There have been some awful King of the Ring pay per views (1995, 1999, and 2002, I'm glaring at all three of you), but the novelty of the event in itself is definitely missed. Through 10 pay per view iterations, King of the Ring became an event that you'd look forward to, kind of a B-grade version of the Royal Rumble in that one would develop a curiosity toward the eventual winner, and the push that (usually) would go along with it.
Looking back at the 10 PPV editions of the event, here's my picks for the best tournament matches. Spoiler: hope you weren't expecting anything from 1999.
10. Bob Holly Vs. The Roadie (Quarter-Final, 1995)
The Roadie won this one but just look at how majestic Bob Holly is there...
Depending on how you feel about Bret Hart and Jerry Lawler's Kiss My Foot match, this quarter-final bout could've been the best match of the 1995 show. Not to disparage the considerable talents of the future Hardcore Holly and Road Dogg, but there's a reason why the 1995 King of the Ring is maligned as one of the worst pay per views of all time.
The match cut a good pace for its seven-and-a-half minute duration, with some early near-falls, although the finish was a bit abrupt. This was supposed to give Roadie one notable victory before his eventual split with Jeff Jarrett (over the whole lip-sync angle), but that didn't exactly go to plan. The Attitude Era just couldn't come fast enough for these two.
9. Ken Shamrock Vs. The Rock (Final, 1998)
In his 16 months with the WWF, Shamrock hadn't been given a truly landmark victory. Sure, he'd had visual submission wins over Shawn Michaels and Bret Hart in the latter part of 1997, but none of that translated into gold. He'd lost two Intercontinental title matches to The Rock via reverse decision, because of the corner WWF painted themselves into: they wanted to keep the belt on Rock, but they didn't want Shamrock to lose his unbeatable aura.
The King of the Ring finals provided a great solution, by allowing Shamrock to cleanly beat Rock with the title switching. Selling a leg injury from his semi-final against Jeff Jarrett, Shamrock traded some dramatic near falls with Rock in the closing moments before winning with his ankle lock. The match is also notable for guest commentator Triple H's errant "lingual" comment: "There's a lot of 'bi' things I am but lingual's not one of them."
8. Chris Jericho Vs. Kurt Angle (Quarter-Final, 2000)
The 2000 tournament might go down as one of the greater disappointments in WWE history, given the talent involved. A bracket that included these two men, along with Chris Benoit, Eddie Guerrero, and Val Venis, was understandably constrained by time, though the show still fell short of high expectations. The Jericho/Angle match makes the cut, while Venis and Guerrero's quarter-final just misses.
As for this match, it's about 10 minutes of what you'd expect from Angle and Jericho in their athletic primes, with all of their big spots plus nifty counters. Being that this is 2000, there's also a screwy finish involving Stephanie McMahon, but what can you do? Matches *without* screwjobs were the real swerves in 2000. Sadly, after Angle's win in this pretty good match, the rest of the night could not equal or surpass this level of quality.
7. Mankind Vs. Triple H (Final, 1997)
This was one of those instances where the crowd reaction just didn't equal the quality of work inside the ring (See: Benoit vs. Malenko, Hog Wild 1996). With 'boring' chants early on, as well as general silence for much of the early portion of the match, the crowd wasn't buying into a freshly-babyface Mankind, nor Helmsley in what would turn into his true launching push.
Mick Foley bumped like a madman in the latter portion of the match, enduring shots into the guardrail, ring steps, and was even Pedigreed through the commentary table. For 1997, this was excessive by WWF's standards, but the goal was to make two new stars: indestructible Mankind, and win-at-all-costs Helmsley. Triple H got the win that he was to have had one year earlier, as there was no 1997 "Curtain Call" to derail plans this time.
6. Rob Van Dam Vs. Chris Jericho (Semi-Final, 2002)
This match spurred a heated online tirade on the part of Jericho, who was disappointed to find that fans didn't particularly care for the bout. In his spiel, Jericho noted that fans who didn't like the match should, "...stop watching the WWE and take up bowling.” Though Jericho's subjective claim that the bout was "match of the year calibre" was a bit of a stretch, it was still easily the best match of a lacklustre pay per view.
The match began slowly, but eventually built to a very good one with Van Dam winning via his Five Star. The fans in Columbus were going nuts for the near falls at the end, so it's hard to say where the criticism really lies, outside of the steady opening portion.
5. Bret Hart Vs. Razor Ramon (Quarter-Final, 1993)
If you're allergic to the Hart Family for some reason, you may wanna steer clear of the rest of this list, because it's just laden with pink and black. According to Bret, he was told that for his three tournament wins that night, he wasn't to win with the Sharpshooter in any of them. This gave Bret the challenge of coming up with creative ways of achieving victory, beginning with "The Bad Guy."
The fact that Hart was working with an ankle injury sustained at Madison Square Garden the night before (he was noticeably limping during his entrance here) makes his performances all the more impressive. For the first unconventional Bret finish, he pinned Ramon after countering a backward Superplex into a pinning combo. To take the Sharpshooter out of the equation, Bret had Razor attack his fingers during the match, giving him another obstructive hill to climb as the night wore on.
4. 123 Kid Vs. Owen Hart (Semi-Final, 1994)
Around the same time frame, there was a match in ECW between Mike Awesome and J.T. Smith that Joey Styles often referred to as, "the damnedest two-minute match you'll ever see." The WWF put out something similar with this tournament match that lasted only three minutes and 37 seconds. For such an abbreviated time frame, Owen Hart and the 123 Kid made you want to see future battles between the two of them, and would've been match of the night if not for Bret Hart vs. Diesel.
The action was frenetic and hot, and the two marvels wedged a lot of eye-catching moves into such a tight window. Hart won clean with the Sharpshooter en route to the crown, finishing off the best sub-five minute WWE pay per view match until perhaps Goldberg vs. Brock Lesnar at WrestleMania 33.
3. Marc Mero vs. Stone Cold Steve Austin (Semi-Final, 1996)
This idea has been put forth that without the Johnny B. Badd gimmick that Marc Mero was totally useless, that he didn't know how to work a match without that gimmick. I disagree with that sentiment wholeheartedly, and use matches like this one as evidence to the contrary. Mero's 1996 was filled with high-quality matches, with this tournament bout standing out the most.
The most notable occurrence in this match (aside from it being Austin's first time doing the Stunner on pay per view) was when Mero accidentally busted open Stone Cold's mouth one a Double Leg Cradle gone wrong. Austin actually had to go to the hospital between this match and the final, but not before he and Mero delivered an entertaining back-and-forth with the emphatic Stunner finish.
2. Bret Hart Vs. Bam Bam Bigelow (Final, 1993)
Counting a 32-minute match that he'd wrestled with Bob Backlund in New York one night earlier (accounting for Hart's ankle injury), Bret had wrestled for 62 minutes in 24 hours. He was now counted on to go out with Bigelow and deliver a scintillating finale that would properly cap off the night's action. In true Hitman fashion, Hart didn't disappoint.
Hart and Bigelow had their share of quality matches together throughout early 1993, cat-and-mouse games that saw the zippier Hart try to outmanoeuvre the burly, yet freakishly agile, "Beast From the East". There was actually a false finish here, as Bigelow won after interference from Luna Vachon, only for the match to be restarted. Hart won with the victory roll after 18 elapsed minutes, which amounted to one hour and 20 minutes worked over the previous day.
1. Bret Hart Vs. Mr Perfect (Semi-Final, 1993)
When one thinks of the best matches that Hart and Perfect have had with one another, usually SummerSlam 1991 immediately comes to mind. While that was indeed an excellent showing, this tournament match was just a hair or two better. The battle of mutually-respecting babyfaces brilliantly degenerated into a hyper-competitive battle of wills, a combination of wrestling match and schoolyard scrum.
You know you're watching a classic when it's two good guys exchanging blows, and heel Bobby Heenan has to remark about what a helluva match it is. The two sold injuries and aches, fought tooth and nail, and Hart barely eked out the victory by reversing an Inside Cradle into one of his own. This may even be the best King of the Ring pay per view match ever, tournament or non-tournament, Hell in a Cell be damned.