He entered World Wrestling Entertainment at the end of 1988 as a member of The Rockers tag team with Marty Jannetty. The duo was one of the top teams for the next three years. It was when the team broke up in 1992, however, that Michaels began to grab major attention. Long-time fans remember the infamous Barber Shop appearance, in which Michaels superkicked Jannetty through a plate-glass window on the set of Brutus Beefcake's interview segment. From there, the sky was the limit for the future "Heartbreak Kid."
Within nine months, he had captured the Intercontinental Championship, his first singles title. It was a title he would win on two more occasions. His Ladder Match with Razor Ramon for the IC title at WrestleMania X was one of the greatest bouts of all time. It was the first Ladder Match ever featured on pay-per-view, and helped set the stage for the daredevil style common today.
By 1995, he had elevated himself to main-event status. WWE had long been known as the big man's domain, but Michaels shattered that stereotype. From 1995 to 1996, he won back-to-back Royal Rumbles, becoming one of only three men ever to do so. He also challenged for the WWE Championship at consecutive WrestleManias. It was in 1996, at WrestleMania X11, that Michaels cemented his place in history, emerging from a grueling one-hour Iron Man match against Bret "Hit Man" Hart with the title.
The Heartbreak Kid was one of the most popular champions ever. He would hold the coveted title on three occasions between 1996 and 1998, usually defending it against men far larger than himself. Between the ropes, he exhibited an ability rarely witnessed by fans. Equally capable of taking it to the mat, going aerial, or brawling with the best of them, Michaels was a veritable wrestling chameleon. If anyone doubted whether grappling was an art form, they would be quickly convinced after seeing Shawn compete.
In 2002, HBK shocked the world by making a comeback, jumping right back into the thick of things with then-World Champion Triple H. Michaels competed in a grueling classic with Triple H at SummerSlam '02, and then took the title from him at Survivor Series. Even though he only held it a month, it was clear the comeback was for real. Since then, Michaels has tangled with Ric Flair and Randy Orton, further adding to the laundry list of incredible matches that comprise his career.