WWE's 15 Primetime Playboys

WWE's 15 Primetime Playboys

playboy (pley - boi) n.: a man who lives a life devoted chiefly to the pursuit of pleasure  

WWE has seen its fair share of eccentric personalities and larger-than-life Superstars. Yet when it comes to being a playboy — the “stylin’ and profilin’” sort, that is — only a select handful of competitors can rightly hold claim to such a title, and personify the lifestyle that accompanies it.

Today, Alberto Del Rio reigns supreme as WWE’s resident aristocrat, arriving to his matches in luxury automobiles worth hundreds of thousands of dollars, and entering the ring to the sound of his own, personal ring announcer. Del Rio is literally worth a fortune, and his elitist attitude has often put him at odds with other Superstars of lesser means.

Then again, when you’re talking about WWE’s all-time playboys, is Del Rio simply standing on the shoulder of fine linen suit-wearing giants?

Kick back with that stack of hundred dollar bills and see where WWE.com The Mexican Aristocrat ranks among the most legendary playboys in WWE history.


Shawn Michaels

Today, Shawn Michaels is remembered as a legend among WWE legends, but at one time he was better known around these parts as "The Heartbreak Kid."

And with good reason.

Everything Michaels did in the early days of his storied career, from his flamboyant entrances to his in-ring swagger, defined what it was to be a playboy.

For over two decades, HBK has entered arenas the world over to "Sexy Boy," arguably the most playboy-like theme song in WWE history. "Sexy Boy" says so much about Michaels’ charm and charisma that there hasn’t been a Superstar so intimately connected with his entrance music since the first time those familiar chords were struck and "The Heartbreak Kid" swaggered into an arena.

Speaking of entrances, one of Michaels’ best playboy moments came at WrestleMania XI. For his match against WWE Champion Diesel, HBK had planned to enter the arena with the beautiful Pam Anderson on his arm. However, "Big Daddy Cool" stole HBK’s thunder and escorted the Baywatch beauty down the ramp.

Not to be outdone, HBK responded in typical playboy fashion, arriving with bombshell Jenny McCarthy by his side instead!

For those cocky, confident early days, "The Heartbreak Kid" (super) kicks off this list of WWE’s greatest playboys.


"The Model" Rick Martel

WWE's 15 Primetime Playboys

He may not be the No. 1 playboy in the history of WWE, but "The Model" Rick Martel has an extravagance that no one else on this list can claim. Considering the company he finds himself among, that’s saying something.

What sets Martel apart is the fact that he had his very own brand of cologne, an achievement he shares with men like Hugo Boss, Ralph Lauren and Guccio Gucci.

Martel appropriately dubbed his cologne "Arrogance," and he would spray it in opponents' eyes to score cheap victories with very expensive cosmetic product. Anyone willing to carry around a pink bug spray canister filled with cologne was certainly not lacking in the self-confidence department, so it’s impossible to keep “The Model's" scent from permeating this list.


Val Venis

WWE's 15 Primetime Playboys

It’s safe to say that Val Venis exemplified WWE’s Attitude Era.

Venis was a renowned woman-stealer, a character quirk that certainly didn’t endear him to other Superstars. What it did do, however, was make Venis a living, breathing example of a true playboy.

Venis’ womanizing ways would also present him with a title opportunity.

In early 1999, Intercontinental Champion Ken Shamrock was irate at Venis because of the Superstar’s “interest” in Shamrock's sister, Ryan. The two chose to settle their score inside the ring, a decision that would cost Shamrock his title. With the help of special guest referee Billy Gunn, Venis scored an opportunistic victory over Shamrock to become the new Intercontinental Champion.

Venis would go on to lose the title just one month later, but he lost interest in Ryan long before that, dumping her just days after defeating Shamrock.


"Dashing" Cody Rhodes

WWE Hall of Famer Dusty Rhodes said that his son, Cody, is "the most naturally gifted athlete since Shawn Michaels." Aside from his obvious in-ring ability, the grandson of a plumber is also known for his displays of vanity – a trait that, while probably not something to emulate, definitely gets his name on this list.

Cody’s narcissistic roots trace back to a defining moment in his career. In 2010, Rhodes was voted "Most Handsome Superstar" by WWE’s Divas in a WWE.com poll. Soon after, Cody added the prefix "Dashing" to his name, and berated the WWE Universe for not meeting his personal hygienic standards.

He would drop his moniker after suffering an injury at the hands of Rey Mysterio. After that match, Rhodes started donning a protective mask, which served to bring out an extremely bitter, self-conscious side to the Superstar's personality. 

Rhodes would further elevate his vainglorious ways when he started going so far as to hand out paper bag masks to members of the WWE Universe that he felt needed a makeover.


Dolph Ziggler

WWE's 15 Primetime Playboys

It’s impossible to not notice Dolph Ziggler when he enters a WWE arena. When his music hits, it’s proceeded by bleach-blonde hair, a hot pink shirt, sunglasses worn backwards and a whole lot of attitude.

As WWE’s resident "Showoff," Ziggler drips with confidence, both inside and outside the ring.

Whether he’s antagonizing WWE’s finest on Monday Night Raw or laying a verbal smackdown to lesser beings on his hit YouTube show, "WWE Download," Ziggler backs up all his talk with an impressive array of moves inside the squared circle.

Escorted wherever he goes by Vicki Guerrero, Ziggler talks the talk and walks the walk of a true WWE playboy.


The Great Khali

What would a list of WWE’s playboys be without The Punjabi Playboy himself? Known the world over for his massive size and strength, The Great Khali has made his impact felt since his first day in WWE.

However, that sort of stuff doesn’t earn one a spot on this particular list.

Certainly, in-ring dominance certainly plays a part in being a true WWE playboy. Yet it’s the wildly popular "Khali Kiss Cam" that endeared the giant to the masses, and has since assured Khali his rightful place next to the greatest playboys ever.

When that familiar, soulful music filled the arena, fans knew exactly what was coming. A camera would sweep through the WWE Universe and zero in on one lucky lady who would be invited inside the ring. Once there, it was time to pucker up for The Punjabi Playboy, who, as the giant’s older brother, Ranjin Singh, reminded the WWE Universe on a weekly basis, was adored by women all over the world.

The No. 1 playboy in WWE history? No. The biggest? Without question.


"Mr. Perfect" Curt Hennig

WWE's 15 Primetime Playboys

While all the Superstars on this list can rightfully lay claim to the title of playboy, only one can claim perfection.

WWE Hall of Famer Curt Hennig did everything perfectly — from his in-ring ability that featured an array of devastating and graceful maneuvers to his meticulous appearance.

In a series of memorable video montages — including one featuring baseball Hall of Famer Wade Boggs — "Mr. Perfect" proved his moniker accurate by performing incredible feats of athleticism, thus cementing his place as one of the greatest athletes WWE had ever seen.

Claiming perfection is one thing; backing that claim up is another entirely, and for that, “Mr. Perfect” is a must-have on our list.


"Playboy" Buddy Rose

British Bulldog vs. "Playboy" Buddy Rose: November 24, 1990

Davey "Boy" Smith battles Buddy Rose at Madison Square Garden on November 24, 1990, with Smith struggling to overcome Rose's formidable advantage in size.

Buddy Rose was such a cool cat that he actually went by the nickname, "Playboy." And, like the saying goes, "the name makes the man."

Rose is remembered for classic rivalries as a singles competitor with "Rowdy" Roddy Piper and Jimmy "Superfly" Snuka, and later on, The Playboy became embroiled in an intense rivalry with an up and coming tag team calling themselves The Midnight Rockers.

But it was Rose’s eccentric personality that sets him apart and cements his place on this list of all-time playboys. Rose flaunted the fact that he made lots and lots of money, and constantly reminded the WWE Universe that his lifestyle was but a dream to the fans in attendance.

Rose was also known for his vanity, as evidenced later on in his career, when the 300-pounder would make a point to correct the ring announcement of his weight, proclaiming instead that he was a "slim, trim 217 lbs."


"Ravishing" Rick Rude

WWE's 15 Primetime Playboys

"Ravishing" Rick Rude may not have been able to compete with the likes of Alberto Del Rio in terms of sheer wealth. But, honestly, who can?

What puts Rude in the company of other primetime playboys is his way with the women of the WWE Universe.

Rude was a playboy both coming and going, entering arenas in a flowing robe before taking to the mic. Rude would cut off his own music and memorably tell the crowd, "I want all you fat, ugly [fill in local insult here] to keep the noise down while I take my robe off and show the ladies what a real sexy man looks like. Hit the music!" The aptly-named Rude would then disrobe, and add in a little shake for good measure.

It didn't end there. Following every victory, his manager – the legendary Bobby "The Brain" Heenan – would pick out the most beautiful female fan in the crowd and invite her to the ring for a little lip service with The Ravishing One himself.

If that doesn’t scream "playboy," then we don’t know what does.

Rude may have gone too far one night in 1988, however, when he chose a woman named Cheryl as his latest "lucky" lady. Cheryl, as it turned out, was Cheryl Roberts, wife of Jake "The Snake" Roberts. Rude’s playboy ways embroiled him in a venomous, memorable rivalry with Roberts – one that reached its apex when Rude just couldn’t help himself and wore tights with Cheryl’s face painted on them.

Sure, sometimes the playboy mentality got Rude into trouble, but as Theodore Roosevelt said, "If you could kick the person in the pants responsible for most of your trouble, you wouldn't sit for a month."


The Godfather

WWE's 15 Primetime Playboys

A staple of the Attitude Era, The Godfather may very well have had the most memorable entrance of any Superstar in the 1990s.

Although it can be said that every man on this list had a way with the ladies, The Godfather was followed by a veritable trainload of them to every match in which he competed! Escorted to the ring by a bevy of dancing beauties, The Godfather’s outlandish outfits and over-the-top attitude left an indelible mark on the WWE Universe.



WWE's 15 Primetime Playboys

Rock star looks, a cult following and uncanny in-ring ability make WWE Hall of Famer Edge a top-flight playboy. Oh, yeah, and he had a way with the ladies, too. So proficient was Edge in the language of love that he became known as "The Rated-R Superstar."

Edge’s high-profile relationships with Lita and, later, Vickie Guerrero, leave just as big a mark on the memory of the WWE Universe as his spear off the ladder at WrestleMania X-Seven.

While he may not top this list of all-time playboys, one moment in particular stands out as arguably the most playboy move in WWE history. In Edge and Lita’s infamous and steamy on-air celebration, the couple inappropriately "celebrated" in front of a live audience.

Move over, Hef, because that’s the most playboy thing we’ve ever seen.



WWE's 15 Primetime Playboys

There’s rich, and then there’s "JBL rich."

Redefining wealth in the early 2000s, JBL showcased an astute business sense that paved the way to a fortune. Just like any true playboy, the Texas tycoon had no qualms showing off his riches, arriving to arenas in a white stretch limousine that barely fit on the ramp when it was parked.

Wearing fine tailor-made suits and appearing as a financial analyst on multiple television programs, JBL lived the lifestyle he preached and he constantly reminded others of how well off he was.    

JBL so exuded the playboy existence that when he left WWE in 2009, he took his giant cowboy hat and bank account and retired to a tropical island to spend his days in the lap of luxury.


Alberto Del Rio

WWE's 15 Primetime Playboys

All it takes is one glance at him, and you know that Alberto Del Rio thinks he’s better than you.

An aristocratic playboy of the highest order, Del Rio takes elitism to new heights, as his family lineage can be traced back to Spanish royals Ferdinand and Isabella. Arriving in arenas the world over in cars worth more than most folks make in a lifetime, Del Rio prefers the finer things — and he enjoys flaunting what he’s got.

Once inside the ring — after being introduced by his personal ring announcer, of course — Del Rio possesses great skill and has all the traits that make up a champion. So it was no surprise when, at SummerSlam 2011, Del Rio fulfilled his "destiny" by cashing in his Money in the Bank contract to become the first-ever Mexican-born WWE Champion.

Yet when push comes to shove, it’s Del Rio’s appreciation of high culture and his tangible disdain for anyone he views as being “lower” than him that fortifies his spot on our list of all-time WWE playboys.


"The Million Dollar Man" Ted DiBiase

The Million Dollar Championship debuts on The Brother Love Show

The Million Dollar Championship debuts on The Brother Love Show

Walking around with "The Million Dollar Man" as a moniker gives a guy an awful lot to live up to. In the case of WWE Hall of Famer Ted DiBiase, however, he managed to do just that.

Flying his own 747 to live events, DiBiase was so rich that he had a full-time manservant named Virgil in his employ. Seriously, who does that? An iconic scene that personified 1980s excess, DiBiase was regularly spotted peeling off hundred-dollar bills and sticking them in the mouths of felled opponents.

DiBiase was also famous for giving the WWE Universe glimpses into his extravagant private life. With Virgil in tow, DiBiase memorably visited a public pool to take a swim. When he arrived to find the pool packed with kids, however, The Million Dollar Man started throwing around the green and quickly made a public pool private.

He was such a player in fact, that he purchased his very own title.

The Million Dollar Championship was a solid gold, diamond-laced piece of bling-before-bling-was-cool that, though never officially recognized, served to solidify DiBiase’s place as one of the all-time great playboys in WWE history.

As he preached night after night to the WWE Universe, absolutely everybody had a price. You just needed to be rich enough to pay it. And DiBiase certainly fit that bill.


Ric Flair

Any respectable list of WWE playboys has to end with the "limousine-ridin’, jet-flyin’, kiss-stealin’, wheelin’-dealin’, son-of-a-gun" himself, Ric Flair! ( ALL-TIME PLAYBOYS PHOTOS)

Everything "The Man" did oozed the personification of playboy, from his fancy clothes to his late-night partying ways. Flair knew how to make an impression — he traveled in style, entered the arena in style and departed in style. Flying private jets to and from arenas all over the world and donning custom-made suits and robes that cost thousands of dollars, Flair certainly lived the life of "The Nature Boy."

All those fancy accoutrements served to add to his playboy persona. When it comes to the world of WWE, true playboys must have another key characteristic: They need to be able to win matches.

Say what you want about him, but Ric Flair knew how to win matches.

A 16-time World Heavyweight Champion, "The Dirtiest Player in the Game" was such a player that, at one point in his legendary career, his body was insured by Lloyd's of London, a move that was nothing short of pure, unadulterated playboyosity. And, yes, when you’re talking about Ric Flair, you’re allowed to make up words to describe his high-stylin’ ways.

As "Naitch" himself said, "To be The Man, you gotta beat The Man," and so far, no one has even come close to beating "The Man" at his playboy game.

WWE Shows Latest Results

View all Shows