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Ranking Ric Flair's 5 best WWE WrestleMania matches 

The Nature Boy is arguably the greatest professional wrestler in the history of the business
The Nature Boy is arguably the greatest professional wrestler in the history of the business
Owen Churchill

Ric Flair is considered by many to be the greatest professional wrestler of all time. The Nature Boy is a two-time WWE Hall of Famer and 16-time World Heavyweight Champion.

Despite spending the majority of his illustrious career outside of WWE, Ric Flair has competed at six WrestleMania events.

Ric Flair's WrestleMania opponents read as a who's who of WWE legends, icons, and future Hall of Famers. The flamboyant style and profile nature of Ric Flair was always a perfect match for the pageantry of The Grandest Stage of Them All.

Let's take a closer look at Ric Flair's five best WWE WrestleMania matches.


#5 Ric Flair vs. Bobby Lashley vs. Finlay vs. Matt Hardy vs. Shelton Benjamin vs. Rob Van Dam - Money in the Bank Ladder match (WWE WrestleMania 22)

Ric Flair was involved in some incredible moments during the Money in the Bank ladder match at WrestleMania 22
Ric Flair was involved in some incredible moments during the Money in the Bank ladder match at WrestleMania 22

WWE WrestleMania 22 saw Ric Flair step outside of his comfort zone to say the least. At 57 years of age, The Nature Boy was still an active in-ring WWE performer chasing his historic 17th World Heavyweight Championship.

To earn a future WWE World Championship opportunity, Ric Flair qualified for the Money in the Bank ladder match at WrestleMania 22. High-risk gimmick matches such as ladder matches were not in Flair's wheelhouse. But he was steadfast in reaching the mountain top one more time before he retired from in-ring action.

After a frantic start to the match, Flair found himself climbing a ladder in the middle of the ring, attempting to grab the Money in the Bank briefcase suspended above the ring. However, The Nature Boy was met by Matt Hardy, who superplexed the Flair off the 20-foot ladder, sending the icon crashing to the canvas.

The WWE Universe in attendance was in shock at the carnage they had just witnessed. Ric Flair was quickly attended to by WWE officials and medical personnel who ushered The Nature Boy out of the ring and backstage for further medical treatment.

Ric Flair reappeared in the closing stages of the match, attempting to retrieve the briefcase. But he was ultimately unsuccessful as the match was eventually won by Rob Van Dam.

#4 Ric Flair, Batista and Randy Orton vs. The Rock & Mick Foley (WWE WrestleMania XX)

Evolution faced off against The Rock N' Sock Connection at WrestleMania XX
Evolution faced off against The Rock N' Sock Connection at WrestleMania XX

WrestleMania XX saw WWE legend Mick Foley return to the ring for the first time in four years after his previous retirement in 2000.

In the months prior, Mick Foley had been feuding with Evolution's Randy Orton on WWE television. Orton had begun referring to himself as "The Legend Killer," attacking WWE legends and Hall of Famers on a regular basis. This included spitting in the face of Mick Foley, calling the hardcore legend a coward.

The feud between Orton and Foley led to a 3-on-2 handicap match at WrestleMania XX in which Randy Orton teamed up with Evolution teammates Ric Flair and Batista to face off against the legendary tag team of Mick Foley and The Rock.

The match marked the first time the Rock N' Sock Connection had teamed up for several years in WWE.

The match was an absolute joy to watch, especially the interactions between The Rock and Ric Flair. A classic WrestleMania moment saw The Nature Boy attempt to hit The Great One with his own version of The People's Elbow. Flair executed his own trademark strut before The Rock leaped to his feet to cut off The Nature Boy and do a strut of his own.

Evolution eventually walked out of WrestleMania XX victorious as Randy Orton pinned Mick Foley after hitting the hardcore legend with an RKO to gain the decisive pinfall.

#3 Randy Savage vs. Ric Flair (WWE WrestleMania VIII)

"Macho Man" Randy Savage defeated Ric Flair to become WWE Champion at WrestleMania VIII

WrestleMania VIII saw Ric Flair make his WrestleMania debut as WWE Champion in a featured match against "Macho Man" Randy Savage.

The year prior in 1991, Ric Flair left WCW after a contract dispute with the company's President Jim Herd. Ric Flair reportedly refused to take a pay cut and be demoted to a lesser role in the promotion, despite being its top star. This led to Jim Herd firing Ric Flair, who was the WCW World Heavyweight Champion at the time, and vacating the title.

This allowed Ric Flair to sign with WWE. The Nature Boy made his WWE debut in August, managed by both Bobby "The Brain" Heenan and Mr. Perfect. Only a few short months later, Ric Flair won the 1992 Royal Rumble match to win the vacant WWE Championship after entering the match in the number 3 position.

Flair then entered a feud with Randy Savage. The storyline centered around Ric Flair alleging he was involved in a prior relationship with Miss Elizabeth, who was Savage's wife at the time. This led to a match between Flair and Savage at WrestleMania VIII for the WWE Championship.

Ric Flair and Randy Savage battled it out in a brutal and physical match. At one point Flair violated WWE's "no blood" policy, intentionally blading on camera. This caused Flair to be fined several thousand dollars.

The Macho Man eventually got the victory over The Nature Boy, claiming the WWE Championship in the process. Flair would return to WCW the following year and would not compete in another WrestleMania match for ten years.

#2 The Undertaker vs. Ric Flair (WWE WrestleMania X8)

Ric Flair competed in his first WrestleMania match in 10 years against The Undertaker at WrestleMania X8
Ric Flair competed in his first WrestleMania match in 10 years against The Undertaker at WrestleMania X8

WWE WrestleMania X8 saw Ric Flair compete in his first match at The Show of Shows in 10 years against The Undertaker.

WWE famously purchased rival WCW in March 2001. On the final episode of Monday Nitro, Ric Flair wrestled long-time rival Sting in the main event. Eight months later, The Nature Boy made a shocking return to WWE by appearing on Monday Night RAW for the first time in eight years.

Ric Flair revealed that he had become the kayfabe co-owner of WWE after purchasing Shane and Stephanie McMahon's stock in the company to a consortium headed by The Nature Boy.

Heading into WrestleMania X8, Ric Flair began feuding with The Undertaker on WWE television after Flair cost Big Evil his match against The Rock at No Way Out.

Initially, The Nature Boy refused to fight The Undertaker. However, after Undertaker attacked several of Ric Flair's friends and family, The Nature Boy accepted The Undertaker's challenge for a match at WrestleMania X8.

The match between the two WWE legends was physical and stiff, with The Undertaker's vicious offense causing Ric Flair to bleed profusely. The match also saw a brief cameo from Flair's former Four Horseman teammate Arn Anderson who hit The Undertaker with a Spinebuster in a memorable WrestleMania moment.

However, The Undertaker was once again able to regain control and defeated Ric Flair after putting The Nature Boy down with a Tombstone Piledriver. This also extended The Undertaker's WrestleMania undefeated streak to 10-0.

#1 Ric Flair vs. Shawn Michaels (WWE WrestleMania XXIV)

Ric Flair competed in his final WWE match against Shawn Michaels at WrestleMania XXIV
Ric Flair competed in his final WWE match against Shawn Michaels at WrestleMania XXIV

WrestleMania XXIV saw Ric Flair compete in his final in-ring match as an active WWE Superstar before his retirement.

After a brief hiatus from television, Ric Flair returned to Monday Night RAW in November 2007 to address rumors surrounding his future as an in-ring performer. The Nature Boy proclaimed, "I will never retire", much to the joy of the WWE Universe.

However, Mr. McMahon disagreed, making the edict that the next singles match Ric Flair lost would mean The Nature Boy would be forced to retire. This then led to Ric Flair winning several "career-threatening" matches over the next few months against the likes of Randy Orton, Triple H, Umaga, Mr. Kennedy, and Mr. McMahon.

After being announced as an inductee into the WWE Hall of Fame Class of 2008, Ric Flair challenged Shawn Michaels to a match at WrestleMania XXIV. The Heartbreak Kid reluctantly accepted, knowing if he defeated Flair, he would be retiring his idol.

Ric Flair and Shawn Michaels faced off in one of the greatest matches in WWE history at WrestleMania XXIV. Michaels eventually defeated The Nature Boy, mouthing "I'm sorry, I love you", before hitting Ric Flair with Sweet Chin Music and retiring the greatest wrestler of all time.

Edited by Amar Anand

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