The two shared a laconic sense of humour, similar interests, and an apparent spiritual connection. In 2003, Madison was invited to move into his room (with its famous revolving bed) in a newly created role as his "No 1" girlfriend.
According to Hefner, their relationship developed into a deep and genuine love affair.
Though he never gave up his other girlfriends (Madison never asked him to), friends and acquaintances concur.
Steven Watts, a professor of history at the University of Missouri who last month published Mr Playboy, a biography of Hefner, says that for five years Madison has represented to Hefner something akin to wife, mother and lover combined. I've been feeling like roadkill." The tragedy of the situation is that Hefner's promiscuous private life, for so long a source of great personal pride, could now have contributed to him losing the one person capable of making him truly happy.
"We tried to have a baby earlier this year and it didn't work out. "He may not believe in monogamy in the traditional sense of the term, but deep down, Hef is a romantic," Watts says.
"What he really likes more than sex is falling in love over and over again, in a sentimental way.
"The mansion's hedonistic grounds have long been rented out for corporate events, but Hefner's private parties have been free to those invited," it reported.
"Now, John and Jane Q Public can buy their way into some of those events - albeit for a hefty price." Tickets to parties hosted by Hefner will sell for ,000 (£2,870) to ,000, it reported, depending on the event and the celebrity guests.
The second great creation, Hefner says, is his own life: a roller-coaster of fame, fortune and willing blondes played out against the backdrop of 10236 Charing Cross Road, the 1920s pile on the outskirts of Beverly Hills that he calls home, but which the rest of the world knows as the Playboy Mansion. And, although Hefner has never been one to blow his own trumpet, his enduring ability to perform in both the boardroom and the bedroom (even as he approaches his 83rd birthday!
) has elevated him to the status of national treasure. In recent weeks, the institution that is Hugh Hefner has been rocked by a string of public and private setbacks that have conspired to throw this elderly, somewhat deaf and increasingly frail man back into the public eye, for all the wrong reasons.
All, however, boil down to a single problem: Hefner's aura of Gatsby-esque sophistication is ever more at odds with his advancing years, and a changing world.