The Undertaker is a legend in WWE, a superstar since the day he made his début at the Survivor Series in 1990. Despite that, Undertaker was known for his character and not for great matches through the first decade of his career. His WrestleMania winning streak was the stuff of legend, but matches against an over-the-hill Superfly Jimmy Snuka and immobile Giant Gonzalez defined the early stages of his career.
However, when the Attitude Era arrived, things started to change. Undertaker started turning in solid-to-great matches, only getting better with age. Later in his career, he delivered some of the best matches in WWE history. With his time in the ring seeming to slow to an end, here is a look at some of Undertaker's career highlights.
10 Vs. CM Punk (WrestleMania XXIX)
CM Punk never worked the main event at a WrestleMania in his hugely successful WWE career. Nevertheless, his WrestleMania XXIX match with Undertaker was as close to a main event match as you'll get outside of going on last. Punk delivered a great lead-in, stealing Undertaker's urn and mocking his opponent up until they faced off.
CM Punk was promising to end Undertaker's 20-0 WrestleMania undefeated streak. The match went 22 minutes and saw Punk almost win, but his mocking of Undertaker's "Rest in Peace" pinfall cover cost him and Undertaker eventually won, boosting his record to 21-0 after the match.
9 Vs. Kurt Angle And The Rock (Vengeance 2002)
In 2002, at a minor PPV called Vengeance, Undertaker took part in one of the most exciting matches of his career. There was little build-up to this match and it wasn't considered a major moment at the time, but the contrast in styles between the three wrestlers involved created something very special.
Undertaker, with his brawling offense, came in as the champion, while The Rock was an electrifying performer and Kurt Angle was possibly the best pure wrestler in the company. The Rock ended up winning by pinning Angle as Undertaker missed the breakup at the last possible second. This was Rock's final title reign before leaving for Hollywood.
8 Vs. Kurt Angle (No Way Out 2006)
Four years after Kurt Angle was pinned at Vengeance to cost Undertaker the WWE title, the two battled in a singles match at a WWE PPV called No Way Out in 2006. This was a fantastic match, with Angle as the accomplished wrestler and Undertaker as the big man willing to do anything to win.
The match was similar to many of Undertaker's later career matches: relentless and exciting. This was not a WrestleMania match, but it stands up to almost any Undertaker WrestleMania match until the last decade of action. Angle won the match, giving Undertaker a rare pinfall loss.
7 Vs. Triple H (WrestleMania XXVII)
After Undertaker and Shawn Michaels had back-to-back WrestleMania matches that were among the best of all time, there was little chance Undertaker could replicate that success. With that said, Triple H wanted to not only give it a try but have back-to-back WrestleMania matches against the Dead Man as well.
The second was in a Hell in a Cell with Shawn Michaels as the guest referee, but the better of the two was the first one at WrestleMania XXVII. Before the streak ended against Brock Lesnar, this was the one match where it really looked like he was going to lose. Still, he held on and beat The Game in a fantastic WrestleMania match.
6 Vs. Kane (WrestleMania XIV)
Undertaker has had a lot of rivalries over his career, with everyone from Shawn Michaels and Triple H to Mankind and Stone Cold Steve Austin. However, if there's one rival that defines the career of Undertaker, it's Kane.
Kane was introduced as Undertaker's brother, a love-hate sibling relationship that would last their entire respective careers. When it comes to the matches they fought against each other, their battle at WrestleMania XIV sits at the top of the mountain. This was their first match after Kane's début and it took three Tombstone Piledrivers for Undertaker to eventually win.
5 Vs. Shawn Michaels (WrestleMania XXVI)
Undertaker vs. Shawn Michaels remains one of the greatest WrestleMania matches of all time. They fought twice, but it was the first bout that sits at the top of most lists. However, that does not take anything away from their second match: the one where Undertaker beat Shawn Michaels and caused his retirement from professional wrestling.
WrestleMania XXVI was all about the Streak vs. the Career and it was Undertaker who took the win, ending the career of the Heartbreak Kid. The significance of ending the career of one of the best of all-time did nothing to overshadow how perfectly set up this match was. It remains one of the best ever.
4 Vs. Edge (WrestleMania XXIV)
It is easy to forget how great Edge was as a heel in WWE. He was, in his day, the most hated man in professional wrestling, because of how great he was at drawing the right kind of heat. The fact that he had not one, not two, but three amazing matches against Undertaker shows that he had the respect of the Dead Man as well.
Undertaker beat Edge at SummerSlam in 2008, choke-slamming him through the ring after the match. He then beat him again at One Night Stand in 2008. However, it was their match at WrestleMania XXIV --during which Edge was the world champion and it actually looked like he had a chance to end the streak-- that remains the best match the two men fought against each other.
3 Vs. Shawn Michaels (Badd Blood 1997)
Yes, there are three different matches on this list between Undertaker and Shawn Michaels. Two of them are the back-to-back WrestleMania matches, which ended with the Heartbreak Kid retiring from WWE. However, this one came 12 years before the first of those two matches. It took place at a minor WWE PPV from the In Your House series called Badd Blood.
The match remains known for an ending that saw neither man win cleanly, but introduced Kane to the world for the first time (as he came down and attacked his brother while Shawn Michaels escaped the cage). However, this was the first ever Hell in a Cell match --something Undertaker became known for -- and remains one of the best of its kind.
2 Vs. Mankind (King Of The Ring 1998)
The King of the Ring 1998 Hell in a Cell match remains known for the most famous moment in WWE history. Forget about Hulk Hogan slamming Andre the Giant, or Shawn Michaels achieving his boyhood dream after a 60 minute Iron Man match. The moment when Undertaker threw Mankind off the top of the Cell and through a table is a moment that people still talk about to this day.
While other people have replicated the move, it just wasn't as significant as it was in this match. The fact that Mick Foley got up, climbed to the top again and was choke-slammed through the roof of the cage to the ring --legitimately knocking himself out-- only adds to the legacy of this match.
1 Vs. Shawn Michaels (WrestleMania XXV)
The greatest match of Undertaker's career, and possibly the best WWE match of all-time, came at WrestleMania XXV. There was nothing on the line but Undertaker's streak and Shawn's pride in this one. Despite that, the two men worked a perfect match.
It was the "light" of Shawn Michaels vs. the "darkness" of Undertaker, the big man against the smaller athletic high-flyer. Shawn always delivered at WrestleMania and Undertaker had never lost there. These two men had WWE fans eating out of their hands and delivered the best match any WWE fan had ever witnessed in the company.