The Rockers (Shawn Michaels and Marty Jannetty) debuted at a WWF live event on July 7, 1988. The team was a mid-card stalwart of television and pay-per-view shows for the next two years; during this time, Michaels headlined his first pay-per-view for the WWF when The Rockers were involved in the 4-on-4 Survivor Series match main event of the 1989 Survivor Series.
In October 1990, The Rockers were scheduled to win the WWF Tag Team Championship from The Hart Foundation (Bret Hart and Jim Neidhart), as Neidhart, half of the championship team, was in the process of negotiating his release from the company. The match was taped with The Rockers winning the belts, but soon after, Neidhart came to an agreement with management and was rehired. The belts were returned to the Hart Foundation, while the title change was never broadcast or even acknowledged on television. The Rockers continued their partnership, eventually splitting on December 2, 1991 during an incident on Brutus "The Barber" Beefcake's televised Barber Shop talk show promotional segment. Michaels superkicked Jannetty and threw him through a glass window on the set of Beefcake's talk show. Jannetty returned to the WWF the following year and enjoyed moderate success before leaving the company in 1994, while Michaels became a prominent villain of the early to mid-1990s as "The Boy Toy."
At the suggestion of "Mr Perfect" Curt Hennig, Michaels adopted the nickname "The Heartbreak Kid." Along with his new name came a new gimmick as a vain, cocky villain. He was put together with mirror-carrying manager, Sensational Sherri, who, according to the storyline, had become infatuated with him. Sherri even sang the first version of his new theme music, "Sexy Boy."
At WrestleMania VIII, in his first pay-per-view singles match, Michaels defeated El Matador: both men had simultaneously eliminated each other from that year's Royal Rumble. He subsequently became a contender to the promotion's singles championships. Michaels failed to wrest the WWF Championship from champion "Macho Man" Randy Savage, in his first opportunity to compete for that title at British pay-per-view UK Rampage, held on on April 19 at the Sheffield Arena. He failed to win the WWF Intercontinental Championship from Bret Hart in the WWF's first-ever ladder match at a Wrestling Challenge taping on July 21. He, however, won the title from The British Bulldog on the October 27, 1992 episode of Saturday Night's Main Event, which aired on November 14. Shortly thereafter, he faced Hart for the WWF Championship in the main event of the 1992 Survivor Series, but lost the match. Originally the secondary main event, Michaels and Hart became the primary main event after The Ultimate Warrior was unable to compete, and was replaced by Mr. Perfect in the tag team match that involved Randy Savage against the team of Ric Flair and Razor Ramon. During this time, Michaels and Sherri split and he engaged himself in a feud with former tag team partner Marty Jannetty. Michaels lost the Intercontinental Championship to Jannetty on Monday Night Raw on May 17, 1993. He then regained it on June 6 with the help of his debuting "bodyguard" Diesel.
In September 1993, Michaels had quit the company, after it was announced that he had failed to defend his title enough times during a set period. He returned to WWF television in November at the Survivor Series pay-per-view, substituting for Jerry Lawler, who was dealing with legal issues, in a match pitting himself and three of Lawler's "Knights" against the Hart brothers, Bret, Bruce, Keith, and Owen.
He soon entered a staged rivalry with Razor Ramon, who had won the vacated Intercontinental Championship, during Michaels' absence. Since Michaels had never been defeated in the ring for the title, he claimed to be the rightful champion and even carried around his old title belt. This feud culminated in a ladder match between the two at WrestleMania X. Michaels lost the match, which featured both his and Ramon's belts suspended above a ladder in the ring. Over the next few months, Michaels battled various injuries and launched the Heartbreak Hotel television talk show segment, mainly shown on WWF Superstars.
On August 28, 1994, Michaels and Diesel captured the Tag Team Championship from The Headshrinkers (Samu and Fatu). The next day, at SummerSlam, Diesel lost the Intercontinental Championship to Ramon when Michaels accidentally superkicked Diesel. This triggered a split between Michaels and Diesel, a storyline that was drawn out until Survivor Series that November. Michaels went on to win the Royal Rumble in 1995, which set up a championship grudge match at WrestleMania XI against Diesel (who had gone on to win the WWF Championship from Bob Backlund). As part of the storyline, Michaels recruited Sycho Sid as his bodyguard for the build-up, lost the match, and was attacked by Sid the following night. After this, Michaels took time off, because Vince McMahon wanted Michaels to become a fan favorite.
Michaels returned to the ring, as a fan favorite, in May 1995. He went on to defeat Jeff Jarrett in July at the In Your House pay-per-view event, to win his third Intercontinental Championship. This led to a title defense against Razor Ramon at SummerSlam, in a ladder match, which Michaels won. Around this time Michaels became the leader of a backstage group known as The Kliq.
In October 1995, he was legitely attacked by several men outside a bar in Syracuse, New York. Shortly afterwards, at the In Your House: Great White North pay-per-view, Michaels was declared unable to compete by the WWF and forfeited the Intercontinental Championship to Dean Douglas, who in turn Douglas lost the championship to Kliq member Razor Ramon. The next month, during a match with Owen Hart on an episode of Monday Night Raw, Owen performed an enzuigiri that struck the back of Michaels' head. They continued the match, but Michaels collapsed in the ring, supposedly because he had suffered a concussion.
After teasing a retirement, Michaels returned to the WWF at the Royal Rumble match in 1996, which he wound up winning for a second year in a row, to receive a WWF Championship match in the main event at WrestleMania XII. Around this time, Jose Lothario became Michaels' on-screen manager. At WrestleMania XII, Michaels defeated WWF Champion Bret Hart in the overtime of their sixty minute Iron Man match, which had ended in a scoreless tie. On May 19, 1996, Michaels and his fellow Kliq members were involved in the incident known as "Curtain Call". Diesel and Razor Ramon were about to leave WWF. After Michaels won a match against Diesel, Ramon and Hunter Hearst Helmsley came to the ring and joined Michaels and Diesel in a group-hug. As Diesel and Helmsley were seen as villains at the time, in contrast to Michaels and Ramon, this constituted a breach of "kayfabe", as acting out of character, which was rare and controversial at the time. Michaels' championship reign ended at the 1996 Survivor Series event, where he lost to Sycho Sid, his former bodyguard. Michaels recaptured the championship from Sid in January 1997 at the Royal Rumble.
On a special episode of Raw dubbed Thursday Raw Thursday, Michaels vacated the WWF Championship; he explained to fans that he was informed by doctors that he had conjured a knee injury, and that he had to retire. His speech was regarded as controversial, as Michaels was allegedly unwilling to lose to Bret Hart at WrestleMania 13 (since it was noted that he was going to have a rematch with Hart at WrestleMania). Michaels contemplated thoughts of retirement and stated that he "had to find his smile again," which he had "lost" somewhere down the line. After knee surgery by Dr. James Andrews, Michaels returned a few months later, briefly teaming with Stone Cold Steve Austin to win the WWF Tag Team Championship.
Shawn Michaels briefly left the WWF in June 1997 after a real life backstage fight with Bret Hart at a house show, which stemmed from Michaels making an on-air remark alleging that Bret (who was married at the time) was having an affair with then WWF Diva Sunny. Shawn Michaels and Stone Cold Steve Austin were still WWF Tag Team Champions at the time during the ongoing feud with The Hart Foundation and a tournament was made to decide new Tag Champions. Michaels would return later that summer in July. At SummerSlam, Michaels officiated the WWF Championship match between WWF Champion The Undertaker and Bret Hart. The match ended in controversial fashion, with Michaels hitting Undertaker with a chair (unintentionally, as he was aiming for Bret after he spat in his face). Michaels was then forced to award the championship to his nemesis, Bret Hart. The next night on Raw, signs of a heel turn started to show as Michaels told the WWF fans what happened at SummerSlam was an accident and that he would deal with the Undertaker when the time came. At WWF One Night Only, held in Birmingham, England in September, Michaels defeated The British Bulldog to capture the WWF European Championship. The fans at the event were so appalled at the result of the match they booed Michaels out of the building, to the extent that they littered the ring with garbage, cementing his second heel turn. With this win, Michaels became the first Grand Slam Champion. At the October pay-per-view event, In Your House: Badd Blood, Michaels and Undertaker participated in the first Hell in a Cell match. During the match, it saw Michaels fall off the side of the 15-foot (5 m) high structure through a table and saw him as the winner in the match.
In the fall, Michaels joined forces with real-life friend, Hunter Hearst Helmsley (Triple H), Hunter's then-girlfriend, Chyna, and Rick Rude to form the stable, D-Generation X (DX). Moving away from the family-oriented product, this marked the beginning of the WWF Attitude Era. Michaels continued his rivalry with Bret Hart and his reformed Hart Foundation, which was now a pro-Canada stable. Michaels taunted the group and Canada by engaging in acts, such as blowing his nose with and humping the Canadian Flag. Michaels' feud with the Hart Foundation culminated in a championship match at Survivor Series in 1997 against Bret Hart. Michaels came out of this match, dubbed by fans the "Montreal Screwjob", as the WWF Champion. Michaels now held both the WWF and European championship at the same time. Michaels, dropped the European Championship to D-Generation X member, Hunter Hearst Hemsley, during a farcical match.
At the 1998 Royal Rumble, Michaels received a serious back injury in a Casket match against The Undertaker. 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 after losing the WWF Championship to Steve Austin at WrestleMania XIV.
After being gone for 5 months, Shawn Michaels would make a surprise return to the WWF as a guest commentator on the July 13th episode of Raw is War. Michaels would continue to make non-wrestling appearances on WWF programming, and on November 23, 1998, 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 January 4, 1999 on Raw, Michaels re-joined DX as a fan favorite, but disappeared from WWF television for a few months to have back surgery, and by the time he had returned, DX had broken up.
Michaels made occasional appearances as the WWF Commissioner during the spring and summer of 1999, but remained absent from television until May 15, 2000, upon which he returned on Raw to announce himself as the special guest referee for the Iron Man match between The Rock and Triple H at Judgment Day. One month later, Michaels briefly reappeared on Raw to hand over the role of Commissioner to Mick Foley and afterwards did not make any in-ring appearances until mid-2002, appearing only once on WWF television to make a speech at WWF New York during Armageddon 2000. Michaels also had no part at all in the Invasion storyline.
In 2002, Michaels returned to WWE television after 18 months of absence. On the June 3 episode of Raw, he was announced as a new member of the recently-formed New World Order (nWo) stable by Kevin Nash. After the nWo had disbanded, Triple H appeared to make amends with Michaels. This was solidified when Michaels pleaded Triple H to return to Raw. Later on, they came down to the ring sporting their DX music and attire. When the pair was about to perform their trademark "Suck It" taunt, Triple H turned on Michaels by performing a Pedigree on him. Continuing the angle, a week later, Triple H attacked Michaels from behind in a parking lot and put his head through a car window, in storyline. In response, Michaels challenged Triple H to "a fight" (a non-sanctioned match) at SummerSlam, which Triple H accepted, laying the foundation for a rivalry that would last for several years. In his first official wrestling match since WrestleMania XIV, Michaels won at SummerSlam, but was attacked by Triple H with a sledgehammer after the match. At Survivor Series, Michaels won the World Heavyweight Championship from Triple H in the first-ever Elimination Chamber match. Michaels' reign as champion came to an end a month later when he lost the championship to Triple H in a Three Stages of Hell match, a series of three matches in which wrestlers attempt to win the majority of matches, at Armageddon.
Michaels then began a rivalry with Chris Jericho, after Jericho claimed that he was the next Shawn Michaels. On January 13, 2003, after Jericho won a battle royal to select his entry number for the Royal Rumble, choosing number two in order to start the match with Michaels, who had already been named number one. At the Royal Rumble, Jericho, with the help of Christian, eliminated Michaels. Michaels defeated Jericho at WrestleMania XIX. Despite this, Michaels was low-blowed after hugging with Chris Jericho.
As a part of an ongoing feud with Triple H, the two competed alongside Chris Benoit in the main event match at WrestleMania XX for the World Heavyweight Championship. The former DX partners both came up short in the match, however, as Benoit won the championship. At Bad Blood in June, Michaels lost to Triple H in a Hell in a Cell match. Four months later, he lost a World Heavyweight championship match against Triple H, after Edge interfered at Taboo Tuesday, when the fans voted for him ahead of Edge and Chris Benoit to face Triple H one more time. Following this, Michaels was out of action for a few months with a legit torn meniscus.
At the Royal Rumble in 2005, Michaels competed in the Rumble match and eliminated Kurt Angle. In seeking revenge, Angle re-entered the ring and eliminated Michaels, and thus placed him in an ankle lock submission hold, outside of the ring. Michaels issued a challenge to Angle for a match at WrestleMania 21, which Angle accepted when he appeared on Raw to attack Michaels. The following week on Raw, Marty Jannetty and Michaels had a one time reunion as The Rockers and defeated La Résistance (Robért Conway and Sylvain Grenier). Three days later on SmackDown!, Angle defeated Jannetty, after Angle made Jannetty submit to the ankle lock. To send a "message" to Michaels, Angle also humiliated Michaels' former manager, Sensational Sherri, when he applied the ankle lock hold on her. At WrestleMania 21 in April, Angle defeated Michaels by submission, again with an ankle lock. Two months later, at a WrestleMania 21 rematch, Michaels defeated Angle at the Vengeance pay-per-view event.
Following the events of WrestleMania 21, the next night on Raw, Muhammad Hassan and Daivari came out to confront and assault Michaels. On the April 11 episode of Raw, Michaels approached authority figure Eric Bischoff, in which he demanded a handicap match with Hassan and Daivari, a match consisting of one wrestler or team of wrestlers facing off against a team of wrestlers with numerical superiority such as two against one, or three against two. Bischoff refused to schedule the match, but informed Michaels to find a partner and he would grant him the match. Michaels then made a plea for Hulk Hogan to come back and team with him. On the April 18 episode of Raw, Hassan again led an attack on Michaels until Hogan appeared to save Michaels and accept his offer. At Backlash, Hassan and Daivari lost to Hogan and Michaels when Daivari was pinned. On the July 4 episode of Raw, Michaels and Hulk Hogan had a tag team match, which they won. During the post-match pose, Michaels hit Hogan with his superkick, knocking Hogan to the ground and making Michaels a villain for the first time since returning in 2002. The following week on Raw, Michaels appeared on Piper's Pit where he superkicked Roddy Piper and then challenged Hogan to a match at SummerSlam. Hogan defeated Michaels at SummerSlam, and after the match Michaels extended his hand to him, saying "I needed to know, and I found out" and he and Hogan shook hands. Michaels left the ring to allow Hogan to celebrate with the crowd, and Michaels once again became a fan favorite.
On the December 26, 2005 episode of Raw, Vince McMahon lauded Michaels for his part in the "Montreal Screwjob". Michaels said he was only being loyal to his company, he had moved on, and McMahon should move on as well. McMahon then began setting unusual stipulations for Michaels' matches and interfering on behalf of Michaels' opponents. During the Royal Rumble, McMahon made his way to the ring, and as Michaels stared at McMahon, Shane McMahon made a surprising appearance, eliminating Michaels from the match. On the February 13 episode of Raw, McMahon tried unsuccessfully to force Michaels to sign retirement papers. The following week, Michaels won a handicap match against the Spirit Squad (Kenny, Johnny, Mitch, Nicky and Mikey) and after the match, Michaels' former partner, Marty Jannetty, came down to help Michaels from the assault by the Spirit Squad. After the two reunited, McMahon offered Jannetty a contract if he "kissed his backside." The following week, Jannetty refused McMahon's offer and instead took Chris Masters' "Masterlock challenge." Michaels tried to help Jannetty, which ultimately resulted in Shane attacking Michaels and forcing him to kiss his father's backside. At Saturday Night's Main Event, Shane defeated Michaels in a Street Fight, a match without disqualifications and where scoring conditions can occur anywhere, after he applied a sharpshooter on Michaels, which led to McMahon immediately ordering for the bell to be rung, even though Michaels did not submit, which was an allusion to the "Montreal Screwjob". Despite interference from the Spirit Squad and Shane, Michaels defeated McMahon at WrestleMania 22 in a No Holds Barred match, a match where there are no disqualifications. At Backlash, The McMahons (Vince and Shane) defeated Michaels and "God" in a tag team match, with help from the Spirit Squad in a no disqualification match. On the May 22 episode of Raw, the Squad was scripted to injure Michaels' knee. This was angle was written so that Michaels could have surgery on his knee, which had been legitely injured for some time.
In 2006, a series of events took place which suggested a reunion of Michaels and Triple H as DX. They began at WrestleMania 22, where both Michaels and Triple H performed the crotch chop, during their matches. On Raw, the two continued to deliver chops, as Michaels feuded with Vince McMahon and Triple H went for the WWE Championship, repeatedly butting heads with Vince McMahon in the process. On the June 12 episode of Raw, DX officially reunited. During Triple H's gauntlet match, which had him compete against the Spirit Squad. Michaels came in to help Triple H, and the two did the DX "crotch chops." At Vengeance, DX defeated the Spirit Squad in a 5–on–2 handicap match. They also defeated the Spirit Squad at Saturday Night's Main Event in a 5-on-2 elimination match and defeated The McMahons at SummerSlam. At Unforgiven, DX once again defeated the McMahons and ECW World Champion The Big Show in a Hell in a Cell match.
At Cyber Sunday, DX took on Rated-RKO (Edge and Randy Orton). The fan-selected referee Eric Bischoff allowed the illegal use of a steel chair to give Rated-RKO the ill-gotten win and the plaudit of being the first tag team to defeat DX in a tag team match since their reformation in June 2006. At Survivor Series, however, Team DX emerged victorious against Team Rated-RKO in a clean sweep victory. At New Year's Revolution, Triple H suffered a legit torn right quadriceps during their match with Rated-RKO. Rated-RKO claimed victory over DX, citing Triple H's injury, as the "end" of DX. On January 15, Michaels lived up to his word of "dealing" with Rated-RKO, from his comments the previous week before, when he took out Randy Orton with a con-chair-to after a handicap match against Edge and Orton.
On the January 29 episode of Raw, Michaels captured the World Tag Team Championship with WWE Champion John Cena after defeating Rated-RKO. He then defeated both Edge and Orton in a Triple Threat number one contender's match on another episode of Raw to earn a shot at the WWE Championship. At WrestleMania 23, Cena retained the championship, after he made Michaels submit to the STFU. The next night on Raw, Michaels and Cena competed in two back-to-back ten team battle royals, winning the first and losing the titles in the second to The Hardys (Matt and Jeff) when Michaels threw Cena over the top rope. Michaels' feud with Cena continued and he faced off with Cena, Edge and Randy Orton in a Fatal Four-Way Match at Backlash for the WWE Championship. Cena retained the championship when Michaels performed Sweet Chin Music on Cena causing him to fall on Orton, which gained Cena the pinfall.
Michaels then entered a feud with Randy Orton when Orton claimed that he could beat Michaels. The week before their scheduled match at Judgment Day, after Michaels won a match against Edge, Orton interfered, punting Michaels in the head. Orton assaulted Michaels again, just prior to their match at Judgment Day, interrupting Michaels' interview segment. Michaels collapsed during the course of their match, causing Orton to win by referee stoppage. Afterwards, Orton continued the beating, when he performed an RKO to a fallen Michaels. Michaels was then removed out of the ring in a stretcher. During the feud, Michaels conjured a storyline concussion. This injury was used to keep Michaels out of action, as he required surgery for his knee. Michaels made his return on the October 8 episode of Raw, performing a superkick to newly-crowned WWE Champion, Randy Orton, during his title ceremony at the end of the show and then celebrating over the knocked-out champion as Vince McMahon watched. At Cyber Sunday, Michaels was voted by the fans to face Orton for the WWE Championship; though he won via disqualification when Orton hit Michaels with a low blow, which resulted in Orton retaining the championship. Michaels got another opportunity at the WWE Championship, when he was granted his rematch against Orton at Survivor Series. In their match, Michaels was banned from using Sweet Chin Music upon request by Orton, referring to as Michaels superkicking Orton week after week. Michaels lost the match, when Orton performed an RKO for the win.
As part of the storyline involving Ric Flair, Michaels faced Flair in a Career Threatening match at WrestleMania XXIV, in which he won by performing Sweet Chin Music and thus ending Flair's career. Afterwards, Batista confronted Michaels about his actions at WrestleMania, calling him selfish and egotistical. The two faced off at Backlash with Chris Jericho as the guest referee. Michaels won after faking a knee injury and performing Sweet Chin Music. Jericho then confronted Michaels on this matter, in which Michaels admitted to faking the injury in order to defeat Batista. Michaels then defeated Jericho at Judgment Day. At One Night Stand, Michaels lost to Batista in a stretcher match, thus ending their feud. On the June 9 episode of Raw, Michaels was attacked by Chris Jericho during his talk show segment, The Highlight Reel, being thrown directly through a television screen. The following week, it was revealed that, within the context of the storyline, Michaels had suffered a detached retina. At The Great American Bash, a match between Michaels and Jericho was scheduled, in which Jericho assaulted Michaels' eye, which caused Jericho to win by referee stoppage.
A month later at SummerSlam, Michaels was scripted to announce his retirement from professional wrestling, though the staged rivalry between Jericho and himself continued after Jericho punched Michaels' wife in the face. On the August 25 episode of Raw, Michaels denounced his decision to retire and challenged Jericho to an unsanctioned match at Unforgiven, which Jericho accepted. The following week, Michaels and Jericho held a scripted official contract signing for the unsanctioned match. During the contract signing, a confrontation with Jericho occurred. A predicament ensued when Michaels suffered a small tear on his left triceps, though Michaels was medically cleared to compete in the match. At Unforgiven, Michaels defeated Jericho, after the referee stopped the match, due to the severity of the beating Michaels was giving Jericho. It was at the same September event that Jericho replaced CM Punk in the World Heavyweight Championship scramble match, which saw him win the match and become World Heavyweight Champion. The following month at No Mercy, Michaels met Jericho in a ladder match in which Jericho defended the championship against Michaels. At the event, Jericho defeated Michaels to retain the title.
In December 2008, Michaels accepted an offer to become an employee of John "Bradshaw" Layfield (JBL). The storyline was that Michaels had lost his family's personal savings due to the global recession, forcing him to accept JBL's offer of employment. After failing to secure JBL the World Heavyweight Championship against John Cena at the Royal Rumble, Michaels agreed to take part in an "All or Nothing" match at No Way Out in February. Michaels won the match, letting Michaels out of his one-year contract with JBL immediately while still receiving full payment. Michaels became the first person to defeat Vladimir Kozlov on the March 2 episode of Raw, and as a result earned the right to face The Undertaker at WrestleMania XXV in April. At the event, The Undertaker defeated Michaels to extend his WrestleMania winning streak to 17–0. After WrestleMania, Michaels took a hiatus from WWE.
Michaels returned to WWE programming in a series of segments that aired on the August 10, 2009 episode of Raw, where he had scripted left the WWE. Triple H met with Michaels at an office cafeteria in Texas where he was working as a chef; throughout the segments, Triple H would try to convince Michaels to return to WWE and reform DX. After several incidents during the segments, Michaels agreed to team with Triple H to face The Legacy (Cody Rhodes and Ted DiBiase) at SummerSlam. At the pay-per-view event, DX defeated Legacy. The two teams would exchange victories, with their feud concluding in October. Two months later, at TLC: Tables, Ladders & Chairs, DX defeated Chris Jericho and The Big Show to win the Unified WWE Tag Team Championship in a Tables, Ladders, and Chairs match (TLC). On the January 4, 2010 episode of Raw, Michaels buried the hatchet with long-time rival Bret Hart, as they shook hands and hugged in the ring. In contrast to the storylines featured on the show, this was in fact a real-life reconciliation which laid to rest animosities surrounding the Montreal Screwjob. While some cast doubts on its sincerity, both men have confirmed that it was indeed genuine. DX lost the Unified Tag Team Championship in a Triple Threat match to the team of The Miz and Big Show on the February 8 episode of Raw, the match also included The Straight Edge Society (CM Punk and Luke Gallows). At the Elimination Chamber pay-per-view, Michaels cost The Undertaker the World Heavyweight Championship in the main event. At WrestleMania XXVI, Michaels lost to The Undertaker and, as a result, he was forced to retire due to the match stipulation, the same way HBK ended Ric Flair's career. The following night, on the March 29 episode of Raw, Michaels gave an emotional farewell speech, departing with the familiar sentence, "Shawn Michaels has left the building."
On the December 14 episode of Raw, Michaels won the Slammy award for Moment of the Year for his match against The Undertaker at WrestleMania XXVI. Michaels made an appearance via satellite to accept the award. Three days later, he announced a long-term deal with WWE, where he will serve in an ambassadorial role. Michaels made his first live appearance at a WWE show since the night after WrestleMania at the December 11 Tribute to the Troops taping, where he and Triple H made a special appearance for a one-night only DX reunion. Michaels appeared on the January 10, 2011, episode of Raw, where it was announced he was to be inducted into the WWE Hall of Fame class of 2011. After being ridiculed by Alberto Del Rio, Michaels hit Del Rio with Sweet Chin Music. On the March 28 episode of Raw, Michaels addressed Triple H and The Undertaker about their match at WrestleMania XXVII. Michaels was inducted into the WWE Hall of Fame on April 2 by Triple H. The two were also joined by Kevin Nash (who had returned to WWE previously to participate in the recent Royal Rumble) and Sean Waltman, reuniting the majority of The Kliq. He further made an appearance on the June 27 episode of Raw where he was confronted by CM Punk, and superkicked David Otunga and Michael McGillicutty. Later that night when Diamond Dallas Page made a special appearance and was interrupted and threatened by Drew McIntyre, Michaels superkicked McIntyre. He made another appearance on February 13, 2012 to confront his friend Triple H about not accepting The Undertaker's challenge. He also declared the fact that he was the special guest referee for the match between The Undertaker and Triple H inside Hell in a Cell at Wrestlemania XXVIII. On August 6, the live audience experienced "Shawn Michaels Appreciation Night" at a Raw taping. Shawn made an appearance on TV where he was confronted by Brock Lesnar. Shawn also appeared after the show as part of the Appreciation Night ceremonies. On the January 24 edition of WWE NXT, Michaels appeared to announce a tournament to crown the inaugural NXT Tag Team Champions. Afterwards, he had an off-screen DX reunion with Kevin Nash as well.
On April 1, 2013 episode of Raw Michaels returned to offer his moral support for Triple H against Lesnar at WrestleMania by being Triple H's manager. As a result at WrestleMana 29 Triple H defeated Brock Lesnar to keep his career on the line and Michaels would launch a super kick to Paul Heyman. Michaels returned on the May 27 episode of Raw in a backstage segment with John Cena, while also appearing on the Summerslam 2013 Kickoff.
On the 7 October episode of Raw, Michaels returned and, after a poll on the WWE App, became the special guest referee for the Hell in a Cell match between Daniel Bryan and Randy Orton over the vacant WWE Championship. At Hell in a Cell, Michaels delivered Sweet Chin Music to Bryan and allowed Orton to win the match and become the new WWE Champion, possibly turning heel for the first time since 2005. The next night on Raw, Michaels told Bryan that Triple H was his best friend and always will be, and was upset at how Bryan attacked Triple H during the Hell in a Cell match the previous night. Michaels would then degrade Bryan for not showing him the respect he deserves. Bryan would put Michaels in the Yes Lock to end the segment. On December 9, he presented Bryan with the award for Superstar of the Year. Later that night, Bryan hit Michaels with a running knee after Michaels had super-kicked CM Punk.
On the August 25, 2014 episode of Raw, Michaels returned along with fellow legends Hulk Hogan and Ric Flair in a legends panel segment, where he predicted Bray Wyatt to win the rumble. All three legends then became involved in an altercation with Big Show. Michaels would appear at WrestleMania 31, interfering as a member of DX in the Sting vs. Triple H match, delivering Sweet Chin Music to Sting. At a WWE tour in Australia Michaels was confronted by Bo Dallas and was called a has-been and got a Sweet Chin Music for his troubles turning face again in the process. Michaels appeared on the October 19, 2015 episode of Raw, confronting Seth Rollins who was cutting a promo on relieving Kane of his duties as Director of Operations.
At WrestleMania 32, Michaels made an appearance during the event in his in-ring attire, confronting The League of Nations alongside Mick Foley and Stone Cold Steve Austin where Michaels delivered Sweet Chin Music to Alberto Del Rio and King Barrett before celebrating with Foley, Austin and The New Day.