Cactus Jack battles Triple H inside Hell In A Cell.
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Gather around, kids. You see, there was a time when a Hell In A Cell match was something special. Something rare. And it was a lot easier to figure out what was the best Hell In A Cell match of all time.

But that time has passed. Hell In A Cell is a gimmick pay-per-view, sometimes with up to three matches inside the demonic cage. What’s special about the match has faded into memory.

And that makes the good ones really stand out. Even after years of annual Hell In A Cell matches, the great ones are still fresh. What worked about them still works.

Here’s our list of the five best Hell In A Cell matches of all time.

Spoiler: I really hope you guys like the Undertaker.

Mankind atop the Cell.

5. The Undertaker Vs. Mankind (King Of The Ring 1998)

I know, I know, why is this at number five? Well, it’s time someone leveled with you folks.

This match sucks.

Simply put, as a match, a story, as a choreographed, violent dance between two monsters, it sucks. There are two reasons this match is among the best Hell In A Cell matches.

The first reason is that Mick Foley is a crazy person. And the second reason is that Mick Foley is apparently an even crazier person when he’s severely concussed.

From the opening bell, when Mankind — for no reason at all, mind you — climbs straight to the top of the cage until his ultimate defeat at the Undertaker’s hand, this match is sheer nonsense. It’s a pretty good microcosm of the entire Attitude Era. Or at least Vince Russo’s handling of it. Style over substance. Flash over story.

And for all the complaining I do about everything except those two spots, I still love it. It put Mick Foley back on the map after he started to languish a bit, and it kept Undertaker in the thick of things leading to his match with Austin at SummerSlam 1998.

Sometimes a warm memory or two is all it takes to make a list. And that’s exactly what puts this one on our list of the best Hell In A Cell matches ever.

The Deadman beats the Rated-R Superstar

4. Undertaker Vs. Edge (SummerSlam 2008)

It’s strange that it took until 2008 for Edge to get a high profile match like this against the Undertaker. Let alone one good enough and big enough to be considered one of the best Hell In A Cell matches ever.

They battled prior to this, but much of Edge’s time as a top guy was spent feuding with John Cena. For that reason, he never really felt “real” until this match.

But oh MAN, was he for real after this match. He passed the proverbial “top guy” test — he survived a brutal spotfest with the Undertaker.

This match had a little bit of everything, but it never became obnoxious. Sometimes these matches go too far; sometimes there’s a reason not to throw the kitchen sink in.

And Edge and Undertaker rode that line, with equal parts madcap violence and storytelling. Edge was already a superstar heading in to this match.

By the end of it, he was a for-sure Hall of Famer.

Michaels raises Undertaker's hand.

3. Undertaker Vs. Triple H – End-of-An Era Match With Referee Shawn Michaels (WrestleMania XVIII)

Okay, so what I said about the kitchen sink before? Yeah, forget that.

The feud between the Undertaker and Triple H wasn’t exactly the stuff of legend. Both guys are legit legends themselves, but the build-up to this match wasn’t the greatest.

WWE’s story for the match was simple and enjoyable enough. Triple H failed to beat the Streak the previous year at WrestleMania XVII, so he decided to have another go at it. Inside the Cell. With his best friend (who lost his career to the Undertaker two years earlier) as the referee.

But the execution of the feud and the angles wasn’t the greatest. Which meant that the match had to be. And for all the overbooked shenanigans, it wound up being one of the best Hell In A Cell matches ever.

Triple H never had a chance, but there were moments (especially considering Michaels’s allegiances) where he and Undertaker tricked us into thinking the Streak might end.

It’s those moments of uncertainty that makes us wrestling fans. Those moments when we forget it’s all a work. It’s not particularly revered by most fans, but I truly look at this as one of the best Hell In A Cell matches of all time.

HBK survives the first HIAC match.

2. Shawn Michaels Vs. The Undertaker (In Your House: Badd Blood 1997)

You never forget your first.

The first Hell In A Cell match could very easily be the best Hell In A Cell match of all time. And I wavered with this one. In the planning for this piece, numbers one and two switched places quite a few times.

They’re both perfect, so the numbering is more of a formality than anything.

Shawn Michaels and the Undertaker set each other on a collision course at SummerSlam 1997. Michaels was refereeing the Undertaker’s WWE Championship defense against Bret Hart. And when the Hitman pushed him too far, Michaels swung a chair at the Excellence of Execution. Trouble is, Bret ducked, and Michaels whacked Undertaker in the face, costing him the championship.

HBK and the Deadman crossed paths a few times on the road to this match. But thanks to Michaels’s DX cronies, there was never a decisive finish. Hence, Hell In A Cell.

If you ever doubt that Shawn Michaels is the greatest of all time, watch this match to snap yourself back to reality.

And then there’s the finish with the debuting Kane. Fantastic stuff from start to finish and a testament to why 1997 was WWE’s greatest creative year in history.

Triple H defeats Cactus Jack in the best Hell In A Cell match of all time.

1. Cactus Jack Vs. Triple H — If Cactus Loses He Must Retire (No Way Out 2000)

Believe it or not, there was a point in late 1999 when there were concerns about whether WWE could stay on top of the wrestling world.

Steve Austin was injured and out indefinitely. The Undertaker was injured as well. Everybody knew the Rock had “superstar” written all over him, but they weren’t sure if he could carry the company.

And worst of all, Triple H was not yet a proven commodity as a top star. Enter Mick Foley.

As Cactus Jack, Foley built a superstar out of Triple H in their street fight at Royal Rumble 2000. A month later at No Way Out, Foley cemented Triple H as a superstar.

Triple H, the WWE Champion, was riding high after defeating Cactus Jack and was looking ahead to WrestleMania 2000. But Cactus wanted one more bite at the apple.

So the Game made a deal: Cactus could pick the stipulation, but Triple H wanted Cactus’s career on the line.

That was fine with Cactus Jack. The stipulation? Hell In A Cell.

Cactus pulled out all the stops in what he truly intended to be his final match. It wasn’t, though, because wrestling. But there was a battle on top of the cage, a flaming 2×4 wrapped in barbed wire, and Triple H throwing Cactus off of and through the cage. That’s not what made the match special, though.

It was all about story. Like the Badd Blood match before it, this was perfect combination of action, violence, and storytelling.

All of the elements for a great match were there. And that’s why this is the best Hell In A Cell match ever.

The Breakdown

Any list is subjective. Five different people will come up with five different lists of the best Hell In A Cell matches of all time. And they’ll all be right.

The matches on this list are more than mere tributes to violence and mayhem (well, I guess you could make an argument for number five). They’re stories. And you can follow the story of any one of them, without knowing anything about the rivalry that led the competitors there, just from watching the matches.

Everything you need to know is going down inside the cage. That’s why these five contest are the best Hell In A Cell matches ever.

All images courtesy of WWE.

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