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 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.

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.

13 Val Venis


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

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.

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.

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.

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.

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.

7 Razor Ramon


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

6 Rick Martel


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.

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.

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.

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.

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