After his seven-year relationship with “No. 1 girlfriend” Madison ended, Hefner began dating Crystal Harris, whom he married on Dec. 31, 2012. In April, Hefner’s younger brother Keith died at the age of 87 from cancer.

Known for hosting its annual Playboy Halloween party, the Playboy Mansion sold to Hefner’s neighbor Daren Metropoulos for $200 million in June with the stipulation that Hefner was able to live in the home until his death.

In an August 2017 interview, Hefner’s son Cooper, who took over as chief creative officer of Playboy Enterprises, admitted that it was hard to watch his father get older.

“It’s tough to watch him struggle,” he told The Hollywood Reporter of his father getting older. “But I’m just happy it’s physical and not mental.

He is survived by his wife and four children.