Hugh Hefner developed a reputation in his life for being a hard-partying womanizer, and an intellectual who sparked a revolution by founding Playboy magazine.
But when the FBI conducted secret surveillance on Hefner in the 1950s, they found something that may be even more shocking --- he was actually boring, and seemed a bit lonely.
As the Calgary Herald noted, the FBI recently released its case files on Hefner following his death in 2017. The bureau was investigating the accusations of obscenity after the 1953 launch of Playboy, and allegations that Hefner may have actually been using the magazine as cover to secretly photograph and film women in order to traffic obscene material across state lines.
A tipster had told the FBI that Hugh Hefner was holding wild parties in Chicago on an almost weekly basis, with some raging through the entire night. The FBI dispatched an agent to track Hefner's apartment for seven straight nights.
They found that Hefner went out by himself and turned in early, with the agent noting that he seemed a bit lonely.
"On May 13, 1958, [Special Agent Harold Brown] noted in his report, Hefner emerged at about 6:45 p.m. and walked three blocks to a restaurant where he ate dinner and then returned and turned off his apartment lights for the night," the report noted. "No other activity from his surveillance is noted."
While the finding may have been unusual, the next turn in the investigation was even more strange. Hefner was somehow tipped off to the FBI investigation, and made an unusual decision -- he called Brown directly and invited the FBI agent into his office. There, Hefner spoke about his plans to move to a new location that led to repeated arguments with a landlord, who may have been the FBI's tipster.
Hefner denied making so-called "stag films" and said there was never any untoward conduct at the magazine's offices.
"Hefner stated that he has been accused of having wild parties in the offices of 'Playboy' but he emphatically denied any party activities at this address and stated that he occupies sleeping quarters at the rear of his office on the 4th floor," the FBI files noted.
As the New York Daily News noted, Hefner would later be arrested on charges that he published "obscene and suggestive" photos of Jayne Mansfield. He was ultimately acquitted.Plenty about the Playboy founder seemed to change after his FBI interview. At the time, Hugh Hefner told the FBI agents that despite employing a number of "young girls" at the magazine, he did not want to date any of them because he was afraid it would "cast a bad reflection" on the magazine.