Celebrities and former Playboy cover stars are leading the tributes to magazine founder Hugh Hefner, after his death aged 91.
The publishing magnate founded Playboy Magazine in 1953 after saving $8,000 to put the first issue together, which featured an old nude photo of Marilyn Monroe - the first centrefold.
Hefner made several film and TV cameos and was credited with boosting the careers of some of the most famous names in popular culture.
Nancy Sinatra tweeted a photo of her with "Hef" and wrote: "One of the nicest men I've ever known. Godspeed, Hugh Hefner."
Actor Mark Hamill wrote: "1st met him months B4 #SW opened-expected stereotyped swinger/wildman not the kind-thoughtful loyal friend he always was the ML & me."
Kim Kardashian, who appeared on the cover of Playboy in 2007 to promote her show Keeping Up With the Kardashians, tweeted: "RIP to the legendary Hugh Hefner! I'm so honoured to have been a part of the Playboy team!
"You will be greatly missed! Love you Hef! Xoxo."
Kiss frontman Gene Simmons wrote: "A great man, entrepreneur and innovator. Your legacy lives on. #Hef."
Ryan Seacrest tweeted: "Rest in peace #HughHefner - he will forever be remembered as the Hollywood legend who lived life to the fullest."
Hefner died at the Playboy Mansion aged 91, of natural causes.
A spokesperson confirmed in a statement: "Hugh M. Hefner, the American icon who in 1953 introduced the world to Playboy magazine and built the company into one of the most recognisable American global brands in history, peacefully passed away today from natural causes at his home, the Playboy Mansion, surrounded by loved ones."
