Marilyn Monroe

Marilyn Monroe never posed for Playboy, which is what made her appearance on the cover of the first ever issue in 1953 such a scandal. Inside the first issue were nudes of the actress taken four years prior, in an unrelated shoot. Hefner decided to use the pictures anyway without her consent. Oh, Hugh!

Lindsay Lohan

Things may have calmed down for Lindsay Lohan now but at one point, the poor woman could not catch a break (not helped by her taste for getting arrested). Around the time she was posing for Playboy, Lohan was still a bit of a question mark. She earned $1 million for her Playboy cover shoot.

Jaylene Cook

Mexico Playmate of the Year Jaylene Cook came under fire when she posed naked on a sacred Maori mountain in New Zealand. Cook’s intentions were to feel “freedom and empowerment” following a 12-hour hike to the top of Mount Taranaki. The photo, taken by her boyfriend, shows Cook in nothing but trainers, gloves and a hat. She later apologised.

Belen Rodriguez

It all came crashing down for Belen Rodriguez after she posted a video of her putting her tongue in her three-year-old son’s mouth. The Argentinian former Playboy model was slated for her actions, with some deeming it “inappropriate”. Rodriguez insisted it was an innocent act.

Jen Wilke

Posing in Playboy wasn’t enough for Jen Wilke, so she started a charity campaign asking the public to help her raise £7,500. Wilke claimed the money would help her attend the Maxim Hot 100 party. “It would mean the world to me to be able to focus on my modelling career exclusively,” she wrote. “I know that I am almost at a point where I could support myself and once I am there, I intend on using my profile and my position for the good of society. I just need to get there first.” She was criticised for the cash grab.

Elle Johnson

Elle Johnson made a big boob of it when she compared having her Instagram shut down with Doctor David Dao’s controversial removal from a United Airlines flight. Johnson, whose pictures violated community guidelines, wrote: “Booted off #Instagram again! They treat models like #United treated Dr. Dao. Not the physical abuse part-the random get off the plane part!”

Dani Mathers

Dani Mathers wasn’t just any Playmate. She was the 2015 Playmate of the Year. But she ended up under criminal investigation after taking a shot of a nude woman at her gym and posting it on Snapchat. “There is no excuse,” she later apologised. “I understand fully the magnitude of this post and that I have hurt a lot of people, women. Body shaming is not OK and is nothing to joke about. This was meant to be a part of a private conversation that never should have happened.”

Victoria Vetri

Victoria Vetri was Playboy’s 1968 Playmate of the Year but she would go on to become infamous for another reason. Vetri, who at the time used the name Angela Dorian, received a nine-year sentence for attempted voluntary manslaughter for shooting her husband during an argument in 2010.

Anna Nicole Smith

Anna Nicole Smith, like any celebrity going from rags to riches in the blink of an eye, was dismissed by many as an opportunist. When she was chosen as Playboy’s 1993 Playmate of the Year, she was already making headlines for her controversial marriage to billionaire J. Howard Marshall, who was 62 years her senior and died one year into the union. Smith herself died of an overdose in 2007, aged just 39.

Tanya Beyer

Tanya Beyer was gifted the title of Playmate of the Month in February 1992. In 2010, she was arrested in Florida for illegally buying and selling the painkiller Oxycodone from three separate doctors. After failing to show up to court, Beyer was declared a fugitive, later surrendering to police and held on a $100,000 bond.

Kim Kardashian

Kim Kardashian was everywhere in 2007. A notorious new member of Hollywood’s A-list thanks to both the leak/release of her sex tape and the debut of E!’s Keeping Up with the Kardashians, which would eventually see her become a multi-millionaire. Embracing her controversy, Kim posed for the December 2007 issue.

Colleen Shannon

Colleen Shannon, who was Playboy’s 50th anniversary centrefold, was arrested in 2012 after she smuggled her boyfriend Robert Skojo across the border and sentenced to four years in jail. She was forced to pay a $5,000 fine in addition.

Kristina Shannon and Karissa Shannon

Kristina and Karissa Shannon were the first twins to hit the big time in Playboy, appearing together in the magazine’s 2009 summer issue. They were later charged with felony aggravated assault after a fight that developed at a house party. The Shannon twins eventually received probation, and their careers took a nose dive in the aftermath.

Crystal Hefner

Crystal Hefner, as you might have guessed from the name, made headlines when she married Playboy founder Hugh Hefner in 2010. What people may not remember is that Crystal originally bailed on the relationship, breaking off the engagement just days prior to the marriage. They later reconciled and married in 2012. On her Playboy cover, ‘Runaway Bride’ was stamped over her body.

Dorothy Stratten

Dorothy Stratten was a Canadian Playmate who found success in the late 1970s. On the brink of forging a career in Hollywood, Stratten was tragically murdered at just 20 years old by her estranged husband and former manager Paul Snider in her LA apartment. Her life story would go on to inspire two movies: Death of a Centrefold: The Dorothy Stratten Story and Star 80.

Azealia Banks

Azealia Banks has never made life easy for herself in the limelight, and April 2015 wasn’t any different when she was picked to be on the cover of Playboy, much to the chagrin of her many haters. “Like, I hate white fat Americans,” she said in her interview. “All the people who are crunched into the middle of America, the real fat and meat of America, are these racist conservative white people who live on their farms”.

Sally Field

Yes, Sally Field! With all due respect to Ms Field, Playboy isn’t something you think of when you hear her name, what with all her serious acting credits on her CV. But back in 1986, she donned the famous Playboy costume for a cover shoot.

Gloria Steinem

Gloria Steinem, believe it or not, was something of a Playboy bunny back in the 1960s. While she never posed for the magazine, she worked as a cocktail waitress at New York City’s Playboy Club. Her experiences later contributed to her exposé A Bunny’s Tale, which caused considerable controversy for spilling the beans on a highly protected industry.

Jenny McCarthy

During her marriage to Jim Carrey, Jenny McCarthy established herself as a vocal anti-vaxxer, much to the annoyance of the liberal Hollywood circles she ran in. She started out posing for Playboy in 1993 and was an instant success with readers. She later divorced Carrey but stayed committed to equating certain illnesses with vaccinations, all of which are unfounded.

Elle Macpherson

Elle ‘The Body’ Macpherson was the source of much controversy for the 1994 movie Sirens, in which she appeared nude. After discovering that the media had been getting in touch with former boyfriends and offering money in exchange for explicit photographs, Macpherson agreed to pose nude for Playboy, working with the legendary Herb Ritts for the shoot.

Dolly Parton

Wholesome Dolly Parton turned down many lucrative offers to pose for Playboy during her heyday in the 1970s, before eventually agreeing to appear on the cover in October 1978 in the iconic bunny ears. It was seen as a big departure from her girl next door country image. Parton later recreated the look for her husband’s birthday.

Drew Barrymore

Drew Barrymore may well be through the other end of her personal troubles now, but they dogged her career all through the 80s and 90s. After struggling to adapt to the intense fame she received following her starring role in E.T: The Extra-Terrestrial in 1982, Barrymore was just shy of 20 when she posed for Playboy in 1995.

Marisa Papen

Marisa Papen is a little different from her Playboy model contemporaries in that she’s always been more conscious of the impact her opinions and photoshoots will have on conservative society. One of her more recent stunts saw her posing as a naked Virgin Mary while holding a black baby Jesus.

Jessica Alba

Jessica Alba didn’t want to be on the cover of Playboy, but she ended up there anyway. The magazine decided to cut an image from her poster for Into the Blue and run with it. This isn’t technically illegal, but it implied that there would be other images of Alba inside. Alba ended up filing a lawsuit against Playboy, claiming they had done “immeasurable harm” to her career.

Sherlyn Chopra

In 2012, Sherlyn Chopra posed for the cover of Playboy, causing a scandal in her native India, where the magazine was banned. Chopra was billed as the first Indian woman to appear nude in Playboy and on the cover of the magazine. It was a big move given that a lot of Bollywood films shy away from something as quaint as kissing.

Uma Thurman

A decade before the Alba controversy, Playboy bought pictures taken of a topless Uma Thurman at the beach in 1996 and ran them as a cover pictorial. Thurman has never been a prude when it comes to nudity in the name of consumerism, but there’s no doubting Hef and crew stepped over a line with that one.

Wall Street Women

Sometimes, Playboy would go out to find whole cultures of women who were open to getting their kit off and posing for the magazine. One such culture was the Women of Wall Street. Playboy convinced nine Wall Street women to model in the buff, only for most of them to eventually lose their jobs thanks to the shoot.

Girls of the Ivy League

Another group of women Playboy was interested in featuring in its pages were the bigwigs studying at America’s most prestigious colleges. In 1979, Playboy launched Girls of the Ivy League, convincing students of Yale, Harvard and Princeton to bare all. Safe to say, this did not go down well with the staff across these colleges.

Darine Stern

It took Playboy 18 years to feature an African-American woman as its cover model. The mag had featured two black models before: Jennifer Jackson in March 1965 and Jean Bell in October 1969. But Stern’s appearance stirred up some loyal readers who presumably weren’t comfortable with a non-white woman posing on their beloved publication.

Tiffany Fallon

When 2008’s Playmate of the Year Tiffany Fallon was bodypainted as Wonder Woman, comic book fans went nuts. Here was the inspirational heroine Wonder Woman, known for her corset and hot pants and created by S&M enthusiast William Moulton Brown, being sexualised for Playboy! Many critics found the move a step back for the feminist movement.

Sarah Kozer

Sarah Kozer, a Z-list reality show contestant, was slammed after she was chosen for the cover of June 2003’s Playboy issue, an honour that was usually bestowed upon the Playmate of the Year. This was important to readers, who saw the move as a sign of decay within the magazine. In their eyes, it should’ve been PMOY Christina Santiago up there.

Pamela Anderson

Pamela Anderson has graced the cover of Playboy on multiple occasions, and was known to be close with proprietor Hugh Hefner. An avid animal rights activist, Anderson has starred in multiple PETA ads. One such ad depicted the Baywatch star clad in a bikini with drawings on her body to designate ‘cuts’, such as “rump”, “thigh”, and, of course, “breast”. The ad, which was titled, ‘We All Have The Same Parts’, caused quite a stir and was banned in Quebec.

Marge Simpson

Technically not a real person, but definitely controversial. In 2009, Playboy honoured The Simpsons’ 20 year anniversary by putting Marge on the cover. The magazine also featured a spread displaying some seriously racy drawings. Unsurprisingly, not everyone was a fan of the sexualisation of a beloved cartoon character.

Bridget Marquardt

Model and TV personality Bridget Marquardt was a star of the reality show The Girls Next Door, which revolved around Hugh Hefner’s girlfriends and their lives at the Playboy Mansion. During an interview with Heather McDonald, Marquardt revealed that on her first night out with her costars she was pressured into having sex with Hefner.

Holly Madison

Another former resident of the Playboy Mansion who spoke out against Hugh Hefner, Holly Madison was never technically a Playmate, although she starred in The Girls Next Door. In a book titled Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny, Madison revealed that Hefner manipulated the girls to stoke conflict.

Patricia Margot McClain

Playboy’s November 1975 cover featured Patricia Margot McLain about to engage in a certain private activity whilst sitting in a cinema. The photo was a response to rival publication Penthouse, which was surging in popularity at the time. Unsurprisingly, the lewd image caused the more puritanical elements of American society to vigorously engage in their own favourite activity: getting offended.

Claire Sinclaire

Credit Ethan Miller via Getty Images

Claire Sinclair was crowned Playboy’s Playmate Of The Year in 2011. At the time, Sinclair was in a relationship with Hugh Heffner’s son, Marston. Their relationship was reportedly tumultuous, and in 2012 after the pair moved in together Marston ended up violently assaulting Sinclair, leaving her severely bruised and earning himself a ticket to jail.

Rita Jenrette

Posing nude for the April 1981 issue of Playboy, Rita Jenrette – the ex-wife of Democratic congressman John Jenrette – caused quite the stir for some comments she made when interviewed by the magazine. In an article titled ‘The Liberation Of A Congressional Wife’, Jenrette revealed that when they were still married she and John had “made love on the marble steps” of the US Capitol building.

Izabella St. James

After retiring from her life as a Playboy Bunny, Izabella St. James wrote a tell all book, Bunny Tales: Behind Closed Doors at the Playboy Mansion. In the book she claimed that the Bunnies were given an allowance of $1,000 a week, and that Hugh Heffner weaponised the payment, withholding it if the girls missed an official “going out night”. The Bunnies were also forbidden from having regular jobs, making them dependent on the allowance.

Stephanie Adams

Former Playboy model Stephanie Adams made headlines for the worst possible reasons in May, 2018. Adams had been fighting for child support since the end of her marriage, and was trying to move to Europe with her seven-year-old son, Vincent. After a judge sided with her ex and ruled that she couldn’t leave the country with Vincent, Adams leapt from her 7th floor hotel room, taking her son with her.

Cassandra Lynn

Cassandra Lynn was a model who, in February 2006, was featured as Playboy’s Playmate Of The Month. Lynn was known for her love of partying, and on January 15, 2014, she passed away from an apparent cocaine overdose. Her partner at the time, Gary Hensley, stepped in and has raised her two children ever since.

The Women Of Wall Street

In 2009, Playboy ran an advert seeking women who worked in finance to feature in a ‘Women Of Wall Street’ special issue. Hefner conceived of the idea after the 2008 financial crash, caused in large part by reckless Wall Street traders. Nine women answered the call and posed naked for the magazine. A few months after, Time Magazine followed up on them and found out most were no longer in employment.

Bettie Page

One of America’s most famous wartime pinup girls, Bettie Page saw her modelling career explode after featuring as the centrefold of a 1955 issue of Playboy. However, two years later the star disappeared from the spotlight. It later emerged that Page struggled with severe schizophrenia, and at one point was arrested for assaulting her landlady.

Kimberley Conrad

Kimberley Conrad was one of Playboy’s most iconic Playmates, earning the Playmate Of The Year title in 1989. She also ended up marrying Hugh Hefner, but the marital bliss didn’t last. A feud over money quickly erupted after the pair’s separation, and in 2009 Hefner sought to officially divorce Conrad, claiming he had given her over $12 million in support payments.

Jayne Mansfield

Jayne Mansfield was an American actress, model, and lusted-after sex symbol. Mansfield appeared nude in four separate issues of Playboy. Whilst she might have been a happy Bunny, her husband, Paul, decidedly wasn’t. In 1956, Paul filed for sole custody of the couple’s child, citing the fact that Mansfield’s decision to pose nude for Playboy made her “unfit to be a mother”.

Shanna Moakler

Shanna Moakler has graced the pages of the Playboy numerous times, and was crowned Playmate of The Month in December 2001. Moakler married Blink-182 Travis Barker drummer in 2004, but their relationship eventually fell apart amid rumours that Barker was cheating with Paris Hilton. In 2006, tensions boiled over in an LA nightclub, and Moakler allegedly caught Hilton in the jaw with a haymaker.

Kendra Wilkinson

Another star of The Girls Next Door, Kendra Wilkinson also appeared in three issues of Playboy. Wilkinson’s career as a model was launched by her time with Hugh Hefner, which began when she was 18, but she later turned on the publishing magnate, claiming that he was controlling and manipulative.

Karen McDougal

Playboy’s 1998 Playmate Of The Year, Karen McDougal, got embroiled in some controversy involving none other than Donald J. Trump. According to McDougal, the pair had an affair whilst Trump was married, and in 2016 McDougal sued to be released from a legal agreement forbidding her from speaking publicly about the event.

India Allen

Another lawsuit involving a Playmate, but this time it was the Bunny on the receiving end. In 2012, a skincare company claimed in court that it had paid India Allen – Playboy’s 1988 Playmate Of The Year – $25,000 to create a makeover-based reality TV show which never materialised.

Reneé Tenison

Darine Stern might have been the first Black woman to feature on the cover of Playboy, but Reneé Tenison was the first to win the coveted Playmate Of The Year title. Tenison later recalled during an interview how the locals in the small Idaho town she grew up in were shocked when they discovered she had stripped down for the magazine.

Carmella DeCesare

Carmella DeCesare – 2004’s Playmate Of The Year – found herself in legal hot water when she got into a bar fight with a woman named Kristen Hine. It emerged during trial that Hine had been involved in an affair with DeCesare’s boyfriend. The assault charge was eventually dropped, but the model was found guilty of violating a restraining order and sentenced to community service.