
The magazine is well-known for two publicity stunts - offering Charles, Prince of Wales $45,000 to appear nude in a centerfold in 1990, and publishing a nude pictorial called "The Men of Enron" in September 2002 in which some former Enron employees "lost their shirts."
Though the magazine is marketed to heterosexual women, Playgirl's then-editor-in-chief Michele Zipp said in 2003, "The gay readership is about 30%." She went on to add, "It's 'Entertainment for Women' because there's no other magazine out there that caters to women in the way we do, but we love our gay readers as well."[1] Also in 2003, the President of Trans Digital Media, LLC (the brand management firm for Playgirl TV), Mark Graff, stated that 50% of Playgirl's readership are gay males.

Throughout the history of the magazine, Playgirl has featured male frontal nudity except for the early issues in 1973, and the infamous non-nude year 1987. In 1986, Drake Publishers (later renamed Crescent, and renamed again to Blue Horizon Media) bought Playgirl and relocated it to New York. John Paul became the first full frontal centerfold in November 1987 after a disastrous non-nude year. Throughout the years the magazine has matured as erections, foreskin and non-Caucasian models have appeared in the magazine. The magazine has generally featured models who have been circumcised but of late, layouts with uncircumcised models are featured.

Apart from professional models, Playgirl features amateur models in a section called Real Men (formerly known as Snapshots). A Real Men of the Year contest is held, in which readers can vote the for the best layout of the year.
Every year in June, Playgirl has its "Man of the Year" issue. In July, it's the "Country" issue and in November, Playgirl dedicates an issue to "Campus Hunks." A nude centerfold calendar featuring the men of the previous year is usually included in the December or January issue of the magazine. Readers are asked to vote for the Man of the Year from the pictures of the calendar.
Last August 2008, the magazine announced that they will cease publication of its print edition as of the January 2009 issue. After that point, the magazine plans to continue with an online-only edition
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