As co-founder and editor-in-chief of the hip political magazine George, John was one of the hottest names in the late-1990s publishing world. John told Oprah he was happy to engage the family's legacy—both the famous and the infamous—sometime on the cover of the magazine.
Watch John tell Oprah about the early days of George.
The September 1996 issue of George featured Drew Barrymore, dressed as Marilyn Monroe, wishing President Bill Clinton a happy 50th birthday. This cover was a wink to the time Marilyn—who allegedly had an affair with JFK—sang a sultry rendition of "Happy Birthday, Mr. President" to John's father on his 45th birthday party at Madison Square Garden.
John told Oprah he didn't expect to feel much grief from his relatives about this gag. "My family is used to all manner of controversy," he said. "In the grand scheme of things, this probably didn't register too high on the Richter scale."