John says he embraces both the challenges and opportunities of his family's legacy. "There is this great weight of expectation and anticipation," he says. "Part of you wants to address that in some way and maybe do something different, but also just to engage it."
One way he has engaged his family mythology is on the cover of the September 1996 issue of George—it features Drew Barrymore, dressed as Marilyn Monroe, wishing President Bill Clinton a happy 50th birthday. This cover evokes the time Marilyn—who allegedly had an affair with JFK—sang a sultry rendition of "Happy Birthday, Mr. President" to John's father at Madison Square Garden on his 45th birthday in 1962.
John says he doesn't expect this tweaking of family history to upset any of his relatives. "My family is used to all manner of controversy," he says. "In the grand scheme of things, this probably didn't register too high on the Richter scale."