When Hugh Hefner’s death was announced late last night, it shouldn’t have surprised people. After all, the Playboy founder was was 91, and had been keeping a low-profile for years, leaving the magazine to his youngest son, Cooper. But the Twitterverse reacted in shock, no doubt assuming he would somehow always be found partying in the grotto.
Hef might be gone, but his memory lives on in the A-list stars he convinced to cover his magazine over the years. Naturally, most of them took to Instagram to share their condolences for the late icon. Paris Hilton, Kim Kardashian, Cindy Crawford and The Girls Next Door star Bridget Marquardt all shared snaps with Hefner. There’s been no word yet from Holly Madison, his number one girlfriend for a time, whose scathing expose on life in the mansion is infamous.
Scroll through for a look back at his most notable celebrity covers, from a photo of Marilyn Monroe taken for rent money to 68 pages devoted to a 39-year-old Kate Moss.