Battling a string of nasty habits and behaviors, the Shawn Michaels of the mid-90s was on a one-way roller coaster to self-destruction. His rough style of cartoonish bumps cost him severely, as in early 1998 he landed awkwardly on a casket during a match with The Undertaker at Royal Rumble 1998, and would have to take time off for surgery. The decision was made to drop the title to the man of the hour, Steve Austin, at a coronation ceremony for the new face of the companycomplete with Mike Tyson as a guest starat WrestleMania XIV. Michaels took a break from in-ring action, appearing here and there as the Commissioner to foil (or join in) the plans of the McMahons, but ultimately took a few years away to find himself spiritually and turn his life around. A reformed Christian man, Shawn Michaels burst through the proverbial curtain and into the hearts of many fans when he triumphantly returned to the squared circle to duke it out with long-time friend and D-Generation X stablemate, Triple H at SummerSlam 2002. That feud kicked off a second act in the storied career of perhaps the greatest in-ring performer of all-time, which stood up to the best matches he had in the 90s, long before those bouts with personal demons, his own ego, and injuries came to derail his track to becoming the greatest professional wrestler of all-time. https://www.youtube.com/watch?v=tqMpjFn-M1o All good things must definitively end, however. The phoenix rose from the ashes, burned brighter than ever, and was extinguished at the height of its descent. The toils of physicality in the ring had taken their toll on Shawn, and the phoenix was crashing back down to Earth in a flaming heap of glory. A lengthy feud with The Undertaker at WrestleMania put the writing on the wall for wrestling fans, and when Shawn put his career on the line, we knew we were seeing the ending to one of the sports greatest stories. Shawn went out on his own terms, unlike the next man on our list.
David McCutcheon is an American freelance journalist and writing consultant. Over the course of sixteen years, he has written for the likes of IGN, Future US, GamesRadar, PlayStation Magazine, Shout! Factory, and many others in the fields of video games, movies, and more. He lives in St. Louis, Missouri with his wife. You can find him on Twitter @ZoopSoul.