The passing of Hugh Hefner marks the end of an era. One of whimsical parties, days by the pool, nights out on the town and a seemingly endless array of lovely young ladies traipsing about with the ultimate playboy, hoping for a chance to appear on the glossy pages of Playboy magazine.

Hef has taken flack over the years for many of his lifestyle choices. His decision to spend his time with a long list of different women, his many eccentricities and even his wardrobe consisting mostly of stylish robes has been the talk of more than one juicy tell-all book which have been penned by his past flames. One of his former girlfriends, Holly Madison, painted quite a picture of what life was like inside of the Playboy mansion in her memoir Down The Rabbit Hole. The many buxom, blonde beauties who have spent time as Hefner's girlfriends, most of whom were young enough to be his granddaughters at the time, may have truly loved him, or they may have been hoping for a chance at being named Playmate of the Year.

Whether a woman regrets her choice to pose for Hef’s iconic girly magazine, or is proud of the fact that she was once a Playboy Bunny, no one can deny the fact that stripping down for a steamy Playboy photoshoot is usually a sure-fire way to help one’s aspirations for fame and fortune become a reality.

The following 20 moms have posed for Playboy, and will forever be a part of a legacy left by the man behind the scandalously pretty pictures: Hugh Hefner himself. He may be gone, but the sultry shots he helped create will live on forever. Read on to discover which 20 celeb moms have taken a turn posing for the Playboy.

20 Madonna

Nude photos of Madonna appeared in the September 1985 issue of Playboy. The Material Girl posed on the cover in a lace top, a short skirt, a thick black belt and an oversized green blazer. Her facial expression epitomized the ultimate bad girl, and the headline read, “Madonna Nude: Unlike a Virgin...For The Very First Time.”

Madge is the proud mama of six children, some adopted and some biological. She’s not your typical mother, and has been accused of setting a bad example for her growing tots with her partying ways. The chart-topping singer is unapologetic about who she is, and has shared, “I'm tough, I'm ambitious, and I know exactly what I want. If that makes me a b****, okay.” She has also wisely stated, “No matter who you are, no matter what you did, no matter where you've come from, you can always change, become a better version of yourself.”

19 Charlize Theron

Oscar-winning actress, Charlize Theron has two beautiful adopted children: a daughter, August, and a son, Jackson. Before she became a mother, Theron appeared in Playboy-- a move that was most assuredly celebrated by her fans around the world. She posed nude for the May 1999 issue. The star appeared on the cover in a steamy shot that featured her from the chest up wearing nothing but her birthday suit. She tastefully covered her assets with her hands in the cover pic, but the shot left little to the imagination.

Theron is an advocate for women’s rights, and has boldly stated, “I think today women are very scared to celebrate themselves, because then they just get labeled.” She has also admitted to being a girly girl. She is unashamed of her love of fashion, and has joked, “If they ever do my life story, whoever plays me needs lots of hair color and high heels.”

18 Kate Moss

Supermodel Kate Moss got the honor of posing for the cover of Playboy’s 60th anniversary issue. The January/February 2014 issue featured Moss posing on her knees in classic Playboy bunny attire including a black satin bustier with bunny ears to match along with a black and a black and white bow tie.

Moss has one daughter, Lila Grace, with her ex Jefferson Hack. The mother-of-one is humble about her gorgeous looks, and once shared, “You can be a pretty face, but if you're not a nice person, it just doesn't work. I'm not traditionally a beauty, but apparently people think I'm all right. If you're a nice person, it definitely helps.” Moss was undoubtedly chosen for the 2014 cover due to the fact that she is considered one of the greatest models of all time. Unfortunately, she’s also taken heat for statements she’s made about her extremely thin frame, and once quipped, “Nothing tastes as good as skinny feels.”

17 Geri Halliwell

Former Spice Girl Geri Halliwell appeared on the May 1998 cover of Playboy sporting a tight-fitting tank featuring the British flag along with barely-there black bottoms. She posed with one hand pointing upwards disco style, and the other hand clutching a microphone and planted firmly on her hip. The cover featured the headline, “Spice It Up,” which Halliwell certainly did. The singer is now the proud mother of two children: a daughter named Bluebell, and a son named Montague.

Halliwell has opened up about how much she adores being a mother, and has also admitted she is learning as she goes. She has shared, “My daughter is the biggest gift; I've said it so many times and it sounds like a cliche, but the thing about being a parent is when you think you've cracked it, and you're on top of your game, they change again and you have to catch up and adjust. I feel such a responsibility to instill good values in her, to be polite, to have discipline.”

16 Elle Macpherson

Supermodel Elle Macpherson has been nicknamed “the body,” and it may have been her appearance in Playboy that helped her clinch this coveted, yet controversial, title. Macpherson is the mother of two boys: Arpad and Aurelius. It may be best if they never see the May 1994 cover of the mag, which features Macpherson in nothing but black, see-through stockings. She is hugging her nude upper half in the shot, and her face can only be described as fantastically fierce.

She may have the advantage of being one of the most beautiful women in the world, but Macpherson still has insecurities. She has admitted to working hard to overcome them and love herself as she is. She has shared, “It's not vanity to feel you have a right to be beautiful. Women are taught to feel we're not good enough, that we must live up to someone else's standards. But my aim is to cherish myself as I am.”

15 Farrah Fawcett

Charlie’s Angels star Farrah Fawcett has become known as the ultimate pin-up girl, and her appearance in Playboy most likely had something to do with it. She appeared in the July 1997 issue, and was also featured on the cover. One of the cover’s headlines read, “Farrah’s Naked Art Special,” and the actress is pictured on her hands and knees on a bed with mussed-up hair, a black negligee, and black stockings. Her facial expression is nothing short of a killer come-hither stare.

The late Fawcett had one son: Redmond O’Neal with Ryan O’Neal. She was a loving mother, but also had a sensual side that couldn’t be ignored. She once joked, “God gave women intuition and femininity. Used properly, the combination easily jumbles the brain of any man I've ever met.” Fawcett also wasn’t afraid to admit that she knew she was hot stuff, and even admitted, “I am proud of what I have got and I need an audience.”

14 Sharon Stone

Mother-of-three Sharon Stone appeared on the cover of the July 1990 issue of Playboy next to the headline, “Sharon Stone: She’s Got Hollywood Breathing Heavy.” The cover shot featured a close-up of Stone wearing nothing but a bracelet, and holding some sort of gem up to her pouting mouth. Her cleavage is ample in the pic, and her curly hair is tousled to perfection, proving that sometimes, less is everything.

Stone is one actress who has always been unapologetically herself, and she has embraced her femininity during every stage of her life. She has shared, “I've never been willing to lie about my age. Why on earth would I want to tell people I'm 35, which I'm not, and have them say, 'Oh that's nice,' when I could tell them I'm 47, which I am, and have them look at me and go, 'Whoa!'. I'm not afraid of aging. I stopped being afraid of life a long time ago.”

13 Kim Basinger

Former Bond girl Kim Basinger turned more than a few heads when she graced the cover of Playboy in February of 1983. The actress, who has one daughter, Ireland, with ex Alec Baldwin, is pictured on the cover lying on her stomach clutching a pocket watch, her blonde curls cascading down around her face. The pic is one of the least scandalous Playboy has released, with nothing more than a bare shoulder being shown. It is, nonetheless, a super steamy shot.

Basinger’s tumultuous relationship with Baldwin has been a source of pain and embarrassment over the years. Additionally, the actress has found it difficult to overcome stereotypes placed upon her as a young actress. She has admitted, “I think any girl who comes to Hollywood with sex symbol or bombshell hanging over her has a rough road.” As Basinger has aged, she has learned more about herself, and what works best for her. She has also stated, “I feel there are two people inside me--me and my intuition. If I go against her, she'll screw me every time, and if I follow her, we get along quite nicely.”

12 Drew Barrymore

Mother-of-two Drew Barrymore has admitted to having a bit of a checkered past. The child actress appeared in the January 1995 issue of Playboy when she was just 19 years old. She posed on the cover in a tight-fitting white t-shirt that featured a black Playboy bunny. The headline read, “Drew Barrymore In The Flesh.”

Drew has since cleaned up her act, and has left her wild child days behind her. She has admitted, “I am not someone who is ashamed of my past. I'm actually really proud. I know I made a lot of mistakes, but they, in turn, were my life lessons.” Barrymore’s main focus now is being the best mother she can be to her adorable daughters and taking on projects she feels passionate about. She has shared, “I think happiness is a choice. If you feel yourself being happy and can settle into the life choices you make, then it's great. It's really, really great. I swear to God, happiness is the best makeup.”

11 Brooke Burke-Charvet

Fitness guru and television host Brooke Burke-Charvet appeared nude in the December 2004 issue of Playboy. She also posed on the cover in nothing but a red satin sheet and red hoop earrings next to the headline “Brooke Burke Nude: Wild Off E!” Not your typical holiday card photo. Burke-Charvet is now the proud mother of four darling babies, and, we must say, her rockin’ bod may be better than it’s ever been.

On being a mom, Brooke has shared, “I think with motherhood and child-rearing in general, everyone's going to tell you how to do it and why. I've always said to other mothers and women when they've asked me, that you have to find your own way and find out what works for your family, at all costs.” She has also stated, “Going into a pregnancy is a really challenging time for a woman, because it's forever-changing, both mentally and physically.”

10 Anna Nicole Smith

The late Anna Nicole Smith was a Playboy favorite before her tragic death in 2007. She was named Playmate of the Year in 1993, and appeared on the cover of the mag in 2001 wearing nothing but pink elbow-length gloves and gobs of diamonds. The headline read, “Anna Nicole Smith: $450,000,000 Playmate.”

Anna had two children: Daniel, who mysteriously passed away shortly before she did, and Dannielynn, who was only 5 months old when her mother died of a drug overdose at the age of 39. Anna Nicole was a broke single mother when she decided to attempt to make a living off of her looks after other avenues didn’t pan out. She once shared, “I couldn't make ends meet. I tried Red Lobster. I tried Wal-Mart. I tried all these places and I couldn't make it. I couldn't. So, I tried this gentlemen's club, and, you know, I worked there, and it was just awful in those places. It was terrible.”

9 Tiffany

Pop star Tiffany decided to pose for Playboy in the hopes that she would be seen “as a woman” instead of the teen singer she was when she became a household name. She graced the pages of the mag’s April 2002 issue. She also snagged the cover shot in which she is seen smiling in a white semi-see-through leotard complete with cut-outs made to accentuate her cleavage. One of the issue's headlines reads, “Teen Queen Tiffany All Grown Up: Totally Nude.”

Tiffany is now the proud mother of one adorable son, Elijah,whom she shares with her ex-husband, Bulmaro Garcia. She has been married to her current hubby, Benn George since 2004. It is unclear whether or not her choice to pose in her birthday suit helped her to feel like more of a woman, or if she is now singing a different tune. The “I Think We’re Alone Now” singer once stated, “Everything will be good as long as you do your best. Because if you do, there will be no regrets.”

8 Denise Richards

Actress Denise Richards helped make the holidays merry and bright when she appeared in the December 2004 issue of Playboy. Charlie Sheen’s ex was stunning on the cover of the mag in a close-up featuring big hair, tree-ornament baubles in her ears and a million dollar smile. The headline next to Richards’s killer close-up read, “Denise Richards: Drop Dead Gorgeous, 10 Pages of Erotic Nudes.”

Denise has three beautiful children: Lola, Eloise and Sam. She is a pro when it comes to posing for the camera, and loves every opportunity she is offered to get glammed up. She once admitted, “Every photo shoot, I'm always asking the makeup artist what they're using on me, and I'll go out and get it.” Her relationship with Sheen may have been a mistake, but Denise shines when she gets in front of the camera. In her opinion, if she’s at peace with her decision to pose nude, the rest of the world should be too.

7 Kelly Kiloren Bensimone

Author, socialite, reality television star and mother-of-two Kelly Kiloren Bensimon made the controversial decision to pose nude for the March 2010 issue of Playboy. She appeared on the cover in nothing but a red sheet strategically wrapped around her body next to the headline, “Bravo TV’s The Real Housewives of New York City Kelly Bensimon: Unwrapped.”

Bensimon has been a controversial character over the years, and has been a part of her share of friendly feuds, but her smile is contagious and her congenial attitude is admirable. It’s not surprising that she was selected to appear in Playboy. She’s one hot mama, after all. Posing in nothing but what a person was born with isn’t for everyone, but many believe those who are brave and bold enough to go through with doing so deserve nothing but praise. In the opinion of many, her daughters should be proud of their mother’s confidence.

6 Heidi Montag

Heidi Montag is currently expecting her first child with her infamous hubby, Spencer Pratt. The controversial reality TV star posed for Playboy in 2009. She graced the cover of the mag dressed in a white barely-there bikini. The Hills alum was covered in mud, in a sexy way, and a bunny was drawn into the dirt smeared on her tummy. The headline read, "The Hills Are Alive! Heidi Montag: The Gossip, The Drama, The Dirt."

Heidi has been heavily criticized by fans for her choice to undergo multiple plastic surgeries that have rendered her nearly unrecognizable from her former self. The mom-to-be has admitted, "I definitely regret the surgeries that I have had over the years, I think I was so young and in such an unstable situation in my life with so much going on and so much pressure." She has also confessed, "I got too caught up in Hollywood, being so into myself and my image."

5 Jaime Pressly

Before Jaime Pressly became a mother, she posed nude for Playboy. The My Name Is Earl star heated up the cover of the February 2004 issue in a bright white, soaking wet cotton dress. The teeny-tiny spaghetti strap number clung to her in all the right places, and the image has been dubbed by some one of the sexiest Playboy covers of all time.

The stunner has one son with her partner Eric Cubiche: Dezi James Calvo, and the happy couple is preparing to welcome twins to the world in the very near future. Despite her time spent in the spotlight, Pressly claims she isn’t the typical famous person. She has stated, ”I don't want to be the Hollywood girl... I'm Southern and old-fashioned.” Jaime owns the choices she has made in her life. She has also shared, “Everything I did and continue to do happens for a reason, and honestly, I don't regret much in my life.”

4 Tamara Ecclestone

British model, socialite and television personality, Tamara Ecclestone may have been born with a silver spoon her mouth, but she’s definitely made a name for herself all on her own as well. Her sparkling, radiant personality is almost as blingy as her Playboy cover. The mother-of-one graced Playboy’s May 2013 issue alongside the headline, “The Diamond Heiress.” In the cover shot, Ecclestone is nude save for a diamond which she is holding over her nether regions and some tastefully placed sparkles concealing the most private areas of her chest.

Ecclestone has admitted to wanting people to know she’s just like everyone else, even though she’s living her life in the public eye. She has shared, “I want people to see that I'm a real person, I overreact, I cry, I'm emotional. If I come across as perfect and in control, that wouldn't be who I really am.” She isn’t afraid to celebrate every part of herself, and has also stated, “As a woman, I believe you have to embrace your body, and feel beautiful both inside and out.”

3 Garcelle Beauvais

Garcelle Beauvais is proud mother of three beautiful boys: Jax, Jaid and Oliver. She stripped down for the August 2007 issue of Playboy, and graced the cover clad in a lavender mesh number that left nearly nothing to the imagination.

Beauvais has been open about the fact that she played a part in her very public divorce from Mike Nilon, who she caught being unfaithful. She has shared, "Divorce isn't one-sided, and I am by no means perfect. Becoming accountable for my role in the relationship was very empowering." Speaking on the subject of parenting, Beauvais has stated, "Conversations between parents and kids are important - about race issues, about all kinds of things, about heritage." If her boys ever get ahold of the steamy shots of their mama, the ensuing conversation is most likely going to be slightly awkward.

2 Kim Kardashian

Just two months after the soon-to-be hit Keeping Up With the Kardashians aired on E!, Kim Kardashian-West bared all for the December 2007 issue of Playboy. She also appeared on the cover in a skimpy red piece of lingerie. Kardashian-West has since catapulted into the spotlight. She has two children with her husband, Kanye West, and just confirmed that the couple is expecting a third child via surrogate. It may be partially thanks to Playboy that Kim is the major celebrity she is today. After the news broke of Hefner's death, Kim tweeted, "Paris and I are reminiscing about the Playboy parties at the mansion and how much we love Hef. She’s texts me the perfect Hef emojis."

Kim has dealt with her share of haters, but she tries not to let it get her down. She once admitted, "If I don't feel confident about my body, I'm not going to sit at home and feel sorry for myself and not do something about it. It's all about taking action and not being lazy. So you do the work, whether it's fitness or whatever. It's about getting up, motivating yourself and just doing it."

1 Joan Collins

British author and actress Joan Collins has been married five times, and has three beautiful children to show for her many unions. Collins posed for the December 1983 issue of Playboy, and graced the cover of the issue in a festive sequined red dress with a plunging neckline that was accessorized with crimson elbow-length gloves. The look was completed with an updo for the ages.

The timeless beauty once shared that she wishes she would have enjoyed her youth and embraced her looks while she was in her prime. She has admitted, "I never thought I was particularly good looking. But when I see old photographs, I realize that I was. I do wish I had known that at the time because beauty is power. I didn't realize how lucky I was to be young, beautiful and in Hollywood. It didn't hit me. Every day I woke up, went to the film studio and just got on with it."

Sources: EOnline.com, NewYorkDailyNews.com, People.com