The Heartbreak Kid: Becoming Shawn Michaels

We are in our fifth year of Peacock’s “Becoming” documentary series, which means our annual Peacock-exclusive WWE documentary is here. Sorry, international viewers, you’ll have to sail the seas for this one. You’ll have to sail the seas for all of them except this one now as they were removed from Peacock with the great purge of everything but old SmackDowns. The good news is that I have reviews of all of them except for “Wooooooo! Becoming Ric Flair.” Last year was WrestleMania IX: Becoming a Spectacle and before that, we had American Nightmare: Becoming Cody Rhodes and Bray Wyatt: Becoming Immortal.

September 30, 2025. Shawn Michaels, Senior VP – Talent Development is slamming Dum-Dums from his bowl and preparing for a NXT taping. Paul “Triple H” Levesque, WWE Chief Content Officer tells us that so many people say their biggest influence is Shawn Michaels. We take a look back at highlights of Shawn’s career as some of the talking heads we’ll see throughout this documentary hit some buzz lines.

July 8, 2025, WWE Performance Center. Matt Bloom tells us about what the Performance Center does while HHH tells us the idea was to train people better and entice talent from other sports. We see Shawn Michaels walk up as Malissa Lappas, Senior Manager – Talent Development Operations tells us that she didn’t even let him in on his first day because she didn’t know who the man in the cutout shorts and flip-flops was. HHH says that Shawn can understand the recruits on every level. Johnny Russo, NXT Vice President / Lead Writer notes how Shawn can connect from an in-ring standpoint but also talks to the newbies on a human level. Joe Hendry, NXT Superstar tells us that Shawn has time for everyone and it’s hard to remember sometimes because he’s the greatest of all-time.

May 6, 1978. Shawn Michaels watches Southwest Championship Wrestling and is captivated immediately. He plays football and baseball but can only remember wanting to be a professional wrestler or a stuntman. We see footage of a young Shawn on Mid-South Wrestling against Buddy Landel. Terry Taylor, NXT Coach says you never saw the inexperience on Shawn and that he always looked like he had been doing it for years. He’s paired with Marty Jannetty in the AWA, saying you go with the opportunities you’re given and they clicked immediately. They have their WWF TV debut. Bret Hart, WWE Hall of Famer was excited because it was a new fresh team for the Hart Foundation. Bruce Prichard, WWE Executive Director calls the Rockers the answer for the youth segment of the audience. Undertaker, WWE Hall of Famer calls them the white meat babyface tag team and Peter Rosenberg, WWE Analyst calls them two hungry hardworking guys trying to get a win. It’s a shame they couldn’t get Marty for this, but God knows what Marty would say at any given time.

Ric Flair, WWE Hall of Famer recalls working with Shawn and how great he was even then as a Rocker in a singles match. Bret knew Shawn had his eyes on a singles career. Shawn: “I don’t know that anybody gets into this line of work wanting to be a tag team.” Prichard walks us through the Barber Shop segment, Rosenberg calling it the greatest tag team breakup of all-time. Shawn tells us that the biggest shock value you could have at the time was that and it thrust him into the spotlight as he wanted.

July 15, 2025. We’re at a NXT writer’s meeting. Andrea Concepcion, NXT Writer/Producer grew up a huge wrestling fan and Shawn introducing himself on her first day was wild. Vic Joseph, NXT Commentator tells Shawn that he typically has to go to the talent to find out their stories and Shawn things the wrestlers should come to him to explain their characters. We flash back to January 11, 1992 and Shawn and Bret hanging out backstage. Roddy Piper told Shawn to never stop being who he is, so he worked who through he was through promos and the words “The Heartbreak Kid” came out of his mouth, taking on a life of its own.

Bret knew Shawn was a great performer and didn’t need anyone’s advice to become a star. Kevin Nash, WWE Hall of Famer, calls the Kentucky Waterfall Mullet was one of the greatest mullets of all-time and somehow Shawn pulled it off. Jimmy Hart, WWE Hall of Famer talks about writing “Sexy Boy” and we get footage of Shawn and Jimmy performing it which is amazing. It has 24 million hits to this day on Spotify. Shawn went out trying to prove himself every night and the company picked up on it as he had his first Intercontinental Title run.

Nash comes in as Diesel, Shawn’s bodyguard, and they were inseparable for years after. The two of them travelled together with Razor Ramon, the Kid and finally Triple H. Behind the scenes they became known as The Kliq. In archival footage, Scott Hall, WWE Hall of Famer: “As long as we scored a goal, I don’t care who gets the praise, I just want that ring. That’s what the Kliq was about.” Michaels says they were a band of brothers that helped each other but probably fed each other’s demons. Bruce tells us that they lived a rock and roll life but every man in the Kliq would steal the show every time in the ring. “If you’re with us, you better get your work right,” says Hall. Nash says there’s no difference between Michaels and Jordan.

WrestleMania XI, Michaels faces Diesel and Bruce says that’s when Vince saw that there was a face side to Shawn. We see Shawn dancing with kids and fans, and this sweeps us right to the Mania Iron Man match with Bret. Bruce says the company was looking for Shawn to be the face of the company and everything was riding on him.

July 30, 2025. Shawn does a promo taping in a blazer and shorts. This flashes us back to March 1, 1996 and Shawn doing a promo in San Antonio about his WrestleMania dream. Shawn enters the arena on the zipline (“WHAT A RIDE!”). Bret tells us that Shawn was in incredible condition and Shawn was the greatest athlete he ever saw in the ring. Shawn wins in overtime and becomes WWF Champion for the first time, the boyhood dream coming true. Shawn couldn’t enjoy it because they couldn’t get the belt on and it didn’t go exactly how he wanted. “It wasn’t a good attitude to have. I was a Gloomy Gus.” Taker tells us about the responsibilities that come with being the champion. “I felt a lot of pressure, and I didn’t handle it well,” Present-Day Shawn tells us as we see Shawn ranting to the camera during a photo shoot.

WCW creates Nitro and Hall and Nash leave, Hall telling us he felt he was hitting the ceiling in WWF. Nash says Shawn was upset because his two best friends and opponents left. Shawn says he was already in a place that wasn’t mentally stable, so it really got him. Bret talks about ratings dropping when Shawn won the title. Shawn got resentful and angry.

August 4, 2025. Shawn knows there are a lot of things in this job that are mentally tough to deal with and he doesn’t see weakness in it. Ethan Page, NXT Superstar tells us that the person he respects the most is the one that relates to him the most, believes in him the most. Shawn tells Bloom that Page reminds him of him so much. Je’Von Evans, NXT Superstar knows he can call Shawn and Shawn will always listen. “I will always be an outlet if it’s something that they need because I care.”

January 27, 1997. Shawn cuts a promo about how sometimes he has a bad attitude. HHH: “I can see him falling apart, he’s collapsing under the pressure.” Taker says Shawn became abrasive and demeaned people. “On a personal level, I wouldn’t have pissed on Shawn Michaels if he was on fire.” Bret: “He was an asshole, a first rate asshole. He said stuff to you, he disrespected you.” Bret knows Shawn’s drug problems were becoming big as Shawn tells us it was blow and weed mostly and the Elvis-life lifestyle sounded cool but there was a time he didn’t care about living past 35. “There’s very realistic functioning drug addicts and that’s exactly what that was. I was never not well on TV, I was not well afterwards.” HHH says Shawn’s moment of existence was his twenty minutes in the ring and then the second he was done, he was loading up. “I knew the stuff I was doing was wrong, but I didn’t care.” He tore his ACL which was a year out at the time. Shawn gives up his belt and loses his smile.

December 17, 2024. NXT in Lowell, MA, the same place Shawn lost his smile. Ethan does a segment that is almost a replica of the smile-losing segment before turning on Je’Von. Ethan was set to do a bit where he trapped Je’Von’s head in a chair and stomped it but was scared of actually hurting Je’Von. We see Shawn go through it with them and telling them to put the chair on HIS head and tells Ethan to stomp as hard as he can. Shawn says he’d never ask anyone to do something he wouldn’t do and he does it. “Wherever you want to go boss man, I’m going to go with you,” says Ethan with huge respect afterwards.

May 5, 1997. Shawn appears on Raw after getting a brace to cover the ACL injury a bit. Business was bad, the nWo was raging and WWF needed something. Shawn became controversial by design and poked the bear every chance he could because he thought it would help. D-Generation X was born as an idea of where the business needed to go according to Shawn. Taker thinks it was fun and cool. HHH says they were trying to be dicks and make the other one laugh. Bret: “Can’t say I liked it.” Here we go. Bret thinks Shawn crossed a line nobody should have crossed as it could have wrecked his marriage. We go to Survivor Series 1997, a show you probably haven’t heard about. We discuss the screw job, another rarely discussed thing in wrestling history, and Bret remembers hearing Vince yell at the time keeper. HHH calls it “high level espionage” and Bret thinks Shawn deserved a bad Academy Award for pretending he didn’t know what was going on. We head to the casket match at the Rumble with Taker and Shawn catching the edge of the casket with his back. “Apparently I had burst the disc and that alters everything in my career from that point on.” Shawn knew he would never wrestle again after WrestleMania, so he really goes off the rails – way too many prescription pills and being able to stay sober for two hours of TV and that’s it – on the road to Mania.

Shawn: “It should have killed me. The reality is it didn’t and a lot of that is Hunter taking care of me and watching after me.” He looks back on it and knows he was a tough son of a gun but his life and career were over.

August 22, 2025. Shawn greets Ilja Dragunov, WWE Superstar at the Performance Center. They discuss Ilja’s rehab and we watch Ilja do some work to come back.

January 12, 1999. Shawn is wheeled into fusion surgery. I wonder if any of the medical center staff thought they’d be in a documentary in 2026 when they were being filmed. Shawn does some segments for a local news station, starting out with segments at high school football games and thought maybe it would be a good living. The love and passion wasn’t there like it was for wrestling and the spiral continued. “I never had anything I could grasp as big as the wrestling business.” We flash to Nitro and Nitro Girl Whisper, Shawn seeing her on TV and falling in love with the most beautiful woman he had ever seen. They meet in January and get married in March. She could recognize that he had problems and eight weeks later she finds out she is pregnant. Now she’s locked in with a man who is on stuff all the time and with a kid. “I was real life in love and enamored with being a dad and I really wanted to be good for all of them because I was filled with love and joy. The only thing that wasn’t wonderful in the picture was YOU.” His kid would say daddy was tired and that was the dam that broke for Shawn.

Shawn finds Jesus. Terry Taylor remembers having a parallel journey and both discovering Jesus at the same time. HHH: “I don’t know anybody that died ODing on religion. If that works for him, good for him. If he’s off drugs, I don’t care how he did it.” Shawn tells us he was saved and felt like HE could walk on water. HHH remembers having conversations and Shawn saying he wanted his son to see him do it and he only trusts one person to consider it. We go to SummerSlam and the match with Shawn, calling it in the ring and HHH realizing quickly that Shawn hasn’t missed a step. They really start going. Taker: “He didn’t miss a beat, it was magic.” HHH felt like he was trying to catch up with Shawn even after Shawn being out for such a period of time. Shawn felt the chills and knew that getting the confidence back was all he needed.

Taker tells us that Shawn didn’t take anything for granted the second time around. Hendry tells us how good it felt to see Shawn win the World Title again and when wrestling is done right, nothing is better, and Shawn’s matches achieved that. Bruce calls it a chance for Shawn to right his wrongs. Shawn: “I was willing to give it my all but at least still have time at home. I wanted to be a part of their lives.” His wife and children watch him wrestle WrestleMania against John Cena.

August 26, 2025. Cheyenne Hickenbottom, Shawn’s Daughter tells us about growing up with her dad being Shawn Michaels. “He was just my dad.” He just wants to put on a good show and go home to his kids. HHH gets Cheyenne a job with the hair and makeup department and she’s worked there ever since. Cameron Hickenbottom, Shawn’s Son surprises Shawn at the PC. He’s joined the WWE creative department and helps frame photos of Shawn. Shawn knows they get held to a different standard and he couldn’t be more proud of both of them. Man, I kind of love seeing Dad Shawn.

September 3, 2025. Shawn is in his home gym stretching. The older he gets, the more he needs the mobility and shows us the watch he got for himself and for Ric Flair for…

March 30, 2008. Shawn retires Flair, at least in WWE land. Flair tells us Shawn told him to let him lead and he did. Shawn loves to talk about that match and how much it reminds him how much he loves the business. He got to do his version of “Naitching” which is “spending a lot of money on stuff you don’t need.” We see him giving Ric the watch and then moved on to have the opportunity with Taker at WrestleMania 25. Taker’s friendship with Shawn had grown so much after his return. “Opposite in every way and that’s freakin’ awesome,” quips Shawn. Taker knew they were going out to steal the show and they did. Ethan calls it one of the greatest matches of all-time, Taker says it is the best match he’s ever been in and it took the least amount of effort. Shawn felt like it was the first time he’d be okay with it being his last match.

They do it again a year later, this time Shawn’s retirement match (ignoring the Saudi match that we are all okay with pretending didn’t exist). Shawn calls the match going out on his own terms, art echoing life. We see backstage footage of Cheyenne bawling and giving Taker the evil eye which is adorable.

March 29, 2010. Shawn thanks the crowd. Taker knows Shawn was fulfilled and at peace. Shawn leaves the arena with his kids. Shawn wasn’t involved with the business at all as we see a clip of his hunting show. He would see Hunter once in a blue moon when he’d do guest appearances and HHH’s in-ring career would wind down a bit too, HHH moving into the creation of NXT. HHH with that last grasp of hair is always weird. He brought Shawn to the PC a few times and could see the spark in Shawn. They went on family vacations to theme parks and Shawn would go to “work.” They rented a house and by the time vacation was over, Shawn and family made the decision to pack up and move to Florida. Bloom knew that Shawn would jump all-in. HHH knew he didn’t have a new coach; he had Shawn Michaels. Drew McIntyre, WWE Superstar tells us he’d drive ten hours to work with Shawn. Taker: “Who else would you want teaching the next generations of sports entertainers?”

Bloom laughs at HBK wanting his own class. Shawn tells the students to listen to the crowd and not the action. They go back and watch the matches with the lights off and their eyes closed, just listening, and then catching on as they understand what he’s talking about. Shawn Spears, NXT Coach/Superstar remembers working with Eric Young and Shawn helping them find their way to a match finish. In fifteen seconds, Shawn thought of something they took weeks to figure out. Shawn told HHH he didn’t want the responsibility of the job, but he knew Shawn would come back for more. Hunter talks about how much fun he was having with NXT before Shawn, but having his best friend really made it. Shawn remembers it feeling like being in the car talking about wrestling with his best friend again. Bloom is always amazed listening to Shawn and Hunter talk. Hunter knew if he had to move up the line, Shawn could handle it and then it happened.

August 19, 2021. WWE tryouts in Vegas. HHH gets sick on the tour and thinks he has the flu, then gets the call telling him to pack a bag and have his wife drive him to Yale because he’s in heart failure. Shawn calls it a blur. Shawn steps in for HHH. The responsibility was something he didn’t want but he would never say no for Hunter who made sacrifices for him at times when it was tough to do. “I felt like maybe I could pay him back for what he had done so selflessly.” Shawn tells the NXT crew they made him fall back in love with it all.

Shawn says every week of TV is a struggle, but he just does his job and does it well. “I’m not sick of it yet, so until somebody tells me to cease and desist, I’m going to keep doing it.” HHH hints at the company upheaval happening in his absence. NXT goes from Black and Gold to 2.0. Trick Williams, NXT Superstar tells us how everything changed when Shawn took over. Shawn tells the talent that if he had to wrestle on television in six months like they did, he’d shit a brick. He felt a real connection with this new crew and knew he had to manage the ship. HHH comes back to Raw and SmackDown and Shawn keeps running the NXT ball. Jacy Jayne, NXT Superstar says Shawn will always tell you the truth whether you want to hear it or not. Sol Ruca, NXT Superstar says he really cares about them, and her boss is the best. Trick says Shawn told him to be great at what you do. Jacy calls Shawn his wrestling dad and Shawn corrects her to “wrestling grandpa.” We cut through Shawn joking around with the wrestlers. We also watch him filming the TikToks and laughing about it because “having the opportunity to embarrass your children never gets old.” Sol laughs about talking Shawn through TikToks. Various people tell us he truly has made the PC and NXT a family atmosphere.

October 7, 2025. NXT Showdown. Shawn talks about how so many years were about trying to be the only brand and now they’re working with TNA. Hendry tells us about TNA and the partnership to benefit both parties. Mustafa Ali, TNA Wrestler greets Shawn. Shawn remembers being in the fight of the Monday Night Wars and now how it feels for the whole business to flourish. Shawn says they have some veterans like the Hardys that the NXT crew are lucky to work with. The Hardy Boyz, TNA Superstars / WWE Legends talk about how unreal it is to be here with Shawn. Matt’s amazed at seeing Shawn giving back the way he is. Shawn says he’s still a wrestling fan and Matt laughs at how Shawn will grab his hand while watching sometimes backstage. “When he sees the highs, he shares the highs with the talent.” You can tell how much Je’Von loves Shawn in this. Shawn: “Sometimes we didn’t have people telling us, and we just want to make sure that we’re at least a generation that acknowledges this generation’s hard work in hope that they’ll do it with the next.”

Bruce knows that if you asked in 1995 where Shawn would be in 2026, he’d say hopefully teaching the future. Shawn says he has experiences to motivate people and scare them straight. He’s mended his past relationships. Bret jokes with him and says he’s matured. Hunter says Shawn moved the business forward and became one of the greatest of all-time. Taker knows that what he is doing now will be his biggest accomplishment in wrestling.

Shawn: “There are two things in this life that I care about and that is my wife and children and the WWE. If I can leave them both better off, I’ll rest easier in eternity.”

On-screen text: “Since taking over NXT in September 2021, Shawn Michaels has helped over 40 Superstars reach the main roster.” He congratulates Je’Von on his callup and tells him to come back and visit and his number won’t change. Text: “That now includes Je’Von Evans and Trick Williams.”

As credits roll, we see outtakes with his children. The last thing we see is Shawn doing his pose with his son and daughter.

Alright, thoughts. First, there’s a lot of bias personally. Shawn was the first person I called my favorite wrestler. I was the fangirl of all fangirls for that mid-90s rise. The first wrestling shirt I owned was the one-size-fits-most black and blue “all over” tee. I have a deep love for this man and his career.

“What new things could a Shawn documentary even bring after the book and the other docs,” you might ask. I asked that too. And they answered. The touching on the past is nice. The large focus on NXT PC Dad Shawn was remarkable. You’ve always gotten a sense of how much the NXT crew loves Shawn, but this will give you a wide-open look at how much Shawn loves what he is doing in 2026. NXT might not always be the best show, but the amount of talent running through that Performance Center is WILD and he’s been the one that has been making it happen over the last few years. Seeing him and his children – who work there! – is also such a feel-good moment for those of us who saw Shawn at his absolute worst.

Out of the run of Peacock “Becoming” documentaries, this is the best one by a mile. High, high recommendation to watch this.