Shawn Michaels, considered one of the best wrestlers of all time, wrestled for the World Wrestling Federation/Entertainment from 1988 until his first retirement, due to a serious back injury, in 1998. He did, however, appear without wrestling in several roles from 1998 to 2000, while he made his return to the ring in 2002, until his definitive retirement in 2010. He fought in the main event of the main pay-per-view events from 1989 to 2010 and, in particular, five times in that of the federation's main event, WrestleMania.

He is a four-time world champion, having won the WWF Championship three times and the World Heavyweight Championship once; he then won the royal rumble match twice in a row (1995 edition and 1996 edition) and was the first to complete the Grand Slam Championship. He also won Pro Wrestling Illustrated magazine's Match of the Year award a record eleven times.

He began his career in Mid-South Wrestling, a territory of the National Wrestling Alliance and the American Wrestling Association; in the latter promotion, he formed a tag team with Marty Jannetty known as The Midnight Rockers and the two won the AWA World Tag Team Championship twice. The two then signed with the WWF in 1987, while still under contract with the AWA, where they returned briefly, later signing exclusively with the WWF. After the Rockers disbanded in late 1991, Michaels began working as a singles wrestler under The Heartbreak Kid gimmick, first as a heel and then as a face. He wielded considerable influence over booking decisions as part of a dressing room faction known informally as The Kliq.

In 1997, he formed D-Generation X with Triple H, Chyna and Rick Rude and that same year he took part in one of the most controversial matches in wrestling history, known as the Montreal Screwjob. After suffering a serious back injury at the 1998 Royal Rumble, which forced him to retire after losing the WWF Championship at WrestleMania XIV, he opened a wrestling school, The Shawn Michaels Wrestling Academy, while making his return to the ring in 2002 , at SummerSlam. Michaels and Triple H briefly reformed D-X in 2006, but, following an injury to Triple H, he returned to singles. In 2009, the duo reunited once again to win the Unified WWE Tag Team Championship.

Michaels finally retired in 2010, at WrestleMania XXVI, after losing to The Undertaker in a match where he put his career on the line. In December 2010, he signed a long-term contract with WWE, which consisted of a series of non-ring role appearances. In 2011, he was inducted into the WWE Hall of Fame; the federation described him thus: "Ask every superstar on the WWE roster who is the most gifted athlete of all time and almost everyone will give the same answer: Shawn Michaels."