Twelve days, twelve Playmates, and twelve snapshots of the moments that make them unforgettable. Drawn from the Playboy archives, this pictorial revisits the Playmates of the Year across decades, each captured at a point where confidence, curiosity, and timing all aligned. From pearls and pinup glamor to motorcycles, mistletoe, and moments we will never forget, these women reflect many ways that beauty, ambition, and individuality have shaped the Playboy legacy. 

One Playmate draped in pearls

Upon being crowned the 1987 Playmate of the Year, southern belle Donna Edmonson shared “I didn’t think I was pretty enough to even test for Playboy, let alone be Playmate of the Month. Now I am Playmate of the Year! This has really been a dream come true.” She was content to end her modelling career after her time with Playboy, likening the experience to that of a fairy tale, allowing her to be “Up in the sky, looking down on myself. And I’m flying!”

A second Playmate in princess curls

Once upon a time, Kara Monaco claimed the title of the first-ever “Miss June” to be selected as Playmate of the Year in 2007. Between her sparkling emerald eyes, high heels, and love of spontaneous moments, she naturally drew fans into everything she did – and she loved responding to her spellbound fans, enjoying every adoring moment.

The third Playmate lost in bubbles

“For once, I didn’t have to be anyone except myself.” Eugena Washington sought to share a different side of herself as the 2016 Playmate of the Year, delivering a pictorial that spoke to sex, charm, and truth. A Playboy photographer knew she would shine as a Playmate, and her trust in his judgement allowed him to capture her unmistakable presence with ease. 

Our fourth Playmate posing pinup trouble

Clair Sinclair’s love of pinup icons Dita and Bettie, paired with her vintage taste, fueled her passion for burlesque and her swift rise to being chosen as the 2011 Playmate of the Year. Her Playboy photos were a tribute to glamour of the pinup error, with her fearless recreations including swinging 10 feet in the air. According to her, this was a “dream come true.” 

The fifth Playmate waiting under the mistletoe

Sharon Clarke’s fresh face captivated Playboy editors while she was teaching English to local high school students in the Truk Islands, leading to her unanimous selection as 1971’s Playmate of the Year. She shared her passions for travel, environmental advocacy, and love of non-contemporary literature with Playboy readers – paired with pictorials that captured hearts in an instant. 

A sixth Playmate is the sweet girl-next-door, irresistible

With her feet firmly planted in Cleveland, Carmella embodied the girl next door in her 2004 Playmate of the Year feature. Playboy editors described her as more comfortable in a baseball cap than a tiara – though you’d never know it from her sizzling presence in front of the camera. For her, the Playmate experience meant “there [was] never a dull moment, and honestly, it [was] awesome”

Our seventh Playmate is wrapped in soft sheets about to slip

Natural beauty Christina Santiago shared that she was firmly against anything phony – she didn’t like cheesy lines, and she was clear that “Real breasts feel better… Plus, more than a mouthful is just too much.” Despite the opportunities to rub up against the famous life as the 2003 Playmate of the Year, Christina described herself as a chill girl that preferred to go to a dive bar to drink beer with her friends. Her Playmate profile closed out with her promise – “if I ever see myself turning into something else, I will get on an airplane and go back home.”

An eighth Playmate riding low on a motorcycle trip

You wouldn’t know that 2012 Playmate of the Year Jaclyn Swedberg once battled “brutal shyness” before her Playboy casting call. The once shy girl became a daredevil extraordinaire, rappelling down Argentinian mountains and regularly appearing on MMA Blackbelt. She shared that her time as a Playmate “proves that if you do something with enough heart, integrity, and passion, good things will happen.”

The ninth Playmate offering one tempting apple bite

Bombshell beauty Brande Roderick stunned in her 2001 PMOY spread, temptation rolling off the pages just four years after she had packed up her life to pursue Hollywood dreams. Years of borrowing cars, sleeping on friends’ couches, and constantly searching for work had finally paid off. She shared “when I think about where I am now, I can’t believe where I started.” 

Our tenth Playmate in ruffles, floating light

Described by Playboy editors as “enigmatic” and “stunningly beautiful,” the captivating 1983 Playmate of the Year Marianne Gravatte was originally reluctant to accept her own beauty. After causing a few traffic accidents, she learned to be careful about making eye contact too readily. Above all, the most important thing to her was “Honesty. Without it, you have nothing.” 

The eleventh Playmate in with a Christmas glow

From Honolulu to Aspen to New York, the 1975 PMOY Marilyn Lange always carried the warmth of the islands with her. She described sex as “a deeper form of communication than some people realize” and a key benefit of “living in Hawaii is that you can make love outdoors… if you go to some of the outer islands, you find beaches where you don’t see anyone for maybe four, five hours. And you don’t hear anything but the birds.” 

And the twelfth Playmate all ready for winter snow

Raquel Pomplun’s journey embodied the American dream. Once a college student juggling a full course load and a demanding work schedule, she followed her instincts – and a bold piece of graffiti – straight into the spotlight. First, she landed a Playboy cover. Then she started hosting various shows and booking parts in two movies. From there, her rise to 2013 Playmate of the Year was the natural next step, where she shared that “Playboy taught me a side of myself I didn’t know before.”