Born just days after his father was elected president of the United States, John F. Kennedy Jr. has been famous since the day he entered the world. Family photos of his childhood spent playing under the desk in the Oval Office are part of his family's Camelot story. His glamorous girlfriends and selection as the only non-actor ever to be People magazine's "Sexiest Man Alive" drive tabloid sales through the roof.
Is there a better guest to kick off the 11th season of The Oprah Winfrey Show? "I've waited all my life to interview John-John!" Oprah says.
While his childhood is part of American history, John says his memories of that time and his dad are fleeting. "I remember he used to call me Sam to annoy me, and I remember getting kind of upset. I'd say: 'My name is not Sam. It's John.' 'Oh, sorry, Sam.' 'My name is not Sam,'" he says. "I remember that, but, you know, I was quite young."
As the most prominent heir to the Kennedy family's fortune and name, John is probably the closest thing to royalty in America. Yet, despite their great wealth, John says his family places great emphasis on working. After graduating from Brown University, John helped various Kennedy family charities. After law school, he worked as a prosecutor in the Manhattan district attorney's office. These days, John is the co-founder and editor-in-chief of George, a new political lifestyle magazine that recently published its seventh issue. While reading some political magazines feels like attending a public policy lecture, George strives to make politics hip. Its tagline is: "Not Just Politics as Usual."
George's namesake is George Washington, and each issue's cover references our first president's iconic image. The magazine's "inaugural issue" featured a photo of supermodel Cindy Crawford dressed in a wig and Revolutionary War–style military coat...and an exposed midriff!
"If you're trying to talk about public issues and politics and showcase it in a positive, different way, I think people like the idea," John says. "My partner and I, Michael Berman, we had an idea, but we didn't know quite how it would show in the real world."
It's clearly working—George is already the largest-selling political magazine in the country.
One of the reasons for George's success, John says, is that it taps into an underserved demographic. "Women buy about 85 percent of magazines, but they buy about 8 percent of political magazines. And 57 percent of our readers are women," he says. "Women are the fastest-growing segment of voters."
Some pundits have even called the 1996 election the year of women in politics. "They've defined the political year, [from] the relationship between Bob Dole and his wife and Bill Clinton and his wife," John says. "And the keynote speaker of the Republican convention was a woman."
To honor this sea change, the September 1996 issue of George profiles 20 of the most fascinating women in politics, including Hillary Clinton, Terry McMillan and Barbra Streisand.
While she's not as well known as these big names, California state legislator Sheila Kuehl is as fascinating as they come. Not only did Sheila portray the brainy Zelda on the 1960s sitcom The Many Loves of Dobie Gillis, she is also the first openly gay assemblywoman in California history.
In the statehouse in Sacramento, Sheila works on issues like child support and help for battered women. She says the feature in George has changed her career. "Last week, I spoke at the Democratic Convention on domestic violence, and that is an enormous honor," she says. "People start to pay attention to you when George pays attention to you."
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."
John says he's always relied on his sister, Caroline Kennedy Schlossberg, even though she did boss him around when they were younger. "We're obviously very close. As a younger brother, you look up to your sister. I was the 'man' of the family, as it were," he says. "I feel so lucky that I have such a close relationship with her."
Like John, Caroline has also worked in publishing. She interned for the New York Daily News and wrote for Rolling Stone. With Ellen Alderman, Caroline co-authored the 1995 book The Right to Privacy.
John says the clash between privacy and fame is a topic he and his sister know all about. "We're used to a certain degree of being watched," he says. "I understand that there's interest, and certainly that interest has given both of us great opportunities, so I can't complain too much. Sometimes I wish it wasn't always that way, but then you wouldn't have invited me on your show if I was just somebody else."
Oprah is no stranger to the Kennedy family. While working for a TV station in Baltimore, she befriended John's cousin Maria Shriver—her mother, Eunice, is a sister of John, Robert and Ted Kennedy.
Once while visiting the Kennedy family home at Cape Cod for a party in Maria's honor, Oprah even struck up a conversation with John's mother, Jackie. "Your mother was behind the counter serving clam chowder," Oprah says. "And we sat down and we had a really wonderful conversation about life."
Oprah says she always dreamed of interviewing Jackie—but the former first lady stayed out of the media spotlight until she died in 1994. John says there was no grand decision behind his mother's silence. "It was just her life was easier if she lived it privately. And once you start answering those questions, then where do you stop with it?" he says. "It was a practical consideration that made more sense for her."
In April 1996, Sotheby's Auction House hosted the sale of the century—an auction of items from the estate of Jacqueline Kennedy Onassis. Public interest in the auction was huge, and the media covered it with the intensity of a sporting event.
The entire sale brought in a reported $34.5 million—more than 10 times what organizers had anticipated. John says the overwhelming interest of the public surprised him. "We didn't really know what to expect," he says.
Many observers expressed shock that Jackie's children could part with the nearly 1,300 items up for sale, including personal letters, furniture, artwork, jewelry, trinkets and a set of President Kennedy's golf clubs. John says he and his sister, Caroline, decided the auction was needed after their mother died in 1994 and they realized all that was left behind. "My mother kept every single thing that she ever got in her life. Either we were going to open up a museum or we were going to have more normal lives," John says. "We have the things that really matter and we really valued and [were] really evocative of our mother. And that's what important."
What are two questions everyone wants to ask John? First, will he ever join the family business run for office?
"I certainly thought about it. I really grew up in a political environment," he says. "And it was important to do something different. John Adams said that you should become a politician at the end of your life when you bring a wealth of life experience to bear on that office. I was eager to try something different, to see another part of life."
Second, when is he getting married? But Oprah says she purposely did not ask this one. "Because it's the number one question everybody asks me!" she says. "And I don't think it's anybody's business but his."