Marilyn Monroe, who was featured in the first issue, was the only one to appear as "Sweetheart of the Month". The first model called a Playmate of the Month was Margie Harrison, Miss January 1954, in the second issue of Playboy. Generally a woman may only appear once as a Playmate, but in the early years of the magazine, some models were featured multiple times. Marilyn Waltz (February 1954, April 1954, April 1955 — her first appearance was as Margaret Scott) and Janet Pilgrim (July 1955, December 1955, and October 1956) are tied for the most appearances. Margie Harrison (January 1954, June 1954) and Marguerite Empey (May 1955, February 1956) are the only other women to appear more than once as Playmates.

     Under current law in most U.S. jurisdictions, publishing nude pictures of a model younger than 18 would be a felony. However, in the early years of the magazine, laws regarding corruption of a minor were less well established. Several playmates — including Nancy Crawford (April 1959), Donna Michelle (December 1963), Linda Moon (October 1966), Patti Reynolds (September 1965) and Teddi Smith (July 1960) - posed when they were seventeen. Elizabeth Ann Roberts (January 1958) - whose pictorial was called "Schoolmate Playmate" - posed when she was sixteen. Hugh Hefner and Roberts' mother were arrested as a result, but the case was subsequently dismissed because Roberts' mother had signed a statement that her daughter was eighteen before the photo shoot. In more recent years, Ursula Buchfellner posed for the German edition of Playboy when she was sixteen and subsequently posed for the American edition (October 1979) when she was eighteen. Gina Goldberg (May 1981), after emigrating from Finland, lied about her age and said she was 21 when she was really seventeen when she posed. Dutch Playmate twins Karin and Mirjam van Breeschootenappeared at age seventeen in their country's edition of Playboy in June 1988, at eighteen, they were Misses September 1989 in the US version. The youngest - i.e. last born - Playmate, as of June 2010 is Katie Vernola, born October 21, 1991.
     Prior to September 1959, Playboy did not ask Playmates to complete Data Sheets.

     Though most Playmates appear around an average age of 22, there are some women who became Playmates in their 30's. Dolores Donlon (August 1957), Janis Schmitt (February 1978), Eloise Broady (April 1988), Gillian Bonner (April 1996) and Tiffany Fallon (December 2004 and PMOY 2005) had turned 30 just before their Playmatehood. Bettie Page (January 1955), Susie Owens (March 1988), Arlene Baxter (December 1993) and Jaime Faith Edmondson (January 2010) were 31. Miss May 1985 Kathy Shower was a Playmate at 32, and at 33 became the oldest PMOY so far. Cindy Brooks (April 1985) and Julianna Young (November 1993) were aged 33. Since January 2003 Rebecca Anne Ramos is the oldest Playmate to date, appearing at the age of 35.

     In the 1950s, it was generally agreed that nude photographs were not pornographic unless they showed pubic hair. Respectable photography was careful to come close to, but not cross over the "line of decency." With Playmates, it was usually the case that the pubic area would be obscured by an item of clothing, a leg, or a piece of furniture. Eventually, after Playboy's rival magazine Penthouse had appeared (in 1965 in the UK), both magazines strove to show just a little bit more than the other, the so-called "Pubic Wars". A few more glimpses of pubic hair appeared in some pictorials and centerfolds, but it wasn't until January 1971 when Liv Lindeland, after 18 years and 216 issues, showed clearly visible pubic hair in her pictorial, generating a tremendous amount of media and popular attention. The first Playmate to clearly have the first full frontal nude centerfold was Miss January 1972, Marilyn Cole. Incidentally, both women went on to become Playmate of the Year.

     As the trend of playmates showing pubic hair continued through the following decades, it gradually brought along a styling of the pubic hair. The mid 1970s still saw a lot of "1970s Playboy" - natural and unstyled looks. During the latter half of the decade and the early 1980s, it evolved into a more attended "Bermuda triangle" and "Brazilian" style, which remained well into the 1990s. First seen in the mid '80s and common in the next decade, was the "landing strip," a small vertical patch, which even today can often be seen. Numerous stylings came to show at the end of the 1990s and into the 21st century. Eventually, in September 2001, Dalene Kurtis became the first Playmate to appear without any pubic hair. Other trends, started in the 1990s and more common today, are the appearances of body piercing, such as navel piercing, and tattoos.

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