May has always been a month associated with sunshine, celebrations, outdoor gatherings, and the anticipation of summer. From Cinco de Mayo and Mother's Day to Memorial Day in the United States, the month brings plenty of reasons to enjoy the warmer weather and spend time outdoors.
For fans of classic men's magazines and glamour modeling, May also has a special place in Playboy history. Over the years, numerous models have appeared as the magazine's Playmate of the Month during May, creating memorable covers and pictorials that remain part of pop-culture history.
We've revisited some of the most recognizable May Playmates from different eras and ranked ten of the most memorable names. From legendary stars to models who went on to build careers in television and entertainment, these women each brought something distinctive to their Playboy appearances.
10. Sasha Bonilova – 2011
Sasha Bonilova became Playboy's Playmate of the Month for May 2011. Born in Ukraine, she moved to the United States as a teenager and eventually established herself in the modeling world.
Known for her blonde hair and striking green eyes, Sasha quickly attracted attention with her glamorous appearance. Her journey into modeling was not always straightforward, particularly because her traditional family initially had reservations about her decision to pose for Playboy.
Outside modeling, Sasha has described herself as something of a tomboy. She has a passion for motorcycles and sports, giving her personality a more adventurous side beyond her glamorous image.
9. Kristen Nicole – 2013
Kristen Nicole brought classic California glamour to the May 2013 Playboy cover. The Southern California native had already developed an impressive modeling résumé before her Playboy appearance.
With her blonde hair, blue eyes and beach-inspired look, Kristen was a natural fit for the magazine's summer-oriented aesthetic. She had also worked with recognizable names and brands in the entertainment and fashion industries, including Guitar World and Paul Mitchell.
Her Playboy opportunity arrived remarkably quickly. Following her initial photo shoot, she was selected for the May cover, making her appearance a notable milestone in her modeling career.
8. Nikki Leigh – 2012
California native Nikki Leigh became the May 2012 Playmate and used the opportunity as another step forward in a growing entertainment career.
Her blonde hair and California beach style made her a natural fit for the Playboy brand. Following her appearance, Nikki expanded her résumé beyond modeling with appearances in television and film.
Among her acting credits are appearances connected with shows such as Two and a Half Men and Tosh.0, along with roles in movies including The Wedding Ringer. Her career demonstrates how a Playboy appearance could serve as a launching point for further entertainment opportunities.
7. Brook Power – 2016
Brook Power was Playboy's Playmate of the Month for May 2016. Born in Southern California and raised in Oahu, Hawaii, she developed a strong connection with the ocean and an active island lifestyle.
Surfing and spending time near the water were important parts of Brook's life. Her distinctive look also reflected her Native American heritage, adding another dimension to her modeling identity.
Beyond modeling, Brook has spoken about art, independence and gender equality. Her interests and perspective helped make her May 2016 appearance stand out from the traditional glamour-model profile.
6. Laurie Fetter – 2003
Chicago-born Laurie Fetter became the May 2003 Playmate and brought a classic American glamour style to the pages of Playboy.
With blonde hair and blue eyes, Laurie also had interests that extended well beyond modeling. She was known for her enthusiasm for football and had ambitions of building a long-term career as an actress.
Her approach to the entertainment business was refreshingly realistic. She recognized that modeling and acting could be unpredictable careers, while remaining determined to continue working in entertainment.
5. Crystal McCahill – 2009
Crystal McCahill made Playboy history in May 2009 by becoming part of a unique family connection. Her mother, Gale Olson, had previously appeared as Playboy's Miss August in 1968.
That connection gave Crystal a particularly interesting relationship with the magazine. She had grown up familiar with Playboy through her mother's experience and eventually followed a similar path herself.
Born in Illinois and spending part of her childhood in Hawaii, Crystal also had an unusual background that included attending a Japanese school. After Playboy, she continued exploring opportunities in film and television.
4. Deanna Brooks – 1998
Deanna Brooks was named Playboy's Playmate of the Month for May 1998. Her path to the magazine was quite different from the typical entertainment-industry story.
Before becoming a Playmate, Deanna worked in banking and helped customers with financial planning and savings. Her life changed dramatically after her Playboy pictorial was published, and she ultimately lost her banking position.
Despite the professional consequences, Deanna stood by her decision. Her story remains one of the more unusual examples of how appearing in a major men's magazine could have a profound impact on a model's career and personal life.
3. Dani Mathers – 2014
Dani Mathers quickly established herself as one of the recognizable Playboy personalities of the 2010s. Her connection with the magazine began before she appeared on its cover, when she was selected as Cybergirl of the Month in 2013.
The following year brought an even bigger opportunity when Dani became the May 2014 Playmate. Her popularity continued to grow, and she was subsequently selected as Playmate of the Year for 2015.
Her California background, modeling experience and energetic personality helped her stand out during her time with Playboy. She later continued to attract attention through television and entertainment appearances.
2. Brooke Berry – 2000
Canadian model Brooke Berry earned the May 2000 Playmate title and became another memorable Canadian presence in Playboy's long history.
Born in Vancouver, Brooke later moved to Northern California. Her lifestyle was strongly influenced by the outdoors, particularly the mountains and natural surroundings around the Sierra Nevada region.
Although Los Angeles offered the excitement of the entertainment industry, Brooke remained drawn to the quieter mountain lifestyle. That combination of glamour and an outdoors-oriented personality made her an interesting addition to the Playboy lineup.
1. Anna Nicole Smith – 1992
At number one is Anna Nicole Smith, one of the most recognizable personalities ever to emerge from Playboy.
When she appeared as the May 1992 Playmate, Anna Nicole was still at the beginning of what would become a highly publicized career. Her glamorous blonde appearance and classic hourglass silhouette immediately attracted widespread attention.
Her Playboy exposure helped launch her into a much larger world of modeling, television and celebrity culture. She later became internationally known for her marriage to billionaire J. Howard Marshall, her television appearances and her highly publicized personal life.
Although her life and career eventually became surrounded by controversy and tragedy, her 1992 Playboy appearance remains one of the defining moments of her early career.
Final Thoughts
From the early 1990s through the 2010s, Playboy's May Playmates represented several different eras of glamour and popular culture. Some built careers in modeling, others moved into acting and television, while a few became major celebrity personalities.
Anna Nicole Smith remains the standout name on this list because of the enormous cultural impact she eventually achieved. But every woman featured here contributed her own story to Playboy's history.
Which May Playmate would you rank at number one? Share your favorite in the comments.