men punching and brawling each other to no fanfare. The match exists for the mock execution, and appeals to the worst kind of bloodlust of wrestling fans. It's in especially poor taste considering wrestlers have actually died in the ring.
Triple H vs. Cactus Jack- No Way Out- 2000- **** ½
To find a Hell in a Cell match not featuring The Undertaker or Triple H is a near impossibility, and this was Triple H's first one. It was also meant to be Mick Foley's retirement match, but Foley went on to wrestle for years to come in guest appearances for WWE so some of the drama of Foley fighting for his career is nullified here, but otherwise this is a stellar Hell in a Cell match. They recreate Foley being thrown through the cage and Foley and H somehow equal their viciousness of the previous month's Royal Rumble match which was no small feat. Triple H gets put over as hard as Foley possibly could and Foley goes off into retirement for a little over a month.
Kurt Angle vs. The Undertaker vs. Triple H vs. Steve Austin vs. Rikishi vs. The Rock- Armageddon- 2000- ** ½
This match is a huge mess. The big Rikishi spot looks really poor and the camera work cannot contain the action of six men working inside and outside of the Cell for over 20 minutes. Rikishi and Undertaker have no real business being here. The majority of goodwill I have for this match comes from the segments that focus on Triple H and Steve Austin. Austin never had a proper single fall Hell in a Cell match so to see him work in this environment is interesting, and he has fantastic brawling chemistry with H. They would show that again in their remarkable Three Stages of Hell match in 2001. In the end Angle gets the pin. No reason for this to have been performed in the Cell.
Triple H vs. Chris Jericho- Judgment Day- 2002- ** 3/4
A totally fine, mostly unremarkable Hell in a Cell match due to some weirdly placed overbooking with a referee who later was part of a suicide angle. Never let anyone tell you wrestling is good, folks. Wrestling is very very bad. Aside from that weird bullshit this is a fine Cell match, but doesn't really stick out among the other Cell matches in a good or bad way. I do have quite a few quibbles with the match ending on top of the cell which never feels realistic unless someone is going through the roof of the Cell. The work inside the Cell is solid, but H and Jericho have this weird stilted chemistry that can never quite get things out of gear.
Brock Lesnar vs. The Undertaker- No Mercy- 2002- ****
This is the bloodiest Hell in a Cell match which makes me actively worry about what may go down tonight between Undertaker and Lesnar. Lesnar and Undertaker have fantastic chemistry with one another (outside of WM30) and their brawling feels realistic even though they're faking punches. This one is mostly great for the mauling. It feels less like a wrestling match and more like two men just beating on each other until one finally falls. There's some good storytelling here with Undertaker's cast and a fun Paul Heyman bit as well. This is a sneaky pick for most undervalued Hell in a Cell, but I'll get to my pick for that one later.
Triple H vs. Kevin Nash- Bad Blood- 2003- * ¼
As I said on twitter this match more closely resembles two big baby men going "weeehhh" at each other while blood drips down both competitors. Finishers are traded and both men are protected and nothing matters anymore. Kliq forever motherfuckers!
Triple H vs. Shawn Michaels- Bad Blood- 2004- ****
The longest Hell in a Cell match also happens to be one of my favourites. No one is ever going to call Triple H subtle, and too often he goes for plodding "masterpiece" wrestling rather than actually just fucking going, but Michaels can reel him in, even at 47 minutes. Lesnar/Taker is the better version of this match, because it's more condensed and there's less bullshit around their "life" ending brawl, but sometimes Triple H being overwrought and just bleeding like a beautiful, long haired angel of viscus is something to appreciate.
Batista vs. Triple H- Vengeance- 2005- *** ½
Remember how I said Triple H or Undertaker have competed in like all of these fucking things? Yeah. Batista and H are better suited to wrestling with props, blood and fake violence than actually putting on a wrestling clinic so their styles mesh well here and deliver a hard hitting, physical Hell in a Cell that's missing the theatricality and narrative of previous best of Cell matches to really put it over the top. This is also the Cell match where they started fake-choking each other with a chain! Fun stuff if you're fucked up like me.
The Undertaker vs. Randy Orton- Armageddon- 2005- ** ½
This match is overbooked to hell after an otherwise appropriate start. Randy Orton is the "Legend Killer" and this is Undertaker's revenge so he just brutally wrecks him with a steel chair to start. Orton's an underrated bleeder. If there was anything the guys in Evolution did consistently well it was bleeding. Ric Flair taught them something I suppose. But then Orton starts to get some offense in and his dad gets into the ring and the urn is important and it's a huge mess. This one ends up being a big missed opportunity. Their 'Mania match is better.
D-Generation X vs. Vince McMahon, Shane McMahon and Big Show- Unforgiven- 2006- ***
This match is the jumping the shark moment for Hell in a Cell, but it's fun. It is completely obsessed with butts, balls and cock and Triple H and Shawn Michaels are bleeding EVERYWHERE. The D-X crotch chop and Vince McMahon ass kissing club are the big spots here. Big Show is only here, because he has the biggest ass and Vince McMahon loves him for that reason. Shane is here to die. Poor Shane. This match is bananas though, and I was almost positive I'd hate it, but then it just got so stupid I found it endearing. THREE STARS.
Batista vs. The Undertaker- Survivor Series- 2007- *** ¼
This is the last TV-14 Hell in a Cell. After this match the blood would be put away and a lot of the more dangerous spots would be minimized. In some ways it feels like a eulogy to the structure in this form, because a Hell in a Cell would never be worked this way again. Curiously it has the same uneasy feeling present in the first Hell in a Cell match. Hell in a Cell becomes cyclical then as Batista bleeds and bleeds, but we changed and the crowd isn't into the bloodletting anymore. WWE would go through some transitional years shortly afterward, and matches like this would rarely be seen again. This match suffers from some unsureness from the workers and a feeling of dead-air throughout the building, but like the Triple H-Batista Cell match it showcased The Animal's greatest strengths and Undertaker got to be appropriately brutal one more time.
A BONUS MATCH!
The Undertaker vs. Edge- SummerSlam- 2008- ****
Hell in a Cell has evolved over the years to mean something it didn't mean in the 90s and early 00s, but even with limitations to the brutality of the work it doesn't mean that a Cell match is inherently bad. Undertaker vs. Edge at SummerSlam is the best worked Cell match from a technical perspective and the narrative is beautiful. Edge is psychotic, but terrified of Undertaker coming back. After he destroyed Mick Foley leading up to the event he felt like he was going to take down the Dead Man. Edge comes out guns blazing, dodging Undertaker's offense and laying in his own and for the majority of this match he controls the offense, but Hell is the Undertaker's domain, and the gimmick will always call for Undertaker to be invincible in this structure. Edge pushed Taker too far, and after Taker gained some level of control he gets revenge on Edge by repeating the same moves he did to Taker during the match, the Con-Chair-To (awful pun), the spear, the steps. Then he takes Edge and chokeslams him from the top of a ladder, using Edge's fame-making weapon to his own use and sending him to literal Christian hell, because wrestling is very silly.
I am hoping that tonight's Hell in a Cell show is a good one. The Cell isn't useless, but workers have to do more with it than its godfathers by proving its destruction without a blood crutch. It has been done before, and I'm optimistic about the 2 Cell matches tonight. Reigns and Wyatt have had a good build, and Reigns has been money on pay per view this year. Lesnar/Taker offers a conclusion to a year long story, but even scarier the possibility of violence. Undertaker is 50 years old and his match shouldn't be happening on paper, but if SummerSlam is any indication he still has something left to prove. It's ironic considering his gimmick is that of a zombie that he'd still be wrestling this late into his life. Oh, and Daniel Bryan might be coming back tonight. That'd be cool.