Playboy's 10 Biggest Mistakes That Ruined Their Identity

Created by Hugh Hefner in 1953, Playboy has become an iconic magazine where he tapped into the male audience seeking pictures of beautiful women. Yes, there were “in-depth” articles, too. But who was paying attention, really? They were white noise next to photo spreads of naked women.

Fast-forward to the 21st century, Playboy is still widely popular as a brand, despite  competition from everyone and everywhere. They have been able to capitalize on trends and pseudo celebrities at the right time. They also have found the newest diamonds in the rough for us to go cover and enjoy their beauty.

Playboy is not perfect. They’ve hit major roadblocks in recent years. Some of these obstacles were overcomed, like the Lindsay Lohan debacle. Others? Not so much. Case in point is Playboy’s recent announcement their iconic magazine will no longer feature nude women. This is problematic as the Playboy brand was built on the very desire – of every man in the world – to see desirable women naked.

As Playboy faces an apparent identity crisis in an age where accessing images of naked women is rather easy, and free, too, we take a look at some of the biggest mistakes the empire has made during its existence which has ruined the brand’s identity.

10. The Lindsay Lohan Disaster

Jimmy Jellinek, president of entertainment at Playboy Enterprises, proclaimed that he “still has an ulcer” over his “soul-sucking” journey that was the Lindsay Lohan Playboy shoot. Jellinek speaks of dealing with managers, lawyers, agents and handlers that drove him insane. This only added to the circus of paparazzi hanging from trees, driving in decoy cars and even helicopters flying around for sneak peeks. Then there was the actual shoot which had to be fit in between Lohan’s court dates and had to be completed prior to her sentencing. Jellinek stated: “Anytime you’re dealing with a train wreck, you yourself have to get on the train.” The experience was exhausting for Jellinek and never lived up to the hype. Jellinek jokes that not only did the shoot “age” him but it got him “into therapy, so that was good.” The Lohan shoot turned out to be much more hype than substance and quickly faded away.

9. Photoshop Debacle

There is an art and a science to putting together a successful magazine. It doesn’t matter if it is Playboy or GQ, the magazine is carefully constructed by many experts. These talented individuals are responsible for putting the finishing touches on the photos that make or break magazine sales. Many times, it’s the photos themselves that drive sales of the magazines; especially inside Playboy’s hallowed walls. So when a graphic artist makes a mistake touching up a photo, it can be pretty major. We aren’t talking about any small mistake either. We are talking about a big error, as in, making someone’s belly button disappear. What’s worse is that everyone else who looked the magazine over prior to release also missed the error. One word: embarrassing. The Latin beauty was wearing a sexy, tight soccer top that displayed her entire mid-drift and tiny shorts that revealed all smooth belly that had miraculously covered her belly button. Eesh.

8. Caitlyn Jenner In Playboy

When you are a magazine catering predominately to heterosexual men, placing a newly-anointed transgender 65-year-old woman on the cover is not the way to go. Let’s begin with the obvious: this is all hype for the magazine to draw attention to itself. But at a hefty $5 million price tag, it is borderline insanity. Secondly, what men are going to clamor to this release? It makes no sense. This is all happening as Playboy’s image and sales are precipitously dropping. Jenner’s response: “I’m really excited to show off my new parts and I want people to realize that you don’t have to be ashamed of yourself and to also embrace sexuality.”

This disaster is neither appealing nor does it make any sense. I find myself shaking my head at this just as much as ESPN honoring Jenner at the ESPY’s. Hey, to each their own. But really, let’s all not board the celebrity crazy train and latch on to hype above substance. Let us not forget that Jenner is the focus of a nasty traffic accident that left someone dead. The case likely is going to Civil Court and not criminal, but let’s at least hear all those facts before applauding this individual.

7. Playboy Announces Wine Sales

We are attempting to ascertain exactly what this means. The headline says it all and also is a major head scratcher. In 2012, Playboy entered the wine business. They inexplicably started an online wine club. At its core, the headline doesn’t compute or make much sense. Clearly, Playboy is searching far and wide to expand their brand into other avenues before they go completely belly-up.

“The Playboy lifestyle is about bringing the best the world has to offer to consumers,” Scott Flanders, CEO of Playboy Enterpris, explained. If this strange turn wasn’t enough, Playboy got sued for over $12 million for Enron Style reporting over the wine sales. The lawsuit claims that it failed to pay millions of dollars in commission fees. Who knows where this is heading, but Playboy is desperately trying to create other revenue streams. Getting sued probably isn’t going to be the way to do it.

6. Liz Dickson Sues Playboy

Beautiful model Liz Dickson was asked to lie on her stomach at a Playboy event. The model was scantily dressed and a golf ball was placed between the top of her butts cheeks. Now, many people would be like, “what is she, an idiot?” But let’s be honest, she is a terribly paid model who wanted to break into a very difficult business. So being a show pony at this event sort of goes with the territory. But the golf ball and subsequent swing was both embarrassing and costly for Playboy. The ball was struck, but so was Dickson’s rear end. It was comedian/actor Kevin Kline who took the fateful swing. Dickson’s rear end was sore and she was embarrassed. What started off as an embarrassing smile and a small welt ended up in court with a massive bruise. The model was clearly abused at this event, all caught on camera mind you. Naturally, her lawyer claimed she had tingling in her leg and some numbness. Playboy paid up.

5. Old Brand

If something isn’t broken, you don’t fix it. We get the old adage, but Playboy has been so successful for so long it’s as if they never saw the Internet coming. And when the World Wide Web came along, it blew up Playboy’s business model like a bad Sly Stallone movie. See, Playboy specialized in beautiful naked women tastefully photographed in their magazines for decades. But when the Internet came along and oversaturated that model, allowing websites and individuals to post as many naked photos as they wanted, Playboy was slowly but surely etched out dollar by dollar. Even Playboy’s movies and the channel got pushed to the side with sexy quality films being produced by nearly everyone and anyone with no price tag attached. Who wants to pay a hefty price for Playboy when the content is free? Not many. And so Playboy’s model got pushed aside and their business is quickly failing. Playboy is currently seeking as many E-business avenues as it can muster (like the Playboy Wine Club for example).

4. Cheap Cover Tricks

Playboy magazine has had some epic covers over the years. But the company went from providing substance and quality to going for gimmicks and over-hyped celebrities. The end result was putting celebrities on the cover who had no business being there. It is absurd to put the likes of La Toya Jackson on the cover and show spreads of unattractive women just for hype sake. Equally of importance is putting beautiful celebrities like Jessica Alba on the cover only to lure people into thinking that she “may” be posing naked inside. While Jessica poses in a bikini, male onlookers sport the “WTF” face. The fact of the matter is, Playboy has been going for cover tricks and lowbrow notoriety instead of discovering the next most beautiful model/woman around. Playboy used to be a phenomenal feeder system for stardom. Now it is doing its best impression of the Titanic.

3. Marge Simpson Dawns Cover

It’s one thing to do cheap gimmicks with unattractive women or to toss in clothed celebrities just to get some extra hype. But when you add Marge Simpson on the cover of your magazine, you have clearly jumped the shark. Playboy shows its desperation in trying to place a cartoon character on the front of the magazine in hopes of being the lead story on the evening news. It’s embarrassing that this fabled and storied magazine would sink to such idiotic depths as to put a middle-aged unattractive cartoon character on the cover. What about some of the hot Japanese anime characters? Are we going to start putting naked cartoon characters in the magazine in lieu of putting the effort in to create a high quality magazine? Who knows. But one thing is for certain, Playboy is in big trouble. And we will add a “Doh!” to this one.

2. Playboy Mansion For Sale?

This is crazy! It would be like the United States of America selling the White House to pay off some of our debt. When rumors began to surface that Playboy was in such bad shape that Hugh Hefner was considering selling the Playboy Mansion, shock-waves were felt through the world. The reality is, the Playboy Mansion exists in name only because it is the epicenter of all things that Playboy represents. We are talking about scantily-dressed women roaming around and lots of partying and sex; and of course, Hef himself.

That is, at its core, the ideals behind Playboy and what it is selling. But once the mansion goes, so goes the empire. The Playboy Mansion is like the Death Star and without it, the brand will die (see the second trilogy of Star Wars for this reference). We know Hef was forced to sell the property nearby for far less than its list price. We can only pray that the Mansion isn’t next up on the auction block.

1. No More Nudity

“Whatchu talkin’ about Willis?” Did someone actually say this? Is this going to be a thing? Is it true that the magazine will no longer feature naked women? WTF! I mean, so we’re just going to have sexy women in just their underwear? I believe we call that the Victoria’s Secret catalog. I don’t get this. So we’re adding clothing to hot attractive women now and calling it Playboy? While others are pushing less and less clothing, Playboy apparently believes that its articles will sell its magazines? Unlikely.

Men are visual and reading about sunsets on the beach and favorite colors just isn’t going to do it. Sorry, Playboy, but this is an epic fail and further displays the weakness of your brand. We understand that the model is broken, but doing a complete overhaul on who and what you are isn’t going to sell magazines. Maybe that’s the point. The days of holding a new Playboy in your hand appear numbered. This latest effort is case in point.