Hugh Hefner, founder of the sprawling Playboy business empire, has died.
The 91-year-old had reportedly been battling cancer in secret for a number of years. In early May, reports said he had only weeks to live.
He died on Wednesday (local time), Playboy announced on Twitter.
"This is a very proud man who's spent his lifetime epitomising the sexual prowess of a red-blooded male," a source had told tabloid The National Enquirer earlier in the year.
"He'd rather be remembered as the virile stud with millions of hot girlfriends."
Hefner was born in 1926 into what he later called a "conservative, Midwestern, Methodist" family. He served as a writer during World War II, before studying psychology, art and creative writing.
He started Playboy magazine in 1953, his mother one of the first investors. It was an instant hit, the first issue selling more than 50,000 copies thanks to centrefold and cover star Marilyn Monroe.
During the magazine's glory years, Hefner claimed to be "involved with maybe 11 out of 12 months' worth of Playmates", as well as experimenting with bisexuality.
He divorced his first wife Mildred after 10 years of marriage in 1959. They had two children, including Christie, who would grow up to run the company for two decades.
His second wife was Playmate Kimberley Conrad, 36 years his junior. They married in 1989, and were married for 20 years - though separated for the last 11 - and had two kids. During the years they were separated Hefner had a number of girlfriends - often at the same time - including "number one" Holly Madison.
He married a third time in 2012 when he was 86 to 26-year-old Crystal Harris.
Playboy's circulation began falling in the 1970s, largely thanks to competition from rival pornographic magazine Penthouse, which often contained more sexually explicit content than could be found in Playboy.
In 1971 Hefner bought for US$1 million what became known as the Playboy Mansion. He sold it for US$100 million in 2016, on the condition he didn't have to move.
Hefner was an outspoken supporter of free speech and gay rights, and backed Barack Obama's reelection campaign in 2012. He also financially supported restoration of the famous Hollywood sign in the 1970s, and threw fundraisers for various causes, including animal rescue groups and the anti-vaccine movement.
He is expected to be buried next to actress Marilyn Monroe, who was the cover star and centrefold of the very first issue of Playboy in December 1953. He bought the vault next to hers in 1992.