The feud between two generational stars, combined with the importance of both being at the forefront of the Ruthless Aggression Era, the rivalry of Randy Orto vs Shawn Michaels was seemingly a dream match scenario. In 2007, this scenario became a reality as they collided in a bitter feud that included matches for the WWE Championship that spanned nearly a whole calendar year. 

At Wrestlemania 23, John Cena defeated Shawn Michaels in the main event. Afterwards, both Michaels and Randy Orton wanted the opportunity to face Cena at the next pay-per-view, Backlash. On an episode of RAW, Michaels and Orton squared off, and their match ended in a draw when both shoulders were down as the referee counted to three. The following week, Edge proclaimed to be named the number one contender to HBK and Orton’s disbelief, who were both claiming to be the rightful contender. A match was then announced for Backlash 2007 where John Cena would defend his WWE Championship against all three men in a Fatal 4-Way.

Ultimately, Cena retained the WWE Championship after John fell on Orton for the pinfall after receiving Sweet Chin Music.

Tensions continued to escalate between Randy Orton and Shawn Michaels after Backlash, and a match was made between the pair for Judgement Day. In the weeks leading up to Judgment Day, the Heartbreak Kid suffered a legitimate knee injury. At Judgment Day, to cover for Michaels's inability to work, Orton blindsided him backstage. The Legend Killer stood in the ring and declared himself the winner, only for Michaels to come out stumbling and make his way into the ring. The match started with Michaels getting the upper hand, but when he attempted the Sweet Chin Music, Michaels collapsed. The referee called for the bell as Michaels could not stand to continue. Orton took advantage of Michaels being down and delivered a punt kick straight to the head of Michaels.

This would lead to Michaels being written out of WWE television for the next few months following the vicious attack from Orton. While Michaels was out of action, Randy Orton became involved in a feud with John Cena over the WWE Championship.

After coming up short at Summerslam, Orton gained an immediate rematch at No Mercy. Unfortunately, on the road to No Mercy, Cena suffered an injury, which led the WWE Championship to become vacant.

At No Mercy, Randy Orton defeated Triple H in Last Man Standing match to become WWE Champion for the second time.

The next evening on RAW, Randy Orton held a championship celebration in front of the entire roster. This moment was interrupted by Shawn Michaels, who officially returned to television. During a standoff in the ring, HBK delivered Sweet Chin Music to Orton to send a message that their rivalry was far from resolved.

With Cyber Sunday fast approaching, it was decided that Randy Orton would defend his WWE Championship against the fan’s choice through a public vote. The challengers were Shawn Michaels, Mr. Kennedy and Jeff Hardy.

On RAW leading up to the event, Michaels hit the champion with a Sweet Chin Music on three separate episodes in a row.

On Cyber Sunday, HBK received 59% of the vote from the public, which led him to be chosen as Randy’s opponent. As the Heartbreak Kid had the advantage, he was preparing to execute Sweet Chin Music, but Orton countered with a low blow. This disqualification meant that Orton successfully retained his championship. 

The next evening on Monday Night RAW, Shawn Michaels requested a rematch with Orton after the way their match ended on Cyber Sunday. RAW General Manager William Regal announced that at Survivor Series, Shawn Michaels would be granted his rematch with Randy Orton but the Sweet Chin Music would be banned. In another stipulation, if Orton got himself disqualified, the WWE Championship would change hands. 

Their match at Survivor Series marked an official conclusion to this bitter rivalry. Shawn Michaels gained the upper hand, but HBK continued to be tempted to hit his famous Sweet Chin Music only to stop realizing it was banned. Capitalizing on the hesitation, Orton delivered an RKO and pinned Shawn Michaels to end their feud while retaining his WWE Championship.

When asked by WWE.com in 2014, “Are there overlooked matches from your careers that you hope will find a new life on WWE Network?” one of Shawn’s choices was this specific match against Randy.

Another one that I think about is the one I had with Randy Orton where I couldn’t use Sweet Chin Music [from Survivor Series 2007]. Not being able to use my signature move caused me to wrestle in a way that I didn’t traditionally wrestle. It’s one of those things that might mean more to me than anybody else, but the psychology going into that one was pretty cool.

Over time, Randy Orton noticed the similarities between himself and Shawn.

“I was lucky to have some great men in the locker room, kind of see how they went about life and how they were with their kids. I got to see Shawn Michaels, who, on all accounts was a complete as*hole. And when I met him I even thought he was a pr*ck. But, I saw the change and I heard the stories… And I feel like, it’s kind of funny, the same thing kind of happened to me. Kind of. You know, it’s part of the journey. I think my legacy is the longevity,”

The intricate rivalry between Shawn Michaels and Randy Orton feud is often forgotten amongst each other’s career highlights. Still, their storytelling in their matches was superb and contained compelling twists with the blow-off match at Survivor Series being their finest moment.

Never underestimate the power of a good story.