Top 15 Playboys In Wrestling History

If you want to succeed as a wrestler, you’ve got to have the look. Apart from many other components, the superstars of the squared circle pride themselves on looking good both in and out of the rin

If you want to succeed as a wrestler, you’ve got to have the look.

Apart from many other components, the superstars of the squared circle pride themselves on looking good both in and out of the ring. Glorious costumes, expensive cars and fancy haircuts are the norm for some of the best looking men in professional wrestling, while others brag about their riches with charisma and charm.

In most cases, heels project themselves as the biggest playboys, flaunting their money in the faces of their adversaries and the onlookers. Other wrestlers, who are actually loved by their peers, get by with being cute youngsters and kill with kindness.

Playboys have been an essential part of wrestling since the early days, and the rich, cocky characters are still being used to this day. In most cases, the gimmick transcends into real life, where numerous wrestling superstars live life no different than their characters.

While many fans focus on the scantily clad women of pro-wrestling (with a group of them gracing Playboy covers of the past), it’s time to run down the list of the hottest playboys in wrestling history.

Without further ado, here are the top 15 playboys that have graced the wrestling ring:

15 Tyler Breeze


NXT’s resident “Prince Pretty” has done enough to warrant a spot on this list, being the most arrogant playboy in wrestling today.

His promos are great to watch, since his faux voice brings a comedic element to his egotistical personality. Drawing inspiration from a number of playboys from the past, the beautiful Breeze excels in doing it right.

14 Alberto Del Rio


He doesn’t show up in glamorous clothes or beautiful cars anymore in his new wrestling ventures, but there was once a time when Alberto Del Rio was the richest and most hated wrestler on the WWE roster.

Coming into his own after winning the Royal Rumble Match in 2011, the Mexican wrestler was already shoving his accomplishments down everyone’s throats, whether they were in the squared circle or otherwise. Hiring a mouthpiece (Ricardo Rodriguez) and coming to the ring with a different car every night surely cost him a pretty penny.

13 Val Venis


One would imagine Val Venis made enough money in the adult entertainment business to be considered a playboy.

It was hard to distinguish if Venis spent top dollar on clothes, considering he wore a towel more often than not. Nevertheless, Venis had multiple love affairs, including Marlena, Ryan Shamrock and Mrs Yamaguchi-san.

12 Paul Orndorff


One half of the lesser-known WCW tag team Pretty Wonderful, “Mr. Wonderful” himself had major success in WWE as a main eventer before his time in the South.

Paul Orndorff didn’t brag about his riches more than he dished out the punishment. He was an outstanding presence in the ring, complete with a muscular physique his admirers could only dream of having.

11 The Fabulous Freebirds


Buddy Roberts and Terry Gordy weren’t known for their looks, but when it came to Michael Hayes and Jimmy Garvin, they truly made their followers woozy, and it’s hard to just pick one playboy out of the two.

The Fabulous Freebirds had some of the most vicious matches in the 1980s, yet they stayed pretty for their fans, living the life of the rock stars they depicted.

10 Buddy Rose


Brutal in the ring and arrogant on the mic, Buddy Rose didn’t exactly have the best body in the business (he gained an umpteen amount of weight towards the end of his career). The blond competitor, managed by the likes of Bobby Heenan and The Grand Wizard, wrestled for a few decades and always made sure to keep his charm.

His nickname was “Playboy,” after all.

9 Buddy Rogers


The original “Nature Boy” was a joy to watch in the ring during his heyday, bringing out the best in his opponents and carried matches more often than he should have.

The first-ever NWA United States Champion was a striking presence, influencing many of the greats such as Ric Flair and Triple H, to name a few. He was also the first wrestler to hold both the NWA World Heavyweight strap, along with the WWWF World Heavyweight Championship.

8 Randy Savage


The most extravagant and vibrant outfits were designed for the “Macho Man,” and Randy Savage surely fit the part when he entered arenas across the globe. He was one of WWE’s most revered kings, able to dazzle in the ring and on the mic too.

His personality was as colorful as his suits, and he could go down in history as having the best wrestling wardrobe ever.

7 Razor Ramon


When vignettes aired promoting the slicked-back greaser Razor Ramon, audiences caught a glimpse of something special behind all that rudeness.

Sporting gold and imitating Tony Montana, the genetically gifted Scott Hall simply oozed machismo in his daring dress shirts and dreamy convertibles. Observers soon started to grow fond of the “Bad Guy,” without him having to drop his mean streak.

6 Rick Martel


The French Canadian didn’t brag about his riches as much as he constantly reminded everyone he was a model. Spraying arrogance down the aisle and into the faces of his opponents, the “Model” made it easy to dislike him. He was a gifted athlete, complete with the chiseled look and impressive body, but his holier-than-though attitude made stomachs turn.

5 Rick Rude


“Ravishing” Rick Rude, known as one of the toughest guys in the world of wrestling, resembled an escort more than he did a wrestler. When the buff mischief-maker made his way to the ring, he blew kisses galore, and judging by the plethora of smiling girls WWE filmed while he cut his promos, he had the shtick down pat.

Flamboyant robes, a thick mustache sitting on top of a big smile and tights with the faces of his adversaries smacked on his bottom was Rude’s distinctive look, and if you ask anybody who graced the ring with him, they’d tell you he was one of the best.

4 Ted DiBiase


One of the most hated heels in the history of the business, Ted DiBiase became a household name as the “Million Dollar Man.” The tall, handsome wrestler wore simple colors like black and white when he wasn’t donning green.

The richest wrestler on this list was also incredibly obnoxious, which made him despised in many circles. He did his job well, though, always looking spectacular while buying out his competition, and had his bodyguard Virgil as muscle to protect him.

3 The Rock


What would this ranking be without the “Most Electrifying Man In Sports Entertainment?”

The Rock didn’t have much sex appeal as Rocky Maivia, but when he transformed into the “Great One,” $800 dollar shirts and carefully chopped sideburns surely did the trick.

Never one to shy away from flirting, The Rock hit on the likes of Lilian Garcia and Trish Stratus when he wasn’t laying the smackdown on his opponents. To this day, Dwayne Johnson isn’t only at the top of the list of most grossing actors; he’s also still one of the most desirable heartthrobs in all of Hollywood at 43 years old.

2 Shawn Michaels


When Shawn Michaels put Marty Jannetty’s head through The Barber Shop window, the “Heartbreak Kid” was born.

He traded his leather jacket for detailed vests and tights, complete with jewelry and a mirror Sensational Sherri would hold up in order for him to look at himself. Michaels went on to great success in the sports entertainment world as a brash, cocky youngster who ticked off more compatriots than he should have when he wasn’t thrusting his hips and singing along to his “Sexy Boy” theme. He also earned himself a spread in Playgirl.

At least he backed it up.

1 Ric Flair


It’s easy to despise the rich man, but Flair was one of a kind; the true definition of someone you loved to hate.

“Nature Boy” bragged about being with several women, his elite methods of transportation and wore suits that would make a stylist melt. Thousands of fans have cut promos in their bathrobes in front of their mirrors because of him, trying to mimic his every move.

While Flair wasn’t the first “Nature Boy” and is often accused of gimmick infringement, he had the in-ring skills and natural persona to set him apart from the rest, possessing a one-of-a-kind style.

Throughout the course of his illustrious career, he never let down when the time came to soak in a crowd, with his instinctive character taking over to let everyone know how much of stud he was.

He’s probably wrestling’s most relentless philanderer, too.

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Top 15 Playboys In Wrestling History