Shawn was born on July 22, 1965 in Chandler, Arizona, the last of four children - Randy, Scott and Shari. 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. He knew he wanted to become a professional wrestler at the age of twelve. Shawn was already an athlete; his career began at the age of six when he started playing football. He was a stand-out Linebacker at Randolph High School and eventually became Captain of the football team. After graduating, Shawn attended Southwest Texas State University in San Marcos, Texas, but soon realized that college life was not for him. Then he began pursuing the career of a professional wrestler.

He was then trained by Mexican professional wrestler Jose Lothario. Lothario suggested that Shawn go by the ring name Shawn Michaels. After his training with Lothario, before joining WWE, Shawn Michaels began his wrestling career with Mid-South Wrestling and American Wrestling Association (AWA). There, Shawn partnered up with Marty Jannetty to form The Midnight Rockers and won the AWA World Tag Team Championship on two separate occasions. After signing with WWF, Shawn abandoned the tag team division to work in singles matches and received a new gimmick as "The Heartbreak Kid." He was alleged to be the leader of a backstage group known as The Clique, which was known for breaking character during the Madison Square Garden "Curtain Call" incident in 1996. The following year, Shawn joined forces with Hunter Hearst Helmsley and Chyna to form D-Generation X (DX). This stable was known for pushing the envelope. That same year, Shawn took part in one of the most controversial matches in wrestling history dubbed as the "Montreal Screwjob." After a crippling back injury forced him to retire following his WWF Championship loss at WrestleMania XIV, Shawn opened a wrestling academy, in which he trained upcoming wrestlers. He made his in-ring return at SummerSlam in 2002. In 2006, Shawn and Triple Hbriefly reformed DX.

Overall, Shawn is a four-time world champion: a three-time WWE Champion, and a one-time World Heavyweight Champion. He was also the winner of the 1995 and 1996 Royal Rumbles and was the first Grand Slam Champion.