Celebrity The 15 Most Iconic Playboy Covers of All Time By Isabel Jones Isabel Jones Instagram Twitter Isabel is an Oregon-born and Brooklyn-based writer and editor with a special interest in pop culture. InStyle's editorial guidelines Updated on September 28, 2017 @ 05:00PM Pin Share Tweet Email Photo: Playboy Archive Whether you count the late Hugh Hefner as a style icon, a sexual freedom pioneer, a pompous chauvinist, or a little of all three, there's no doubt the founder of Playboy Magazine has had a resounding impact on the fashion and pop culture landscapes. To remember the entrepreneur, who passed away yesterday at the age of 91, we've taken a look back at the 15 most iconic covers in Playboy history. VIDEO: Obit From Playboy: Hugh Hefner Dies at 91[brightcove:5591271210001 player_2] 01 of 15 Marilyn Monroe (December 1953) Courtesy of Playboy Behold, the first EVER issue of the magazine. Not a bad way to kick off a publishing legacy, if you ask us! 02 of 15 Darine Stern (October 1971) Playboy Archive In 1971, Playboy made history by featuring its first-ever African American cover girl. 03 of 15 Barbra Streisand (October 1977) Playboy Archive The legendary singer shocked both readers and fans when she appeared on the cover of the risqué 'zine. "What's a nice Jewish girl like me doing on the cover of Playboy?" the cover teased. 04 of 15 Farrah Fawcett (December 1978) Playboy Archive The iconic Charlie's angelrocked her signature shag and blinding smile on the magazine's December 1978 cover. 05 of 15 Madonna (Septmeber 1985) Playboy Archive The O.G. material girl cast off her belongings for a nude shoot with the famous men's mag. 06 of 15 Pamela Anderson (October 1989) Playboy Archive The longtime playmate put a NSFW twist on back-to-school on the cover of Playboy's October 1989 issue. 07 of 15 Donald Trump (March 1990) Playboy Archive Are you even surprised? 08 of 15 Anna Nicole Smith (June 1993) Playboy Archive The late Anna Nicole channeled Playboy's inaugural cover star as "Playmate of the Year" in 1993. 09 of 15 Jerry Seinfeld (October 1993) Playboy Archive The comedian is one of the few men to ever grace Playboy's cover. To this day, the issue remains one of the most valuable in the magazine's history. 10 of 15 Drew Barrymore (January 1995) Playboy Archive The child star caused quite the stir when she posed for Playboy at just 19 years old. 11 of 15 Cindy Crawford (October 1998) Playboy Archive The supermodel stripped down to just a tiny sarong for the pink and purple-hued cover. 12 of 15 Naomi Campbell (December 1999) Playboy Archive Campbell phoned it in for her Playboy Christmas cover—just kidding, but she *was* holding a phone (pre-cell, remember?). 13 of 15 Kim Kardashian (Pre-West) (December 2007) Playboy Archive In the early days of her reign, "Hollywood's New Sex Star" posed for a cover. 14 of 15 Marge Simpson (2009) Playboy The blue-haired Simpsons character stripped down for Playboy in 2009, recreating Darine Stern's 1971 cover. 15 of 15 Kate Moss (January/February 2014) Playboy Archive For the magazine's 60-year anniversary, Moss dressed the part as a classic Playboy bunny in a strapless leotard, bunny ears, a white shirt cuffs and collar, and some seriously badass black pumps.