1990- Not much to say here with his debut coming at the end of the year. The WWF did pretty much the only thing they could do with Taker in the match. They had him dominate until he was counted out. You couldn’t have him win because of the Grand Finale match at the end of the show. Hogan and Warrior weren’t about to job to him and the show was going to end with them winning. It was a strong debut for someone debuting in 1990.
1991- I know Undertaker goes on to win the WWF title at the end of the year in a big moment for him. But I do wish Ultimate Warrior stuck around after SummerSlam that year. The vignettes with Jake Roberts and the Warrior, leading to the reveal that Roberts was working with Taker, were great. I thought the pairing of Roberts and Taker worked well in the short time they were together.
1992- How great is that entrance at SummerSlam? Night had fallen on Wembley Stadium and out comes Taker on the back of a hearse riding to the ring to fight Kamala. Kamala’s sell of fear here and then of the casket at their match at Survivor Series made this storyline fun.
1993- Imagine being stuck feuding with Giant Gonzalez for almost the whole year. Poor Taker had to deal with that immobile giant for so long. That is actually a running theme of what is to come for Taker.
1994- Undertaker, or Marty Jannetty, rising from the video screen up to the rafters of the arena at Royal Rumble 1994 was awesome to watch as a kid and still awesome to watch now. I don’t care how corny it was. I think it is great. And then it lead to Chuck Norris making a WWF appearance later in the year in a rematch with Yokozuna.
1995- As bad as feuding with Giant Gonzalez was in 1993, I think 1995 might have actually been worse. Taker feuded with the Million Dollar Corporation through August. That included matches with the likes of I.R.S., King Kong Bundy and Kama. Then he feuded with King Mabel, who broke Taker’s face with a piss poor leg drop. I mean at least the Giant Gonzalez matches were short. Plus, imagine Mabel sitting on your face.
1996- I would consider this the “turnaround” year of the Undertaker’s career. After disposing of Kevin Nash at Wrestlemania, he goes onto a year long feud with Mankind with multiple good matches. Paul Bearer leaves him for Mankind and it lights a fire under the character of the Undertaker. Plus he had 3 PPV matches with Goldust during this year, which is something I completely forgot about.
1997- If 1996 was the turnaround year, 1997 might have been Taker’s best year. He finally gets back to the top of the WWF by winning the WWF title at Wrestlemania. He has good matches defending against Steve Austin, Mankind, Vader and Bret Hart. Then at the end of the year he has two great matches with Shawn Michaels. Oh, and Kane also debuts setting off that story that would go on for years. 1997 may be the best year of the Undertaker.
1998- The long awaited Kane match was a great spectacle but ended up being a dud from a match perspective. The story went on throughout the year with Stone Cold getting added to the mix, as well as Mankind. By the end of the year Taker was dealing with nagging injuries and it showed in his work. At least we got Austin vs Taker at SummerSlam, and that great Highway to Hell video package.
1999- Ministry of Darkness Undertaker. Fun fact- My friends and I in school at the time (5th grade) formed our own group called the Ministry and always said we were going to sacrifice someone and hang them on a fake Undertaker symbol. Never happened. I liked the Ministry on its own. But then it became the Corporate Ministry and got way too complicated. I was at Fully Loaded 1999, which was my first PPV I attended.
2000- Welcome to the world Biker Taker. The return was great. After that? Ehh not so much. I will always hold it against Taker that he made Kurt Angle look like a jobber in their match at Fully Loaded. The same show Rock and HHH made Chris Benoit and Chris Jericho look like stars. Meanwhile Kurt Angle barely got any offense in. After the debut of Biker Taker things went south fast.
2001- The year started off with a very good match against Triple H at Wrestlemania. I think that match is better than their other two matches. But then the Invasion drags everything down. Taker jobs out DDP, and pretty much does nothing to get over any of the WCW guys. In fairness none of the WWF’s booking did, but Taker in particular seemed to go out of his way to make no one look good.
2002- Taker redeems himself a bit this year. He puts on another great match at Wrestlemania, this time with Ric Flair. Then he has the ladder match with Jeff Hardy that puts Jeff on the map as a possible singles star down the line. This is honestly a year of really good Undertaker matches. On top of those two, he also has his triple threat match at Vengeance against Kurt Angle and The Rock, as well as two matches with Brock Lesnar.
2003- And then we have this year, the complete opposite of 2002. There is nothing memorable about this year at all. Except the fact that Taker gets buried alive, setting up what would come in 2004.
2004- And of course that would be the return of the Deadman Undertaker. I was disappointed in the look when he came out I really wanted him to go back to the gear he had in 1998. But instead he basically looked like Biker Taker but acted like Deadman Taker. Oh yeah, and he buried Paul Bearer alive in cement and killed him off. A much anticipated return ended with a stinker of a year.
2005- The Undertaker had exactly two feuds this year. One was with Muhammed Hassan, which we won’t talk about. The other is with Randy Orton. It was a feud that put Orton back on the right track after his stinker of a run with the World title. Orton himself talked about the respect he had for Taker during this time. It was a redemption feud for Orton, and he has the Undertaker to thank for his career turnaround.
2006- So remember how I said I hated that Undertaker vs Kurt Angle match from Fully Loaded 2000? It is completely the opposite in 2006 with their match at No Way Out. It is seriously awesome and not one brought up enough in the career of both men. Go out of your way to watch this match if you have not seen it.
2007- Here’s something I find a little funny. I feel Undertaker had better matches with Randy Orton than Triple H did. And I would say the same thing about Undertaker and his matches with Batista. Their matches together were much better than the matches of Triple H and Batista. Read out of that what you will.
2008- I feel like enough people don’t talk about Undertaker’s almost year long feud with Edge. I mean they didn’t have a bad match throughout the year. Taker took a freaking huge bump off a ladder through tables outside the ring in a TLC match. The Edge vs Undertaker feud probably wouldn’t end up on either of these men’s top rivalries list, but it should end up on both men’s top matches list.
2009- Undertaker vs Shawn Michaels. Wrestlemania XXV. That is the thought. Is it the greatest Wrestlemania match of all time? I still debate this in my head. My Top 3 are this one, Austin vs Bret at Wrestlemania 13 and Ultimate Warrior vs Randy Savage at Wrestlemania 7.
2010- Yes, twelve years later the WWE went back to the Kane vs Undertaker well. But is was nowhere near as intriguing. And the spectacle of the matches was completely missing. But hey Kane got to bury his brother alive again. I guess if at first you don’t succeed try again right?
2011- I couldn’t be the only person hoping for Sting vs Undertaker this year right? Remember those old Western style vignettes of someone in a dark trench coat outside in the rain? I was convinced they were for Sting and I believe the thought at the time was they were left vague for the possibility of Sting finally signing with the WWE. But instead Sting re-signed with TNA and we got the first of Triple H vs Undertaker at Wrestlemania. This was my first Wrestlemania I attended in person and I was quite disappointed it was not Sting vs Taker.
2012- FORTUNE FAME. That Metallica song was seared into everyone’s heads in the build up to Wrestlemania. I’m still convinced everyone involved in this match was angling for an Academy Award nod with the acting going on in it.
2013- This was the first year I really thought the Undertaker’s opponent should end The Streak. Obviously I wanted Shawn Michaels to end it at Wrestlemania 26 since I didn’t want him to retire. But I knew that wouldn’t help anyone in the end. I thought CM Punk ending the Streak would make him an even bigger star than his 434 day title reign did.
2014- Brock Lesnar should not have ended The Streak. And in hindsight, we can tell that Lesnar ending The Streak did nothing for anyone. It was an awful decision that left everyone at my Wrestlemania party that year stunned, including all of my non-wrestling fans.
2015- The Bray Wyatt feud was really awful. I hated that Taker did not show up in the build to this feud at all. Imagine if Taker won last year and Bray was the one to break The Streak this year?
2016- Imagine wasting one of The Undertaker’s last Wrestlemania matches on Shane McMahon?
2017- The Roman Reigns match at Wrestlemania was really tough to watch. I remember watching it as it happened and just cringing at everything that went on. I felt awful for Taker. I thought it was a clear sign he should have hung up the boots. Also imagine if heel Roman now beat The Undertaker to end The Streak?
2018- Imagine doing a John Cena vs Undertaker match at Wrestlemania, one of the last big matches left you can do, with the thought Taker might not show up. Then imagine doing a 5 minute match between the two.
2019- I was at this year’s Wrestlemania with a friend whose favorite wrestler was The Undertaker. I felt awful for him when Taker was not on the show. But at least he was on RAW so he got to see him there.
2020- The Boneyard match was great and a nice little send off for Taker.