Without question, wrestling has been a major part of my life since I was a kid. As such, watching Monday Night RAW was appointment television for me. Furthermore, the Attitude Era (1997-2002) in the then-WWF was the likes we will never see again. Before diving into the list, I want to hand out a few superlatives concerning the Attitude Era.

Top Heel: Vince McMahon 

Mr. McMahon is the only answer here. At the start of the era, he screwed over arguably the top babyface in the company in Bret Hart at the 1997 Survivor Series in Montreal. It is referred to as the Montreal Screw Job. It was here where his heel persona was born. McMahon’s handprints are all over the Attitude Era.  

Whether it was his legendary feud with Stone Cold Steve Austin or stepping into the squared circle himself, he was the most hated figure in the business. Plus, being the top authority figure only made him loathed that much more. In essence, he was the Joker to everyone else’s Batman. 

Top Female: Chyna 

Firstly, Chyna was a trailblazer in every sense of the word in this era. She was the menacing bodyguard in the faction Degeneration-X (DX) but she would soon become more than that. Most women were unfortunately not seen as equal to their male counterparts in the Attitude Era. Chyna made sure to change all of that.  

She was the first female to be a participant in the King of the Ring Tournament in June 1999 and the Royal Rumble Match. Chyna achieved the latter feat in 1999 and 2000. She was also the first woman to hold the Intercontinental Championship. Chyna achieved this on two separate occasions, also in 1999 and 2000. 

Without Chyna, we probably would not have the likes of Beth Phoenix, who is dominant in her own right. Hopefully, Chyna will take her rightful place in the WWE Hall of Fame.  

Now, onto the list. 

5. Kurt Angle 

Firstly, he won a gold medal in the 1996 Olympics with a broken neck. This cannot be stated enough when we talk about Kurt Angle. In November 1999, he made his debut and, by February 2000, he was the European and Intercontinental Champion. He had a meteoric rise in this era, which was capped off by defeating The Rock in October 2000 at the pay-per-view No Mercy for the WWF Championship. By the way, he fought some up and comer named John Cena to initiate another era: Ruthless Aggression 

Angle made the seamless transition from an amateur wrestling career to the pro wrestling industry. He fought the likes of the Undertaker, Triple H, and the aforementioned The Rock within a little over a year of his debut. He showed people that you can be a newcomer and become an overnight success. This era propelled him into being a WWE Hall of Famer: It’s True, It’s True.  

4. The Undertaker 

The first thing to remember is whenever you compile a list of the greatest wrestlers of their generation, The Undertaker is a name that must be mentioned. If not, throw out the list because it is not a list. I can assure you that he fought everyone who was there to fight in this era. He had a long-standing feud with Kane, who was a star in this era in his own right.  

He fought Mick Foley, aka Mankind (an honorable mention on this list) in Hell in a Cell match. This was one of the best matches of the era. Seeing him toss Foley from atop the cage is an iconic moment. However, in 1999, he formed The Ministry of Darkness, and it was a game-changer. 

To begin, The Ministry of Darkness kidnapped Vince McMahon’s daughter, Stephanie, keeping her hostage in the boiler room of an arena. Then, sacrificed Ken Shamrock’s sister the following week in front of a live crowd. Next, The Undertaker attempted an unholy wedding with Stephanie McMahon but was foiled. Ultimately, The Ministry unified with The Corporation, forming The Corporate Ministry.  

After leaving for eight months due to injuries, he returned with a new persona: The American Badass. This character was someone who was not a babyface but certainly not a heel. Here, The Undertaker is a guy in jeans with a bandana, riding a motorcycle with shades on ready to kick butt and take names later. His change from babyface to heel to tweener defined The Undertaker in this era.  

3. Triple H 

Triple H spent the start of the Attitude Era as the unquestioned leader of the faction DX. Afterward, he became The Game, transitioning into the main event wrestler, winning several WWF Championships in addition to being an integral part of the McMahon-Helmsley Era storyline. 

When the Attitude Era peaked around the middle of 1998, DX was as hot as anyone in the company. There were kids, myself included, going around chopping crotches while exclaiming “suck it” whenever possible. Anyways, with Triple H’s ascension to the top of the stable, it was must-see television.  

As a singles wrestler, Triple H upped his game. He had a strong line of first-rate matches throughout 2000 and 2001. Whether it was the Street Fight for the WWE Title versus Cactus Jack at the Royal Rumble in 2000 or the Iron Man Match for the WWE Title versus The Rock at Judgment Day in 2000, he was a workhorse. 

2. The Rock 

Everyone could smell what The Rock was cooking as he became one of the biggest stars of the Attitude Era. After winning the WWF Championship win at Survivor Series 1998, he rose speedily, becoming a top heel to work next to Austin at one of the foremost superstars in WWF. Specifically, both men fought, unequivocally, the best match in the Attitude Era at WrestleMania 17, or X-7 as it was denoted.  

When it comes to the microphone, The Rock’s promos were legendary. He frequently poking fun at his opponents in some of the most hilarious moments of the Attitude Era. You can check out his greatest moments right here. He would become a multiple-time WWF Champion, facing superstars like Austin, Mankind, The Undertaker, and Triple H. Along with his second-to-none charisma, he launched his Hollywood career with films such as The Scorpion King, Walking Tall, and Fast Five. His career can be summarized in one word: electrifying.  

1. Stone Cold Steve Austin

How could I put anyone else in this spot beside the Texas Rattlesnake? If you had to put a face on the Attitude Era, it would be Stone Cold Steve Austin. He meant just as much to this era inside the ring as out of it. In the ring, he fought the likes of every single wrestler I mentioned on this list to others like Kane, Shawn Michaels, and Rikishi, winning several titles along the way. 

Outside of the ring, Austin was the ultimate antithesis of what we saw in superstars at the time. He was in your face, chugging beer like it is going out of style and showing folks they were number one with his middle finger. As I have noted previously, his feud with Vince McMahon saved the WWF. They were losing for months against their rival, WCW. The Austin/McMahon feud is the greatest feud not just of the Attitude Era, but in the company’s history. 

The defiance of the Rattlesnake versus the evil corporate boss in McMahon made for great television. Growing up, many kids and some adults could relate. Fans saw the evil boss as their parents, teachers, or, in the case of adults, their bosses. Austin was the driving force of this era.  

Every wrestler and person mentioned in this piece played a pivotal role in making the Attitude Era as it was. That’s the bottom line because I said so. Also, if you’re not down with that, I got two words for you. For those two words, go here

Who Is Your Top Five in the Attitude Era? 

Before you give me a Stone Cold Stunner or an Angle slam, what are your thoughts on this top five? Let me know on my Twitter and Instagram. Furthermore, check out all of the amazing content we have here at Belly Up Sports. If not, a Pedigree might be imminent.  

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LaDarius Brown


    That was good but no love for E&C,Y2J, or the Hardy’s?

      For the purpose of this list, I chose singles competitors. I love these tag teams. As for Y2J, he’d be in my Top 10 of the Attitude Era.

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