1950s

By spring 1953, Hugh Hefner—a 1949 University of Illinois psychology graduate who had worked in Chicago for Esquire magazine writing promotional copy; Publisher's Development Corporation in sales and marketing; and Children's Activities magazine as circulation promotions manager—had planned out the elements of his own magazine, that he would call Stag Party. He formed HMH Publishing Corporation, and recruited his friend Eldon Sellers to find investors. Hefner eventually raised just over $8,000, including from his brother and mother. However, the publisher of an unrelated men's adventure magazine, Stag, contacted Hefner and informed him it would file suit to protect their trademark if he were to launch his magazine with that name. Hefner, his wife Millie, and Sellers met to seek a new name, considering "Top Hat", "Gentleman", "Sir'", "Satyr", "Pan" and "Bachelor" before Sellers suggested "Playboy".

The first issue, in December 1953, was undated, as Hefner was unsure there would be a second. He produced it in his Hyde Park kitchen. The first centerfold was Marilyn Monroe, although the picture used originally was taken for a calendar rather than for Playboy. Hefner chose what he deemed the "sexiest" image, a previously unused nude study of Marilyn stretched with an upraised arm on a red velvet background with closed eyes and mouth open. The heavy promotion centered around Marilyn's nudity on the already-famous calendar, together with the teasers in marketing, made the new Playboy magazine a success. The first issue sold out in weeks. Known circulation was 53,991. The cover price was 50¢. Copies of the first issue in mint to near mint condition sold for over $5,000 in 2002.

The novel Fahrenheit 451, by Ray Bradbury, was published in 1953 and serialized in the March, April and May 1954 issues of Playboy.

An urban legend started about Hefner and the Playmate of the Month because of markings on the front covers of the magazine. From 1955 to 1979 (except for a six-month gap in 1976), the "P" in Playboy had stars printed in or around the letter. The legend stated that this was either a rating that Hefner gave to the Playmate according to how attractive she was, the number of times that Hefner had slept with her, or how good she was in bed. The stars, between zero and 12, actually indicated the domestic or international advertising region for that printing.

1960s–1990s

From 1966 to 1976, Robie Macauley was the Fiction Editor at Playboy. During this period the magazine published fiction by Saul Bellow, Seán Ó Faoláin, John Updike, James Dickey, John Cheever, Doris Lessing, Joyce Carol Oates, Vladimir Nabokov, Michael Crichton, John le Carré, Irwin Shaw, Jean Shepherd, Arthur Koestler, Isaac Bashevis Singer, Bernard Malamud, John Irving, Anne Sexton, Nadine Gordimer, Kurt Vonnegut and J. P. Donleavy, as well as poetry by Yevgeny Yevtushenko.

In 1968 at the feminist Miss America protest, protestors symbolically threw a number of feminine products into a "Freedom Trash Can." These included copies of Playboy and Cosmopolitan magazines. One of the key pamphlets produced by the protesters was "No More Miss America!", by Robin Morgan which listed ten characteristics of the Miss America pageant that the authors believed degraded women; it compared the pageant to Playboy's centerfold as sisters under the skin, describing this as "The Unbeatable Madonna-Whore Combination."

Macauley contributed all of the popular Ribald Classics series published between January 1978 and March 1984.

Since reaching its peak in the 1970s, Playboy saw a decline in circulation and cultural relevance due to competition in the field it founded—first from Penthouse, then Oui (which was published as a spin-off of Playboy) and Gallery in the 1970s; later from pornographic videos; and more recently from lad mags such as Maxim, FHM, and Stuff. In response, Playboy has attempted to re-assert its hold on the 18–35 male demographic through slight changes to content and focusing on issues and personalities more appropriate to its audience—such as hip-hop artists being featured in the "Playboy Interview".

Christie Hefner, daughter of the founder Hugh Hefner, joined Playboy in 1975 and became head of the company in 1988. She announced in December 2008 that she would be stepping down from leading the company, effective in January 2009, and said that the election of Barack Obama as the next President had inspired her to give more time to charitable work, and that the decision to step down was her own. "Just as this country is embracing change in the form of new leadership, I have decided that now is the time to make changes in my own life as well," she said.

Post-2000

The magazine celebrated its 50th anniversary with the January 2004 issue. Celebrations were held at Las Vegas, Los Angeles, New York, and Moscow during the year to commemorate this event. Playboy also launched limited-edition products designed by a number of notable fashion-houses such as Versace, Vivienne Westwood and Sean Jean. As a hommage to the magazine 50th anniversary, MAC Cosmetics released two limited-edition products, namely a lipstick and a glitter cream.

The magazine runs several annual features and ratings. One of the most popular is its annual ranking of the top "party schools" among all U.S. universities and colleges. For 2009, the magazine used five considerations: bikini, brains, campus, sex and sports in the development of its list. The top ranked party school by Playboy for 2009 was the University of Miami.

In June 2009, the magazine reduced its publication schedule to 11 issues per year, with a combined July/August issue and on August 11, 2009. London's Daily Telegraph newspaper reported that Hugh Hefner had sold his English Manor house (next door to the famous Playboy Mansion) for $18 m ($10 m less than the reported asking price) to another American Daren Metropoulos the President and co-owner of Pabst Blue Ribbon. Also that due to significant losses in the company's value (down from $1 billion in 2000 to $84 million in 2009) the Playboy publishing empire is up for sale for $300 million. In December 2009, they further reduced the publication schedule to 10 issues per year, with a combined January/February issue.

On July 12, 2010, Playboy Enterprises Inc. announced Hefner's $5.50 per share offer ($122.5 million based on shares outstanding on April 30 and the closing price on July 9) to buy the portion of the company he did not already own and take the company private with the help of Rizvi Traverse Management LLC. The company derives much of its income from licensing rather than the magazine. On July 15, Penthouse owner FriendFinder Networks Inc. offered $210 million (the company is valued at $185 million), though Hefner, who already owned 70 percent of voting stock, did not want to sell. In January 2011, the publisher of Playboy magazine agreed to an offer by Hefner to take the company private for $6.15 per share, an 18 percent premium over the price of the last previous day of trading. The buyout was completed in March 2011.

2016–2018 changes and brief ending of frontal nudity

In October 2015, Playboy announced that starting with their March 2016 issue, the magazine would no longer feature full frontal nudity. Playboy CEO Scott Flanders acknowledged the magazine's inability to compete with freely available Internet pornography and nudity; according to him, "You're now one click away from every sex act imaginable for free. And so it's just passé at this juncture". Hefner agreed with the decision. The redesigned Playboy, however, would still feature a Playmate of the Month and pictures of women, but they would be rated as not appropriate for children under 13. The move would not affect PlayboyPlus.com (which features nudity at a paid subscription). Josh Horwitz of Quartz argued that the motivation for the decision to remove nudity from the magazine was to give Playboy Licensing a less inappropriate image in India and China, where the brand is a popular item on apparel and thus generates significant revenue.

Among other changes to the magazine included ending the popular jokes section and the various cartoons that appeared throughout the magazine. The redesign eliminated the use of jump copy (articles continuing on non-consecutive pages), which in turn eliminated most of the space for cartoons. Hefner, himself a former cartoonist, reportedly resisted dropping the cartoons more than the nudity, but ultimately obliged. Playboy's plans were to market itself as a competitor to Vanity Fair as opposed to more traditional competitors GQ and Maxim.

Playboy announced in February 2017, however, that the dropping of nudity had been a mistake, and furthermore for its March/April issue reestablished some of its franchises, including The Playboy Philosophy and Party Jokes, but dropped the subtitle "Entertainment for Men" inasmuch as gender roles have evolved. The announc