Is there any more iconic figure in the notorious industry of sex appeal than the infamous Hugh Hefner? As the cornerstone of America’s controversial pop culture hit magazine Playboy, sometimes we might forget just how groundbreaking it truly was in this cross-section of women’s anatomy. At the heart of Playboy, and the driving force behind so much of the magazine’s success was the emphatic and perhaps “most interesting man in the world”, Hugh Hefner. Known for his business acumen and staunch knowledge for mass media, coupled with his incredible good looks was a match made in heaven (or hell, depending on how you look at it). As we flashback on some of Hugh Hefner’s most marvellous moments of glory, we’ll show you some absolutely stunning beauty, and nostalgic snapshots. These pictures may have been caught in the black and white era, but we think they are even more infamous for that exact reason.
During the mid and early 1950s, the country as a whole was attempting to further itself from decades of harrowing and brutal war across the globe. Playboy Magazine may have very well been the sigh of relief the country needed; allowing Americans to focus their attention on something far more interesting than newspaper headlines covering the world wars. They say timing is everything, and Hugh Hefner couldn’t have pinned the tail on the proverbial donkey with more accuracy if he tried. As we mosey down memory lane and glance at the beauty and entrepreneurial genius of Hugh Hefner, we encourage you to reflect on these pictures in stark contrast to how far similar images and magazines have come today. Playboy Magazine was truly a rocket propelled explosion into a previously unknown world of beauty and promiscuity.
19. With Carrie Leigh
No wonder so many males worldwide are jealous of Hugh Hefner, take a look at his calm and collected demeanor; even when seated next to the unbelievably stunning Carrie Leigh. The two lavishly gorgeous human beings were a couple once upon a time, 1985 to be exact, and images such as this one make us all a little weak in the knees. For the gentlemen in the audience Hugh Hefner resembles just about everything you could imagine and dream of as a man reaching the pinnacle of success in combination with beautiful women. Beautiful women such as Carrie Leigh as pictured here became routine for Hefner. He would come to create a persona unparalleled by any man in history for his courting beautiful women, and unfortunately with that comes heartbreak, as you probably already knew, these two hot lovers didn’t stand the test of time.
18. Raise A Glass!
With a look of pity for all of us, Hefner seems to be raising a glass to his life of success and the subsequent beauty that has engulfed his life. It almost seems like he has finally realized he’s made it in this picture, as if all the while before this one he was unsure. We’re not quite sure whether any of that is true, but honestly who cares? He is clearly enjoying himself, basking in the ambiance of his ambivalent nature, and carefree lifestyle. Flying by the seat of his pants (perhaps quite literally), Hefner embraces his untroubled days as they fall off the calendar, as if the days wake him, instead of the other way around.
17. New York Post
As an up and coming young entrepreneur, Hugh Hefner needed as much recognition as he could get. Newspapers such as the New York Post belonged in the upper echelon of agencies that could propel Hefner’s dream into super-stardom; and photographs like this one most definitely contributed to his overall success. Captured here with a plethora of women, the vivacious Hefner captivates us with an endless smile, thick wavy hair, and that signature cunning stare that was so commonly used as a weapon against all of us. As a young man trying to emerge himself in a relatively unknown market, he ultimately catapulted his business to the top almost overnight. The always smooth Hefner could almost always be caught in an advantageous pose such as this one, a style we would become all too familiar with.
16. Playboy Planes
In one of the few images we chose that has vibrant color, it allows you to grasp an even more spirited gaze into the past. With such an iconic protagonist as Hugh Hefner, we are half expecting a young Amelia Earhart to be alongside Hefner to balance the scales a bit. In the backdrop we are offered a sparkling view of the Playboy private jet, only fitting for such an honorary accord as this, and it leaves us wondering with such an extravagance offered in this picture, what must the inside of that jet look like? As captivating as the external gestures in this image, the real star of the show is Hugh Hefner (as always), with his effervescent stare and always dashing attire, Hugh Hefner truly embodies his title well.
15. A Glimpse At Beauty
As if for the first time in his life Hefner was caught off guard, he’s pictured here beaming into his own masterpiece. He appears to be simply glancing at the daily newspaper, but in fact it’s his own brainchild, filled with much more seizing subject matter. This image proves to us that no matter what he appears to be doing, reading, drinking, or working, he never appears to break as much as a bead of sweat. Undoubtedly mild mannered, Hefner grasps the magazine as if it was a rough draft, like he can pluck images and articles from the pages and make his revisions. Without a care in the world (it seems), he carries about his day with ease, like a locomotive gliding gently about its tracks.
14. Hugh Hefner’s Bunnies
Pictured here with his beautiful Playboy Bunnies, Hugh Hefner is truly center stage for this picture, but this may be one of the few images we’ve encountered where our eyes drift away from Hefner. As Hefner looks dapper as always, it’s hard to keep your eyes focused solely on him, as he is surrounded by jaw-dropping beauty (that just happens to be wearing skimpy bunny costumes). As always Hefner seems to almost be oblivious to his surroundings, smiling for the camera as if he has no awareness he has some of America’s most coveted and gorgeous women within arm’s distance of himself. We guess that with superstardom like Hefner is used to, this is just another day at the office for him, either way we sure are jealous!
It appears that all of these gorgeous women have a stunned look painted on their faces, while the always gathered Hefner revels at his advantageous daily tasks. With a rebel smile that can be seen from a great distance, Hefner’s warrior-like glare is enough to make us all a little weak. Like a mad scientist ready to reveal a sinister plot, Hefner stares through the camera and surfs amongst our thoughts. We can’t help but love the vigor and fore-with attitude he seems to always possess. Even with an image like this one, that can almost be plucked from a horror fiction novel, he seems to almost invite us into his mansion with a luring grin.
12. Too Smooth
With two beautiful women by his side, Hefner struts his way across the front patio of the Playboy Mansion. His hair blowing in the air, Hefner strolls with typical leisure as his arms wrap around two beautiful Playboy bunnies. With a fashion sense ahead of his time, Hugh Hefner led so much more than an enterprise with Playboy; he was a fashion star, a businessman, and a hell of a personality for his fans to revel in. If you look closely you can see Hefner gripping his long black pipe, something he was rarely caught without during his early period of success. As his success spread and his money grew, Hefner still kept his same calm and collected demeanor, always ready for the next business venture.
11. Living Color
Bursting with color, spice, and beautiful women, Hefner again rarely deviates from his swagger-filled persona. With a Playboy Bunny wrapped around each arm, and one laying in between his feet falling into his arms, he remains almost emotionless. Of course anyone as seasoned as Hugh Hefner as having beautiful women surrounding him, I guess the least we could expect is for him to look comfortable. If Hugh and Hefner are his first and last name, then “Smooth” is his middle name. It seems no matter what picture we find of him, he’s always ready to strike, which is good news for us. If you’re a female you probably want to do unspeakable things to get close to Mr. Hefner, if you’re a male you probably would do unspeakable things to be the coveted star.
10. Planes, Trains, And Automobiles…
Pictured here next to his private Playboy jet, Hugh Hefner is in a familiar position (you guessed it), alongside a cast and crew of babes and beauties. In an always dapper suit and tie, the Playboy entrepreneur casts a gaze that personifies his lifelong act in one snapshot, surrounded by his “employees”. It’s hard to imagine anyone playing Hugh Hefner’s role any better than the way he does. Pictured once more with his signature pipe, Hugh Hefner completely surrounds the pinnacle role of his time; his ability to “Wow” the women, while also remain ambivalent towards their affection. With his arm hooked around his “main” bunny, and his come-and-get-me smile that can be seen from a mile away, Hefner continues to knock us off our feet.
9. Origin Of Playboy
If we could all only be half as cool as Hugh Hefner during his prime, then we would all live in infamy. His endorsement on all things cool have left us all baffled over the years, and apparently the Playboy Bunnies caught on earlier than the rest of us. His incredible suits, even pictured in black and white images seem to pop out of the screen, his thick combed-over hair and translucent smile seem to be never ending. When first glancing at this photograph it’s hard to not notice all of the hair-dos, the old sixties grins, or the rest of the image that screams nostalgia, however the timeless Hugh Hefner seems like he could virtually fit in any era, old or new.
8. Barbie Benton
Seen here with his then girlfriend Barbi Benton, a multi-faceted talent known for her comedic skills, as well as obvious modelling prowess. These two love-birds dated for over a decade until their relationship took a drastic turn. Barbi Benton was looking for something more solidified with Hefner, and by all accounts Hefner regretted not marrying her, but ultimately Benton fell head over heals for tycoon George Gradow, who she would marry. Hefner’s top bunny for several years, was widely considered as the most beautiful woman of her era, and we can only assume Hefner had a few regrets with how the relationship ended, but we’re also guessing he didn’t have to wait very long to fill the void.
7. Airplane Lounge
Hugh Hefner doesn’t just rock the most average of scenery, he also knows how to party in style. We can only imagine that this room is the most modest of the things equipped behind the doors of the Playboy Private Jet. At first glance this lounge looks like it’s something that belongs inside the Playboy Mansion, much less their private jet. If this lounge traveling in the air at 30,000 feet is any indicator of what the plane has to offer, then we want to see more! Toasting to their excellence and extravagance high in the sky, we can only imagine that their dreams are floating as high as their private jet. Drinking on their exotic rug and undoubtedly headed toward an exotic destination, Hugh Hefner has struck again.
6. Office Bedroom
Is it possible for Hugh Hefner to look any more relaxed or in control than he already does? Apparently the style is second nature to Hefner as he appears to almost always be ready to have a picture snapped of him. The always elusive Hefner looks like a young Frank Sinatra mesmerizing us (and those bunnies) in his incredible Playboy Mansion. With the pipe dangling from the edge of his mouth like a tiny cigarette, and his half cracked come-and-get-me smile, he always seems to take the most historic photographs no matter how spur-of-the-moment they may be. With his lonely self (and four screaming hotties by his side), Hefner embodies the self-propelled image he set out to achieve.
5. A Smoke And A Pancake
The always devious Hugh Hefner gazes directly down the lens and into our souls, pictured alongside his precious bunnies this photograph captures an old keepsake of Hugh Hefner. Perhaps one of the oldest looking photographs we found, it trademarks our time capsule collection with a unique stamp on the cover. A pixelated snapshot from the past has a hard time relating to the future, however this image does grant us an opportunity to revel in the greatness of Hugh Hefner. No matter how old or new looking the photograph, or even Hefner himself, we can never truly rid our minds of how amazing he used to look (and how great he still looks).
4. The Look-Away
Does anyone rock the carefree look-away pose better than Hugh Hefner? This man has shocked us time and time again, and this image is no different. We can only assume he is gazing at an entry-way full of young, up and coming bunnies, because what else could be so mesmerizing? With a backdrop full of beautiful pictures filled with even more attractive women, a real-life playboy bunny around his hip, and most likely a mind chock full of attractive women, Hugh Hefner seems no more the wiser. We are truly envious of his ageless character and persona of a Greek god; sometimes we can’t help but stare at him instead of the women flocking him!
3. The Most Interesting Man On Earth
Caught mid-stride, it still seems as though Hugh Hefner is posing. Whether it’s marvellous camera work, or a god-like Hugh Hefner just nailing another photo opportunity, we as a collective audience couldn’t care less. Strolling with his usual entourage, Hugh Hefner seems right at home strolling with a flock of America’s most gorgeous women in his back pocket. As a self-made man Hugh Hefner seems to be even more modest than his demeanor suggests, his cool and collected personality seems to fit his role like a glove, his suits seem to fit his role even better. No matter what the scenario, we simply cannot get enough of Hugh Hefner being the absolute most interesting man on planet earth.
2. The White Devil
With the stunning white suit and the dazzling bunnies on either side, oh and the fact that the entire photograph is compacted with beautiful women, Hugh Hefner seems to not have a care in the world. Why should he? He has been successful his entire adult life, and with that success came one of the most extravagant lifestyles that popular culture has ever seen, he has lived a lavish life and continues to do so today. One thing is for sure, for long after Hugh Hefner has passed on, his legacy will go down in infamy. As one of the greatest personalities coupled with a product that has been widely considered one of the most popular magazines of all time, life is good for Hugh Hefner, and we sure are jealous!
1. A View From The Top
Try your hardest to focus on Hugh Hefner, okay who are we kidding. This bird’s eye view captures Hefner in a normality of his daily life, encompassed by gorgeous models and women alike. With an unusually enthusiastic grin painted on Hefner’s cheeks, he seems to be enjoying himself to the maximum, and we don’t blame him. This image portrays the persona of Hugh Hefner quite well, if you took the time to notice the other gentlemen in the photograph they appear to be enjoying themselves much less than the vivacious Hefner. This picture perfectly grasps just how much of a legend Hefner truly is, the timeless figure substantiates his trademark style with ease, still personifying his character to this day.