{"id":225161,"date":"2026-11-13T12:12:27","date_gmt":"2026-11-13T18:12:27","guid":{"rendered":"https:\/\/www.pwtorch.com\/site\/?p=225161"},"modified":"2026-11-13T12:12:27","modified_gmt":"2026-11-13T18:12:27","slug":"then-now-forever-the-undertaker-edition-the-evolution-of-the-undertaker-which-was-introduced-36-years-ago-this-month-with-a-look-at-key-matches-with-bret-hart-kurt-angle-shane-mcmahon","status":"publish","type":"post","link":"https:\/\/www.pwtorch.com\/site\/2026\/11\/13\/then-now-forever-the-undertaker-edition-the-evolution-of-the-undertaker-which-was-introduced-36-years-ago-this-month-with-a-look-at-key-matches-with-bret-hart-kurt-angle-shane-mcmahon\/","title":{"rendered":"THEN, NOW, FOREVER &#8211; THE UNDERTAKER EDITION: The evolution of the Undertaker which was introduced 36 years ago this month with a look at key matches with Bret Hart, Kurt Angle, Shane McMahon"},"content":{"rendered":"<div id=\"pwtor-2140140844\" class=\"pwtor-before-content pwtor-entity-placement\" role=\"region\" aria-label=\"Advertisements\"><hr \/><b>SPOTLIGHTED PODCAST ALERT (YOUR ARTICLE BEGINS A FEW INCHES DOWN)... <\/b>\r\n\r\n<iframe src=\"https:\/\/widget.spreaker.com\/player?show_id=3076978&theme=light&playlist=false&playlist-continuous=false&autoplay=false&live-autoplay=false&chapters-image=true&episode_image_position=right&hide-logo=false&hide-likes=false&hide-comments=false&hide-sharing=false&hide-download=true\" width=\"100%\" height=\"140px\" frameborder=\"0\"><\/iframe>\r\n<hr \/><\/div><p>In November 1990, nearly 36 years ago, The Undertaker made his debut at Survivor Series. From his initial introduction, the uniqueness of the character immediately captured attention and created an undeniable mystique. His distinct look, imposing stature, ominous movements, and haunting funeral procession music made him stand out from everyone else.<\/p>\n<p>With that said, when the character was first introduced, it&#8217;s hard to imagine anyone predicting that he would last more than three decades, let alone forge a legacy that would be remembered and beloved by generations of wrestling fans.<\/p>\n<p>So, why did it work? I think evolution is the simple answer. Sometimes that evolution came through small cosmetic changes, such as accent colors, ring gear, or hairstyles. On other occasions, it involved a complete overhaul of the character, most notably the American Badass version of The Undertaker.<\/p>\n<p>In addition to his evolution as a character, his development as a professional wrestler was equally remarkable. Initially, his wrestling style relied heavily on character and atmosphere, with relatively little emphasis on athletic action. He operated almost like a living zombie. As the years progressed, however, The Undertaker gradually downplayed the supernatural aspects of the Deadman character and developed into an outstanding professional wrestler. He showcased phenomenal striking ability and tremendous mobility for someone approaching seven feet tall.<\/p>\n<p>This evolution was largely complete by the mid-2000s, when The Undertaker had become not only an iconic character but also a performer capable of delivering some of the greatest matches in professional wrestling history.<\/p>\n<p>In this week&#8217;s article, I&#8217;ll highlight three matches from The Undertaker&#8217;s long and storied career, examining the qualities that made him a phenom, not just in name, but in reality.<\/p>\n<hr \/>\n<h3>Then: Bret Hat vs. The Undertaker: (WWF Madison Square Garden: January 31, 1992)<\/h3>\n<p>I didn&#8217;t care at the time, nor did I really notice, but the first few years of The Undertaker&#8217;s WWF career featured some incredibly slow and, at times, boring matches. After all, watching a zombie in action isn&#8217;t quite as exciting as an episode of The Walking Dead makes it look. In those early years, living and performing the gimmick was much more important than the quality of the in-ring action.<\/p>\n<p>With that said, even during the first few years of The Undertaker&#8217;s WWF run, we saw glimpses of the athleticism and fleet-footed big-man style that he would continue to develop in the late &#8217;90s and ultimately perfect in the 2000s.<\/p><div id=\"pwtor-2880639805\" class=\"pwtor-content pwtor-entity-placement\" role=\"region\" aria-label=\"Advertisements\"><div align=\"center\" data-freestar-ad=\"__336x280 __336x280\" id=\"pwtorchcom_test_300x250\">\r\n  <script data-cfasync=\"false\" type=\"text\/javascript\">\r\n    freestar.config.enabled_slots.push({ placementName: \"pwtorchcom_test_300x250\", slotId: \"pwtorchcom_test_300x250\" });\r\n  <\/script>\r\n<\/div><\/div>\n<p>This 1992 Madison Square Garden match against Bret Hart is a good example. We get the zombie-like performance that defined the initial version of The Undertaker, but we also see flashes of the athletic big man who would eventually earn the respect of generations of wrestling fans.<\/p>\n<p>In the early stages of the match, we see the methodical, zombie-like prowling of The Undertaker. However, every time Bret goes on offense and the match features rope-to-rope action, you notice just how quick and mobile The Undertaker could be. These sequences provide some of the match&#8217;s biggest highlights, and you can feel the crowd&#8217;s energy come alive.<\/p>\n<p>We also get a glimpse of The Undertaker&#8217;s ability to take maneuvers and sell in his own unique fashion. In the later stages of the match, Bret goes on offense with his trademark moves, including the Russian leg sweep and backbreaker. The Undertaker is able to get up for Bret and allow him to shine, showing an early understanding of how to work with a smaller opponent.<\/p>\n<p>While the finish is rather lame, this night at Madison Square Garden gave us an early glimpse of what would eventually make The Undertaker one of the greatest big men in professional wrestling history.<\/p>\n<p><a href=\"https:\/\/www.youtube.com\/watch?v=4J78TcnBh0s\">CLICK TO WATCH<\/a><\/p>\n<p><iframe loading=\"lazy\" title=\"FULL MATCH: Undertaker vs. Bret Hart: Madison Square Garden, Jan. 31, 1992\" width=\"500\" height=\"281\" src=\"https:\/\/www.youtube.com\/embed\/4J78TcnBh0s?feature=oembed\" frameborder=\"0\" allow=\"accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture; web-share\" referrerpolicy=\"strict-origin-when-cross-origin\" allowfullscreen><\/iframe><\/p>\n<hr \/>\n<h3>Now: The Undertaker &amp; Roman Reigns vs. Shane McMahon &amp; Drew McIntyre (WWE Extreme Rules: July 14, 2019)<\/h3>\n<p>Following the end of the streak at WrestleMania 30, the final years of The Undertaker&#8217;s career were nerve-racking to watch as a fan. On some occasions, against the likes of Goldberg, Roman Reigns, and Shane McMahon, he looked frail and immobile, a shadow of his former self. During these performances, there was a legitimate fear that The Undertaker was doing damage to both his legacy and his health.<\/p>\n<p>On other occasions, however, The Undertaker looked like The Undertaker. He played the hits, executing his trademark spots and mannerisms with precision. His redemption matches against Brock Lesnar were good examples of this.<\/p>\n<p>While his final wrestling appearance in the Boneyard Match at WrestleMania 36 was a fitting end to his career, one of his most overlooked late-career performances came at the Extreme Rules 2019 pay-per-view, where he teamed with Roman Reigns against Shane McMahon and Drew McIntyre.<\/p><div id=\"pwtor-2611526836\" class=\"pwtor-content-1 pwtor-entity-placement\" role=\"region\" aria-label=\"Advertisements\"><!-- Tag ID: pwtorchcom_test_300x600 -->\r\n<div align=\"center\" data-freestar-ad=\"__336x280 __300x600\" id=\"pwtorchcom_test_300x600\">\r\n  <script data-cfasync=\"false\" type=\"text\/javascript\">\r\n    freestar.config.enabled_slots.push({ placementName: \"pwtorchcom_test_300x600\", slotId: \"pwtorchcom_test_300x600\" });\r\n  <\/script>\r\n<\/div><\/div>\n<p>The tag-team format allowed The Undertaker to shine in small doses while giving the audience time to anticipate his entrance into the ring and the execution of his trademark moves and mannerisms. The other three competitors played their roles exceptionally well, creating movement, building anticipation, and allowing The Undertaker to shine.<\/p>\n<p><em>ARTICLE CONTINUED BELOW&#8230;<\/em><\/p>\n<hr \/>\n<h3>Check out the latest episode of &#8220;Worse or Better&#8221; with Josh White, part of the PWTorch Dailycast line-up: <a href=\"https:\/\/www.spreaker.com\/episode\/worse-or-better-the-osha-has-no-memory-lansdell-white-take-a-look-at-wrestler-health-wellness-and-safety-throughout-the-years--76273592\">CLICK HERE<\/a> to stream (or search \u201cpwtorch\u201d on Spotify, Apple Podcasts, or any other iOS or Android app to subscribe free)<\/h3>\n<p><iframe loading=\"lazy\" title=\"Worse or Better (The OSHA Has No Memory) - Lansdell &amp; White take a look at wrestler health, wellness, and safety throughout the years\" src=\"https:\/\/widget.spreaker.com\/player?episode_id=76273592&amp;theme=light&amp;playlist=false&amp;playlist-continuous=false&amp;chapters-image=true&amp;episode_image_position=right&amp;hide-logo=false&amp;hide-likes=false&amp;hide-comments=false&amp;hide-sharing=false&amp;hide-download=true\" width=\"100%\" height=\"200px\" frameborder=\"0\" data-mce-fragment=\"1\"><\/iframe><\/p>\n<hr \/>\n<p>In the early stages of the contest, Taker looks nimble and motivated. Both Drew and Shane do a phenomenal job of moving into position and selling, using their facial expressions and physical bump-taking to make The Undertaker&#8217;s offense look impactful.<\/p>\n<p>The final stages of the match are particularly effective. As the action breaks down and Elias appears to give the heel team a numbers advantage, Shane executes two of his trademark high spots: the elbow drop through the announce table and the Coast to Coast dropkick, which incapacitate The Undertaker. With Roman Reigns also taken out on the floor after a Claymore Kick, it appears the heel team is going to prevail.<\/p>\n<p>But then we get the trademark Undertaker moment. Rising from the dead, he sits up and stares a hole through Shane McMahon. Taker delivers a Chokeslam and sets up for the Tombstone. Drew attempts to prevent the deathblow, but he&#8217;s intercepted by a Roman Reigns spear that comes flying into the frame out of nowhere. This allows Taker to deliver his famed Tombstone and secure the victory, much to the delight of the Philadelphia crowd.<\/p>\n<p>This was one of the final great showings from The Undertaker, and it highlighted all the classic Undertaker spots that fans had come to love. Moreover, because of the match format and the other talent in the ring, Taker was able to play the hits in tune and on key while hiding some of the weaknesses and shortcomings that naturally come with being a weathered and aging competitor.<\/p>\n<p>On this night, the fans got an Undertaker who did justice to his persona and aura.<\/p>\n<p><a href=\"https:\/\/www.youtube.com\/watch?v=waqG2iDkWo0&amp;list=WL&amp;index=6&amp;t=1688s\">CLICK TO WATCH<\/a><\/p>\n<p><iframe loading=\"lazy\" title=\"FULL MATCH: Undertaker &amp; Roman Reigns vs. Drew McIntyre &amp; Shane McMahon: WWE Extreme Rules 2019\" width=\"500\" height=\"281\" src=\"https:\/\/www.youtube.com\/embed\/waqG2iDkWo0?start=1688&amp;feature=oembed\" frameborder=\"0\" allow=\"accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture; web-share\" referrerpolicy=\"strict-origin-when-cross-origin\" allowfullscreen><\/iframe><\/p>\n<hr \/>\n<h3>Forever: Kurt Angle vs. The Undertaker (WWE No Way Out: February 19, 2006)<\/h3>\n<p>When discussing The Undertaker\u2019s greatest matches, it\u2019s easy to choose from the catalog of his WrestleMania streak. After all, his matches against the likes of Edge, Batista, CM Punk, Triple H, and Shawn Michaels are among the best of his career. However, in my opinion, The Undertaker\u2019s best match was against Kurt Angle at the No Way Out pay-per-view in 2006.<\/p>\n<p>By this point, The Undertaker had already proven that he was more than capable of having a great and exciting wrestling match, but this contest took things to another level. When I think about the attributes that made The Undertaker special, I can point to several. He was an excellent striker, developed a technically sound submission game for a big man, possessed fantastic rope-to-rope and corner-to-corner mobility, and later in his career became a tremendous big-man seller. All of these qualities are on display in his match against Kurt Angle.<\/p>\n<p>In the early stages of the bout and again during the closing sequences, The Undertaker demonstrates his mechanical ability to move in and out of holds in a manner rarely seen from a big man. Throughout the contest, he also showcases his tremendous selling ability. It\u2019s difficult for a big man, especially one with the aura of The Undertaker, to sell convincingly without undercutting his persona. However, Taker figured out how to do this effectively in the later stages of his career. He sells the pain while constantly fighting back, never coming across as weak or physically inferior. In this match, Kurt Angle is the perfect aggressive competitor to bring out that aspect of Taker\u2019s performance.<\/p>\n<p>Another fantastic component of this match, which makes the closing stages absolutely white-hot, is The Undertaker\u2019s ability to build sequences around a moveset the audience already knows and loves. The fans are familiar with Taker\u2019s trademark offense, and Angle\u2019s counters create tremendous drama. From a Chokeslam to a Last Ride to a Tombstone, nearly every major maneuver somehow incorporates Angle\u2019s attempts to escape or counter intothe Ankle Lock. These transitions feel meaningful and build toward the finishing sequence.<\/p>\n<p>Speaking of the finish, it\u2019s perfectly executed. The Undertaker locks Angle in Hell\u2019s Gate, and Angle looks as though he\u2019s on the verge of either tapping out or passing out. However, using his technical ability, Angle rolls through into a jackknife pin and catches The Undertaker with a three-count to retain his championship.<\/p>\n<p>It\u2019s a finish that is smart in theory and perfect in execution. It highlights Kurt Angle as a phenomenal wrestler without compromising The Undertaker\u2019s credibility. Angle wins because of his technical ability and awareness, not because he overpowers or outclasses The Undertaker.<\/p>\n<p>The Undertaker\u2019s catalog of great matches is long and diverse, but this one is often forgotten when discussing his greatest performances. It serves as an excellent example of how The Undertaker was not only a fantastic character but also an outstanding in-ring performer.<\/p>\n<p><a href=\"https:\/\/www.youtube.com\/watch?v=t_9c9Px7Eac\">CLICK TO WATCH<\/a><\/p>\n<p><iframe loading=\"lazy\" title=\"FULL MATCH: Kurt Angle vs. Undertaker \u2013 World Heavyweight Title Match: WWE No Way Out 2006\" width=\"500\" height=\"281\" src=\"https:\/\/www.youtube.com\/embed\/t_9c9Px7Eac?feature=oembed\" frameborder=\"0\" allow=\"accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture; web-share\" referrerpolicy=\"strict-origin-when-cross-origin\" allowfullscreen><\/iframe><\/p>\n<div class=\"pwtor-end-article-groups pwtor-entity-placement\" id=\"pwtor-1160256556\"><div id=\"pwtor-398894639\" role=\"region\" aria-label=\"Advertisements\"><div align=\"center\" data-freestar-ad=\"__336x280\" id=\"pwtorchcom_medrec_3\">\r\n  <script data-cfasync=\"false\" type=\"text\/javascript\">\r\n    freestar.config.enabled_slots.push({ placementName: \"pwtorchcom_medrec_3\", slotId: \"pwtorchcom_medrec_3\" });\r\n  <\/script>\r\n<\/div>\r\n\r\nTHANK YOU FOR VISITING<\/div><\/div>","protected":false},"excerpt":{"rendered":"<div class=\"mh-excerpt\"><p>In November 1990, nearly 36 years ago, The Undertaker made his debut at Survivor Series. From his initial introduction, the uniqueness of the character immediately captured attention and created an undeniable mystique. His distinct look, <a class=\"mh-excerpt-more\" href=\"https:\/\/www.pwtorch.com\/site\/2026\/11\/13\/then-now-forever-the-undertaker-edition-the-evolution-of-the-undertaker-which-was-introduced-36-years-ago-this-month-with-a-look-at-key-matches-with-bret-hart-kurt-angle-shane-mcmahon\/\" title=\"THEN, NOW, FOREVER &#8211; THE UNDERTAKER EDITION: The evolution of the Undertaker which was introduced 36 years ago this month with a look at key matches with Bret Hart, Kurt Angle, Shane McMahon\">[&#8230;]<\/a><\/p>\n<\/div>","protected":false},"author":1,"featured_media":225162,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"_jetpack_newsletter_access":"","_jetpack_dont_email_post_to_subs":false,"_jetpack_newsletter_tier_id":0,"_jetpack_memberships_contains_paywalled_content":false,"_jetpack_hide_featured_image":false,"_jetpack_featured_image_duplicate_dismissed":0,"_jetpack_memberships_contains_paid_content":false,"footnotes":""},"categories":[52,27,6992],"tags":[],"class_list":["post-225161","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-opnionandanalysis","category-specialists","category-then-now-forever"],"jetpack_sharing_enabled":true,"jetpack_featured_media_url":"https:\/\/www.pwtorch.com\/site\/wp-content\/uploads\/post\/2026\/11\/Screenshot-2026-11-13-at-12.10.12-PM.png","_links":{"self":[{"href":"https:\/\/www.pwtorch.com\/site\/wp-json\/wp\/v2\/posts\/225161","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.pwtorch.com\/site\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.pwtorch.com\/site\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.pwtorch.com\/site\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/www.pwtorch.com\/site\/wp-json\/wp\/v2\/comments?post=225161"}],"version-history":[{"count":1,"href":"https:\/\/www.pwtorch.com\/site\/wp-json\/wp\/v2\/posts\/225161\/revisions"}],"predecessor-version":[{"id":225163,"href":"https:\/\/www.pwtorch.com\/site\/wp-json\/wp\/v2\/posts\/225161\/revisions\/225163"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/www.pwtorch.com\/site\/wp-json\/wp\/v2\/media\/225162"}],"wp:attachment":[{"href":"https:\/\/www.pwtorch.com\/site\/wp-json\/wp\/v2\/media?parent=225161"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.pwtorch.com\/site\/wp-json\/wp\/v2\/categories?post=225161"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.pwtorch.com\/site\/wp-json\/wp\/v2\/tags?post=225161"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}