Hickenbottom was born on July 22, 1965 in Chandler, Arizona. The last of four children - Randy, Scott, and Shari are his older siblings - he was raised in a military family and spent a brief part of his early years in Reading, Berkshire, England, but grew up in San Antonio, Texas. As a child, Hickenbottom disliked the name Michael, so his family and friends just called him Shawn. Ever since, he has been referred to as Shawn.

At the 1998 Royal Rumble, Michaels received a serious back injury in a casket match against The Undertaker. Michaels would still go on to win the match and successfully retain his WWF World Heavyweight Championship. Michaels took a back body drop to the outside of the ring and hit his lower back on the casket, causing him to herniate two discs and crush one completely. This rendered Michaels unable to compete in the main event of the following month's No Way Out of Texas: In Your House as advertised, and forced him into retirement a night after losing the WWF World Heavyweight Championship to Stone Cold Steve Austin at WrestleMania XIV as special guest enforcer Mike Tyson turned on DX and Michaels which allowed Austin to gain the victory.  After being away for nearly four months, Michaels would make a surprise return to the WWF as a guest commentator on the July 13 episode of Raw Is War. Michaels would continue to make non-wrestling appearances on WWF programming and on November 23 he replaced Sgt. Slaughter as the WWF Commissioner, a portrayed match maker and rules enforcer, eventually joining Vince McMahon's group of wrestlers called The Corporation as a villain. Throughout late 1998 and early 1999, Michaels made regular television appearances on Raw, in which he scheduled matches, throwing around his authority, and sometimes even deciding the outcome of matches. On the January 4, 1999 episode of Raw Is War, Michaels re-joined DX as a fan favorite, but disappeared from WWF television for a few weeks to have back surgery and by the time he returned DX was on the way of dissolving within the next couple of months.  Michaels made occasional appearances as the WWF Commissioner during the spring and summer of 1999, but remained absent from television after August until May 15, 2000, when he returned on Raw Is War to declare himself the special guest referee for The Rock and Triple H's Iron Man match at Judgment Day. One month later, Michaels briefly reappeared on Raw Is War to hand over the role of Commissioner to Mick Foley and after another appearance in October he did not make any in-ring appearances until mid-2002, although he appeared briefly on television to make a speech at WWF New York during Armageddon in December 2000. Michaels also had no part at all in the Invasion storyline.

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