Stone Cold Steve Austin may be the most popular wrestler WWE ever featured on top. Around the peak of his success in 2001, however, the unthinkable happened—Austin turned heel. The swerve went down during the main event of WrestleMania X-Seven, and the story of Austin as a heel continued through most of the year before he returned to his face persona.

Related: 5 Things The Rock Is Better Than Stone Cold At (& 5 Things Stone Cold Is Better At)

The general consensus is that Stone Cold working heel was a mistake as fans didn’t want to see it, and it may have contributed to a downturn in ratings and merchandise sales. His heel run did have its moments, though, including some standout work with and against Kurt Angle, The Two-Man Power Trip partnership with Triple H, and more.

10 Austin Regrets It

Austin McMahon WrestleMania 17

There are certain talking points that Steve Austin has returned to time and again his Steve Austin Show podcast and, more recently, his Broken Skull Sessions interview show for WWE. He talks about preferring to work heel. He also talks about how he regrets his heel turn in 2001.

Austin has gone so far as to say that he wished he’d called an audible at WrestleMania 17 itself. He indicates he could have hit a Stunner on Mr. McMahon to suggest that, though the Chairman had helped him win the WWE Championship, Austin had really manipulated McMahon to help him, but was as anti-authority as ever.

9 Vince McMahon Thought His Heat Could Overpower Austin’s Popularity

Mr. McMahon Heel

In discussing the moment of Austin’s heel turn on his podcast, Grilling JR, Jim Ross has suggested that WWE’s thinking was relatively simple. Austin was at least as, and probably more popular than The Rock, and especially so in his home state of Texas, where WrestleMania 17 took place. Nonetheless, the thought process as that the Mr. McMahon character was hated enough that Austin allying with him against The Rock would turn the crowd on him.

Related: The 10 Most Ridiculous Storylines Involving Vince McMahon

While the concept had some merit, things didn’t go according to plan. Despite Austin and McMahon working together heelishly, the turn was doomed from the start, as the crowd still cheered him. Ross and Paul Heyman scrambled on commentary to ensure that at least the fans watching from home would understand that Stone Cold was now a heel.

8 Austin Had, By Far, His Longest World Title Reign As A Heel

Austin Heel Champion

When fans think back to the Attitude Era, it’s not uncommon for images of Austin slinging the world title over head to dance through their heads. Interestingly enough, though, none of his four world title reigns rated among the longest of the 1990s or 2000s—the lengthiest among them running just 91 days.

By contrast, Austin’s first heel world title reign was nearly twice as long at 175 days. The reign felt even longer, because there was only a two-week gap of Kurt Angle reigning before Austin got the title back for two more months, for a pair of reigns that combined to eat up over 60 percent of the year 2001.

7 Kurt Angle Hoped To Reprise The Most Iconic Moment From Their Rivalry At His Hall Of Fame Induction

Kurt Angle Milk Truck

Few moments from Stone Cold’s heel run, nor of Kurt Angle’s whole career, were as iconic as when The Olympic Gold Medalist drove a milk truck to the ring to spray Steve Austin and his associates. The moment happened the night after one of Angle's best matches as a face, opposite Austin at SummerSlam, and was a fun callback to when Austin drove a beer truck to the ring two years earlier..

Angle discussed in an interview that he actually wanted to drive a milk truck on his way to the podium for his Hall of Fame induction, too. Whether it was logistics or judgment call from management, that vision didn’t come to fruition. Angle still spoke of the moment, though, and capped his speech by dumping two bottles over himself in celebration.

6 Jim Ross Rallied Against The Heel Turn

Steve Austin Jim Ross

Jim Ross tends to be one of the best respected voices from behind the scenes in wrestling. He has earned that credibility via his decades of success across promotion as a wrestling play-by-play man, but also via his real life work in powerful roles behind the scenes.

Good Ol’ JR has pulled no punches in discussing Austin’s 2001 heel turn, and specifically that he was against it. In an episode of Grilling JR, he spoke about how unlikely fans were to turn on the most popular act in the company, besides which, turning Stone Cold heel would jeopardize the popularity of the company itself. In hindsight, it’s hard to deny that Ross was right.

5 Stone Cold Wanted The Two Man Power Trip To Run Longer

Two Man Power Trip Vs. Brothers Of Destruction

One of the more captivating parts of Steve Austin’s 2001 heel run was when he teamed with Triple H as The Two-Man Power Trip. For a brief period, Austin was the WWE Champion, Helmsley was the Intercontinental Champion, and together they reigned as Tag Team Champions.

On March 16, 2021—3/16 Day—Triple H tweeted about memories of Austin. Austin replied to express his shared respect for Helmsley, noting that he wished The Two-Man Power Trip had lasted longer. Sadly, the partnership only lasted a couple months before Helmsley suffered a real life injury that derailed the story.

4 A Phone Exchange With Christian Prompted The “What?” Chant

Steve Austin What

One of the few parts of Steve Austin's months as a heel to survive past 2001 was the infamous “What?” chant. Austin bullied others by constantly interrupting what they had to say. Fans picked up on it, interrupting promos with the question for years.

Austin has discussed on his podcast as well as on The Broken Skull Sessions that it was a real life phone exchange with Christian that instigated this catchphrase. Austin asked the question repeatedly on a voicemail and found it so infectious and agitating that it felt like a perfect addition to his character.

3 Management Felt They Owed The Heel Turn To Austin

Steve Austin hits Rock with a chair at WrestleMania 17

Steve Austin has made no bones about the fact that he was not only in favor of, but campaigned for his big heel turn in 2001. He was one of the very few stars with the stroke to make such a significant change happen.

According to Jim Ross—who not only worked on commentary, but in an executive role for WWE at the time—WWE's executives felt as though they owed it to Austin to “give the turn a shot.” Unfortunately, just about everyone involved felt that that opportunity failed to pay off.

2 Part Of Austin’s Heel Turn Within A Heel Turn Reflected Reality

Austin Promo

One of the more famous sequences of events for Steve Austin 2001 saw a heel turn within his existing heel turn. After bringing back “The Old Stone Cold” to WWE fight ECW and WCW's forces, Austin would swerved his friends. He (re)turned heel to join The Alliance.

Related: The 10 Biggest Booking Errors During The Invasion

Austin provided a rationale afterward that McMahon had shown favoritism to other Superstars like Kurt Angle, and he knew that WWE was trying to bring back The Rock. The jealousy represented in the promo mirrored some of the real life insecurities Austin has subsequently spoken to, that led to him wanting a heel turn—feeling as though his old character may be stale, and soon surpassed.

1 The Only Time In History The Survivor Series Main Event Boiled Down To Rematch From That Year’s WrestleMania Main Event

Austin Rock WrestleMania Survivor Series 2001

When WWE staged the very first Survivor Series in 1987 they wanted to book Hulk Hogan and Andre the Giant, without booking a straight rematch from WrestleMania III. The team format mixed things up, besides masking Andre's physical limitations with four partners.

That original Survivor Series main event boiled down to Andre vs. Bam Bam Bigelow, rather than Hogan, though. Indeed across 35 years, only one main event ever saw the elimination tag team main event come down to the same two men who had closed WrestleMania. Fittingly, it was Steve Austin and The Rock who got that honor. Yes, they'd had one of the greatest WrestleMania main events. There was poeticism, too, to WWE's top stars of the Monday Night War headlining the first PPV after WWE beat WCW, and also closing things down when WWE beat WCW in storylines.

Next: Why Stone Cold's Exit From WWE Hurt Them Worst (& Why The Rock's Did)