The biggest event of the WWE calendar is WrestleMania. Every storyline, angle, feud, what-have-you builds throughout the year and culminates at what they’ve dubbed “the grandest stage of them all,” and “the showcase of the immortals.”

Two words have become synonymous with WrestleMania over the last several years: The Streak. The Undertaker, who competed in his first WrestleMania in 1991, has participated in more WrestleMania matches than anybody in history. What’s even more impressive that that statistic is the fact that he has never lost a WrestleMania contest. With his most-recent victory over Triple H earlier this year, he went to 20-0 on the big stage.

With that marketable number in mind, WWE saw fit to release a four-disc retrospective chronicling the Undertaker’s WrestleMania history. Released last month, the first disc features a documentary looking at all 20 matches, featuring comments from WWE personalities and opponents. Since Undertaker is one of the few characters who still abides by the old-time tradition of “kayfabe” (not breaking character, acting like it’s real), the hour-long documentary features in-character comments and looks at each match in that manner.

With Undertaker having such a long history and WWE marketing toward a much-younger audience these days, disc 1 is a good piece for fans who may not know the full history. It’s a good educational piece for casual wrestling fans or young children. It honestly didn’t hold my interest, since I knew about the streak already.

Discs 2, 3 and 4 are where the set becomes worth the money, as all 20 matches are featured in their entirety. The last four years, The Undertaker has been involved in match of the year contenders. The four-year story arc involving Undertaker ending Shawn Michaels career and dealing with Triple H after that has been a thing of beauty. It would have been an amazing six-month feud, had it not been stretched out for four years over WrestleMania season, so to speak.

The thing that WWE has tried to gloss over lately is the fact that The Streak was not something that has been in the works for the last 20 years. Like Jim Ross has mentioned in his blog before, nobody decided to create the streak. Around 8-0, they noticed he was undefeated and mentioned it. Undertaker first mentioned it at 10-0 (he counted to 10 on his fingers after the match). The words “The Streak” were not mentioned until Randy Orton in 2005. And, to be honest, some of those early matches were pretty bad, with his match against Giant Gonzalez being among Undertaker’s worst of his career.

But, if you’re a fan of wrestling, and more specifically, The Undertaker, this set is a must-own. It’s a collection of history, something we will likely never see again.

With this post, we’ll take a look at Undertaker’s 20 matches, ranking them from worst to best. The ranking system includes quality of the match, historical significance, and my biased opinion as a fan. If you agree or think I have no idea what I’m talking about, let me know.

Here we go:

20) Undertaker vs. Giant Gonzalez (1993) … Jorge Gonzalez was a legit 7’6” former basketball player. He was drafted to the Atlanta Hawks and was not NBA quality. Ted Turner owned both the Hawks and WCW, so Gonzalez became a wrestler. He had an entertaining feud with Ric Flair, but after going to WWE, could not replicate that success with Undertaker, who was not at the stage of his career where he could carry a greener wrestler to a good match. They stood there and hit each other a lot. Gonzalez got disqualified, giving Undertaker his only win not by pinfall or submission. Scary to think that Undertaker could have possibly lost here, as the match was really used to get over Gonzalez to continue their feud.

19) Undertaker vs. Jimmy Snuka (1991) … The first match in the streak. Snuka had been one of the top stars during the early 1980s and this match was seen as a passing of the torch. The aging veteran was easily dispatched by this newcomer who had debuted only 5 months earlier.

18) Undertaker vs. King Kong Bundy (1995) … Undertaker was involved in a feud with Ted DiBiase’s “Million Dollar Corporation” and this match continued that. DiBiase had stolen Undertaker’s urn and Undertaker tried to get it back. He succeeded in the match, but Kama (aka The Godfather) stole it back and melted it down into a necklace. Dumb storyline, but that’s what they did back then. Match was nothing special. The MLB was on strike at the time and a baseball umpire was the referee for the match, as a way to try and get some media attention.

17) Undertaker vs. Diesel (1996) … Kevin Nash’s last WrestleMania before he went to WCW. The match was slow and plodding, with Diesel trying to wear Undertaker down with multiple bear hugs. The crowd was still into it big time, though.

16) Undertaker vs. Big Boss Man (1999) … The first Hell in a Cell match in WM history. Also generally considered one of the worst HIAC matches in history. At the time of its release, this was the only match not included in the HIAC compilation 3-disc set. Boss Man handcuffed Undertaker to the cell and that looked to play a major role in the match, but then the cuff broke within a few minutes and it looks like they had to scramble with a plan B. It didn’t work.

15) Undertaker vs. Big Show and Albert (2003) … Originally supposed to be a tag match with Nathan Jones. WWE reportedly didn’t think the newcomer was ready for a WM match, so they staged a beat down that took him out of action. Action was fast-paced due to Undertaker trying to maintain the advantage over two larger opponents. Match was during the end of his “American Badass” phase, so he got a huge pop for breaking the Tombstone piledriver out, a move he rarely used then. WM19 occurred mere weeks into the US/Iraq war, so one of the biggest pops of the night occurred when Undertaker came to the ring with an American flag.

14) Undertaker vs. Mark Henry (2006) … The only casket match in WM history. Entertaining match, especially considering Henry’s limitations. Mostly remembered for Undertaker’s plancha over the top rope and over the casket, landing on top of Henry. A couple years later, Monday Night Raw hyped several WrestleMania rematches throughout the night and this one was contested again. The outcome was the same. Undertaker is 2-0 against Mark Henry in casket matches.

13) Undertaker vs. Psycho Sid (1997) … Undertaker’s second WWE Championship victory, and first at WM. Sid had his working shoes on that night, as he moved quicker than usual and also came off the top rope several times (I cringed each time, as it conjured up memories of his gruesome 2001 injury). Bret Hart, getting his new heel character over, interfered 3 times in the match. Shawn Michaels, fresh off his “knee injury” and “losing his smile” is on guest commentary. He was full of inside snark and shoot comments that only he could get away with.

12) Undertaker vs. Jake Roberts (1992) … Jake Roberts had turned heel the previous year and had formed a partnership with the equally evil Undertaker. That all changed when Roberts was going to hit Ms. Elizabeth with a chair. Undertaker finally grew a heart and stopped Roberts. This was Roberts’ last match in WWE until 1996. In his WWE DVD documentary, Roberts talks at length about why. Very fascinating backstage politics at work.

11) Undertaker vs. Kane (2004) … Undertaker’s first WM rematch, as he previously faced Kane in 1998. This was the re-debut of Undertaker as “The Deadman,” as Kane had helped Mr. McMahon defeat Undertaker in a “Buried Alive” match at Survivor Series 2003. He buried Undertaker and effectively “killed him,” so Undertaker was now back to being dead and tormenting Kane. Match was somewhat brief, but the introduction for Undertaker was off-the-charts awesome.

10) Undertaker vs. Randy Orton (2005) … Orton had been WWE’s top heel under Triple H. He then usurped HHH as top bad guy, only to have H turn on him. Orton’s run as top face was a bust, so to set his heel turn into action, he decided that he would end The Streak to make a name for himself. It didn’t work. Orton’s father, “Cowboy” Bob Orton was being inducted into the WWE Hall of Fame that year and made a cameo appearance with his cast to try and help his son. It didn’t work.

9) Undertaker vs. Triple H (2010) … Undertaker had ended Shawn Michaels’ career and Triple H was out for revenge. This match was nonstop action, with heavy hands, hard falls, and an unprotected chair shot to the head or two (which WWE issued a press release for saying that the two had been fined for). The ending was drama personified, as Undertaker won the match but did not leave the ring under his own power, as he was too exhausted and beat up.

8) Undertaker vs. Kane (1998) … Paul Bearer had tormented Undertaker for months, promising to unleash Undertaker’s long-thought-dead brother on him. Kane made his WWE debut in Sept. 1997 and tried to goad Undertaker into a match from that point on. Undertaker resisted until March, which coincidentally set their first encounter for WrestleMania 14 (best known for Steve Austin’s first WWE Championship victory). Undertaker took a nasty fall through the Spanish announce table, but ultimately vanquished Kane after three Tombstone piledrivers.

7) Undertaker vs. Batista (2007) … Undertaker had won the Royal Rumble earlier that year, last eliminating Shawn Michaels. He earned a shot at the title of his choosing and went after Batista. With two title matches that year, Batista vs. Undertaker for the World Championship and Cena vs. HBK for the WWE Championship, only one match could be in the main event. WWE put Batista and Undertaker on in the middle. They stole the show. Batista wrote in his autobiography that he received some heat for coming back after the match and yelling “Follow that!”

6) Undertaker vs. Edge (2008) … Interesting dynamic here, as Undertaker had never lost a match, while Edge could make the claim that he had never been pinned at WrestleMania (as he had lost a ladder match the previous year). He could still make that claim, as Undertaker made him submit to the “Hell’s Gate” gogoplata MMA maneuver.

5) Undertaker vs. Triple H (2012) … Billed as the “End of an Era,” these two part-time warriors competed in Hell in a Cell match with Shawn Michaels as the guest referee. Undertaker was battling injuries and this was only his second match in the previous 15 months. Triple H was slowing down his ring work to focus more on backstage duties. He had only wrestled a handful of times the previous year. HBK had been retired for two years and shown up only a couple times since. They told a great story of Triple H being jealous of Michaels, trying to do the one thing he could never do – end the streak. The question of whether Michaels would call it down the middle or try to end the streak as a referee was an added wrinkle. In the end, Undertaker prevailed and all three walked up the ramp together, having earned each others respect.

4) Undertaker vs. Ric Flair (2002) … In Flair’s autobiography, he wrote that this match was what brought him out of his funk, brought on by his own insecurities over his place in wrestling at his age. He and Undertaker had an intense, hard-hitting match. Flair was in top form here and Undertaker was at his vicious best, having recently turned heel. A run-in by Flair’s Four Horsemen “Enforcer” from the good ol’ days, Arn Anderson, wasn’t enough to end The Streak. Undertaker finished off Flair with a Tombstone to go 10-0.

3) Undertaker vs. Shawn Michaels (2010) … The last match of HBK’s storied career. The year before, he had attempted to end the streak. He wanted a rematch. Undertaker said yes, with the condition that he put his career on the line. Michaels said that if he couldn’t get the job done, he had no career. Given the main event slot over the WWE and World title matches, these two told a story like only they can do. Michaels tried to chop down the big man and Undertaker kept coming back for more. Undertaker started to show mercy at the end, only to be disrespected by HBK with a slap across the face. He hoisted Michaels up and with a leaping Tombstone piledriver, ended the career of one of the all-time greats.

2) Undertaker vs. Triple H (2001) … Earlier, we talked about end of an era with these two. WrestleMania 17 is unofficially considered the end of the “Attitude Era,” and these two were key figures in it. Triple H admitted he had done everything in WWE with the exception of defeat the Undertaker. The battle was on. And what a battle it was. Triple H was nearing his prime and Undertaker was looking good, having found his groove with the “American Badass” character. They brawled throughout the ring and into the crowd, with Undertaker finally getting the victory with his “Last Ride” power bomb maneuver.

1) Undertaker vs. Shawn Michaels (2009) … The twenty-fifth WrestleMania saw Undertaker and HBK steal the show and have arguably the greatest match in WM history, and no doubt a top 3 encounter. Words hardly do it justice. It’s all about telling a story and the magic that two men can make inside of a 20 x 20 ring. They did it. They crafted a masterpiece that will go down in history. The close calls, the submission attempts, the look of utter shock and exhaustion on Undertaker’s face after HBK kicks out of the Tombstone, they took the crowd on an emotional roller coaster. A must-watch for any fan of professional wrestling.

And there we have it. Twenty matches, in order. But, is it the correct order? If you don’t believe so, let me know. Comments and criticism is encouraged and appreciated.