365 matches in 365 days, each from that specific date on the calendar? Challenge accepted. Welcome to 365 Wrestling.

Wrestling fans can debate and argue over anything: whether they choose to do so in public, on message boards, or via social media. What makes someone a good wrestler? What makes a good match? And, when evaluating a match, how much does what happen before and after the bell influence things?

This latter question is an excellent one to consider, as it pertains to this entry of 365 Wrestling: The Undertaker taking on Hunter Hearst Helmsley in this episode of Shotgun Saturday Night from 1997.

Lest we offend the copyright gods, I’ll just tell you you can find this match on YouTube through a little bit of shrewd searching.

The Context

You probably know him better now as Triple H, the many-time champion turned high-ranking executive and son-in-law of Vince McMahon himself. We’re a far field away from Hunter having that level of prominence and power here. He’s still firmly entrenched in the upper midcard, and using his snobbish character. Helmsley is Intercontinental Champion here — the first of his five reigns — and the title is on the line.

Undertaker is entrenched firmly as one of the WWF’s top and most popular acts. He’s also on his own at the time of this match, having split with Paul Bearer at Summerslam the previous year.

The match itself happens on Shotgun Saturday Night, which started at the beginning of 1997. The initial goal of Shotgun Saturday Night was to present an edgier product than typical WWF programming, and the initial run of episodes, which actually ended here, occurred at unlikely venues for wrestling all over New York City — such as Penn Station, the site of this match.

I was surprised to find out that these two already had had several singles matches before this.

The Match

There are two ways to look at this match.

If you’re going to judge solely by what happens from bell to bell, you’re going to be disappointed. There’s a commercial break right as Undertaker hits the ring, at which point Helmsley jumps him. When the action resumes from the break, the referee gets sandwiched in the corner and Hunter wallops the Deadman with his title belt to gain the control… only to go to another commercial. Back from the break, and the action is moving at a brisk pace, although most of it unfolds in the punchy-kicky style that was more common than it should have been during the Attitude Era. The match ends when Undertaker drills Helmsley in the head with the belt, as payback for what happened earlier. However, this vengeance happens right in front of the referee, leading to a quick DQ.

If you’re going to judge this match from the beginning of entrances all the way through the post-match, it gets elevated to another plane. The setting — smackdab in the middle of Penn Station — adds so much to the presentation. Helmsley arrives in a stretch limo that pulls up outside, says a few quick words about how he wouldn’t get caught dead riding one of the trains at the station, and then descends a staircase into the concourse. Undertaker’s entrance is even more surreal in the context of Penn Station. After getting down the stairs, he makes his way to the ring through the crowd.

The setting stands out because it is so unlike standard WWF/WWE programming, which usually seeks a sameness from show to show and week to week… and has since the promotion truly “went national” in the late 1980s. Here, we get wide panning shots to take in the crowd and the limited space, unlike the glut of camera cuts that embodies current programming from WWE. The ring looks considerably smaller than the 20-by-20-foot squared circle WWE typically uses. It catches the eye and draws your interest.

The post-match is the best part of the entire endeavor. Frustrated at the DQ and Helmsley’s chicanery, Undertaker delivers a chokeslam (even while the fans chant for a tombstone). Helmsley tries to retreat and a chase ensues up the stairs, until the Deadman grabs Hunter and delivers a tombstone at the top of the escalator. Helmsley stands tall, soaking in the cheers of the crowd as Helmsley’s unconscious carcass heads down the escalator.

Random Thoughts

–Vince is on commentary and if you’re up for a quick drinking game that will lead to a buzz, do a shot every time he says “what a maneuver!”

Sunny joins Vince on commentary. It’s easy to forgot how smooth and comfortable she was as a talker.

–For some reason, Vince describing Helmsley as “Mr. Pompisity” cracked me up.

–It’s a shame the WWF strayed away from the format on these initial episodes of Shotgun Saturday Night. Instead, the show quickly became a B-show that was held at the same venues where Monday Night Raw was filmed. I’m a big fan of wrestling filmed in unique venues with the opportunity for unusual angles.

–So, fun fact, my original plan for this entry was going to be Katsuyori Shibata vs. Tomohiro Ishii from New Japan in 2016. Except that match happened on February 11, not the 8th! Calendar fail … for what it’s worth I was already a bit dodgy about it, because those Shibata headbutt spots are downright uncomfortable to watch after a similar headbutt against Kazuchika Okada ended Shibata’s career and nearly killed him.

Final Rating: 6.1

The atmosphere, the entrances, and the post-match make this highly entertaining even if the in-ring action is nothing special. Given the status that both Undertaker and Triple H have achieved in WWE lore since then, it’s surprising to me that this match — and especially the tombstone on the escalator — aren’t remembered or called back more often through the years, or at least got more notice while both were active wrestlers.

Here’s the complete, ongoing list of matches in this project.

Up Next

We head south of the border for trios action.

I love having feedback from readers. Send it to me — good or bad — along with any match recommendations you have! Just reach out on Twitter or fill out the contact form on the site.

4 thoughts on “365 Wrestling, Day 39: Undertaker vs. Hunter Hearst Helmsley (WWF Shotgun Saturday Night, 2/8/97)

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