Although born in Phoenix, Michaels grew up in San Antonio, Texas. Trained by Jose Lothario, he debuted in 1985 in Texas. He made his national debut in 1986 in the now defunct American Wrestling Association teaming with Marty Jannetty forming a team called the Midnight Rockers.
In 1988, Michaels and Jannetty joined the World Wrestling Federation (now the WWE), still as a team but called simply "The Rockers." Michaels and Jannetty split in late 1991, with Shawn going on to wrestle solo, winning the WWF Intercontinental Title belt in 1992.
In November 1997 Michaels beat Bret Hart in a very controversial match in Montreal. Hart, who then held the WWF title, had reportedly been assured that he would win the match. However, WWF owner Vince McMahon, concerned that Hart was leaving the WWF and taking the belt with him, arranged for the bell to be rung too soon, giving Michaels the match and the title. Several years later, Michaels admitted he knew about McMahon's plan beforehand.
In 1998 a back injury forced Michaels into retirement after losing the WWF World Heavyweight Title to Stone Cold Steve Austin. Michaels would return on occasion to the WWF, but not as a wrestler.
In 2002, Michaels came out of retirement to wrestle a match against his real-life best friend, Triple H. Michaels' return was successful, and he has remained active as a part-time wrestler ever since.