WWE’s Best Heel Every Year During the 1990s

WWE went through three significant eras in the 1990s. The Golden Era was led by Hulk Hogan, who left in 1993. WWE went through muddy waters for parts of the New Generation Era, and the 90s ended in beauty with the Attitude Era. While there were some standout babyfaces in the ’90s, there were heels who enjoyed playing the antagonist role.

RELATED: 10 Top WWE Superstars Every Year In The 1990s

Top heels managed to make fans hate them and they performed their role as heels to perfection. The 90s were arguably the hottest time in professional wrestling. WWE took on WCW in the Monday Night Wars. Nevertheless, the greatest heels of this period managed to put fans on their backs with the best character work that made them hated.

ten
1990: Mr. Perfect


Mr Perfect & Bobby Heenan Intercontinental Champion Cropped

Mr. Perfect is one of the greatest wrestlers to ever win a WWE World Championship. Perfect was in his prime as the reigning Intercontinental Champion and Bobby “The Brain” Heenan was at his side. Perfect had a great 1990, and he should have won the Royal Rumble match, but he finished second to Hulk Hogan.

Perfect is widely considered the best Intercontinental Champion in WWE history. His 1990 was excellent and he was the best heel in WWE. He did not win the WWE Championship, but he did win the Intercontinental Championship twice that year.

9
1991: The Undertaker


Undertaker WWF Champion 1991

To Survivor Series 1990, The Undertaker made his WWE debut and three decades later retired at the same event on the exact day. The Phenom’s gong struck fear into the hearts of fans, and he was right in the thick of it as a top star in 1991. His legendary WrestleMania unbeaten streak started at Wrestle Mania 7 when he defeated “Superfly” Jimmy Snuka.

Undertaker feuded with Randy Savage and The Ultimate Warrior. Paul Bearer came on board and they became one of the greatest double acts in WWE history. However, Hulk Hogan seemed unstoppable, but that was until he met The Undertaker. The Undertaker capped off a great year by winning his first WWE Championship by defeating Hogan at Survivor Series. Undertaker’s heel work set him up to be a lovable babyface a year later and for most of his career.

8
1992: Ric Flair


Ric Flair Royal Rumble 1992 Cropped

Adding Ric Flair to WWE was a smart move. The Nature Boy wasted no time winning the WWE Championship for the first time in the 1992 Royal Rumble match. Flair never competed in a main event WrestleManiabut he should have made the Main Event Wrestle Mania 8 with Randy Savage.

Naitch was at the top of his game in 1992. Miss Elizabeth’s seductive flair that infuriated Savage was brilliant storytelling. Flair traded the WWE Championship with Savage, and he briefly took Razor Ramon under his wing. Unfortunately, Flair was no longer a main eventer by 1993, which is why he decided to join WCW.

7
1993: Shawn Michael


Shawn Michaels 1993 cropped

1993 was a sublime year for Shawn Michaels. The Heartbreak Kid entered the year as the Intercontinental Champion, and he looked comfortable in his title fights. The likes of Marty Jannetty and Tatanka failed to take the title from the Heartbreak Kid at the Royal Rumble and Wrestle Mania 9.

RELATED: 10 Games You Forgot Shawn Michaels Was In

Michaels was cocky and he was running his mouth. Therefore, he needed a bodyguard, and Diesel backed up Michaels. Yokozuna may have been the reigning WWE Champion, but Michaels’ overall combination of mic and in-ring skills was superior to Yokozuna’s. The Showstopper’s year was cut short prematurely as he tested positive for steroids.

6
1994: Owen Hart


Owen Hart King of the Ring 1994 Cropped

Unquestionably, 1994 was one of the best years of Owen Hart’s wrestling career. Bret Hart’s younger brother thrived on being the villain of the pantomime. Owen betrayed Bret in their Tag Team Championship match at Royal Rumble. Additionally, Owen upset Bret in the opener of Wrestle Mania 10​.

Sandwiched between his triumph at WrestleManiaand their WWE Championship match at Slam summerOwen won the King of the Ring tournament in 1994. The King of Harts interfered with his incredible technical skills, and although he couldn’t beat Bret for the WWE Championship, it cost him the title to Survivor Series.

5
1995: Shawn Michael


Shawn-Michaels-Royal-Rumble-1995-Cropped-3

Shawn Michaels is arguably the greatest in-ring performer to ever grace a WWE ring. The Heartbreak Kid was still a heel, and he set his sights on the WWE Championship. Michaels’ 1995 got off to a perfect start as he won the Royal Rumble match from the unenviable position of number one.

HBK challenged his former bodyguard Diesel for the WWE Title at Wrestle Mania 11. It was a quality WWE Championship that Michaels should have won, but he failed. Nonetheless, HBK’s 1995 opener was memorable and he turned face in the summer of that year.

4
1996: Steve Austin


Stone Cold Steve Austin 1996 cropped

Steve Austin’s remarkable rise in 1996 was amazing to watch. Austin’s year got off to a rocky start as he was the Ringmaster and was under the tutelage of the experienced Ted DiBiase. However, once Austin parted ways with DiBiase, Austin’s stock increased.

RELATED: The 10 Funniest Rock Stunners Ever

Austin won the 1996 king of the ring tournament, and he cut a memorable promo that set him on his way. The Texas Rattlesnake called Bret Hart who was on sabbatical, and they engaged in a memorable feud that began with a high-profile contest at Survivor Series. Austin’s mic skills are among the best in WWE history, and his matches have been phenomenal.

3
1997: Bret Hart


Bret Hart 1997 Cropped

There were a few contenders who could have been the top heel of 1997, but Bret Hart gets the nod ahead of Shawn Michaels. Excellence in execution did some of the best work of his career and he thrived as a heel. The Hitman was the face of the next generation era, but he refreshed his character by turning on his heels and reforming the Hart Foundation.

Hart was hated by fans in the United States, but fans in his hometown in Canada and the United Kingdom loved him. Bret won his fifth and final WWE Championship at the expense of The Undertaker at Slam summer. Sadly, his WWE career ended in the most shocking way possible as he was kicked out of the WWE Championship by Shawn Michaels at Survivor Series in the Montreal Screwjob.

2
1998: Mr. McMahon


The Rock WWF Champion Survivor Series 1998 Cropped

The character of Mr. McMahon was born after Survivor Series 1997, and it was a pivotal turning point that turned the tide of the Monday Night Wars. McMahon was one of the most hated men and he tried to make Steve Austin’s life hell. Some people knew Vince McMahon was the boss of WWE, but it was out in the open after that fateful night in Montreal. He recruited the likes of Mick Foley as Dude Love, Kane, and The Undertaker in an effort to end Steve Austin’s WWE Championship reign.

McMahon as a fighting boss was the perfect rival for Austin. The Austin-McMahon rivalry was epic, and fans appreciated McMahon’s shortcomings. In late 1998, McMahon formed the Corporation, and The Rock alongside McMahon took on Austin in a feud that lasted until Wrestle Mania 15.

1
1999: Triple H


Stephanie McMahon & Triple H Armageddon 1999 Cropped

Without a doubt, 1999 was one of the most pivotal years in Triple H’s career. He was popular as the leader of DX, but he had to drop DX to take it to the next level. That summer, Triple H finally achieved his goal of becoming the WWE Champion on Raw after Slam summer defeating humanity.

His new behavior was that of a main event and Triple H became The Game. Triple H feuded with The Rock, Steve Austin and Mr. McMahon in the latter part of the year. He was cold and calculated, and to his advantage, Triple H put together a DX heel. Also, to solidify his status as a certified primary participant, he married Vince’s daughter, Stephanie, in the storyline, and the McMahon-Helmsley era was born.


Triple H and Stephanie McMahon seated and in the ring.  Also posing with Vince for a photoshoot

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