To mark what would have been John F. Kennedy Jr.'s 50th birthday, Oprah is reflecting on the life of this American icon and their once-in-a-lifetime conversation in 1996. "Today we are honoring his memory by looking back at the life, the legacy and the tragic death of America's prince," she says.
The interview with John was the 11th season premiere of The Oprah Winfrey Show, and it was big news. John had just delivered a speech introducing his uncle Sen. Ted Kennedy at the 1996 Democratic National Convention. In addition, the gossip pages were ablaze with John's recently announced engagement. "It was a very exciting day because John F. Kennedy Jr. didn't sit down and talk to anybody," Oprah says. "We'd been on the air for 10 years and had been trying to get him to talk, and only I think because he was releasing his magazine, George, was he willing to do it. It was still a huge, huge, huge coup for all of my team to talk him into saying yes."
After rewatching the interview for the first time in years, Oprah says John's character impressed her all over again. "He is more timeless than ever. He is statuesque. He has such wonderful presence. He feels calm," she says. "Even though I know that he was nervous, he feels in control."
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.
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."
While working for a TV station in Baltimore, Oprah made a lifelong friend in Maria Shriver, who is one of John's cousins. Oprah even has been invited to visit the famous Kennedy compound in Hyannis Port, Massachusetts!
Oprah told John how, at a party held in Maria's honor, she once struck up a conversation with his 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."
The interview with John not only marked the beginning of The Oprah Show's 11th season, it was also the first—and only—time a guest sat in her brand new linen chairs. "At the end of that interview, I remember John standing up and saying, 'Oh, look, I've got lint all over me.' I was mortified," Oprah says. "We rushed out and had those very chairs covered in leather and we used those for years."
These reupholstered leather chairs remained on Oprah's set until they were auctioned off in an Angel Network fundraiser. The winning bid of $64,000 was submitted by a former co-worker of Oprah's from her days anchoring the news Nashville!
Less than three weeks after Oprah's conversation with John aired, he and his fiancée, Carolyn Bessette, were married in a top-secret wedding on a remote island off the coast of Georgia. John's love life had always been fodder for tabloids, and his marriage was the subject of constant gossip, yet Oprah never brought it up during the interview.
Oprah says the Kennedy family's ability to keep media away from the wedding was an incredible feat. "Every tabloid in the world would have been there with helicopters and photographers and would have ruined that moment for him," Oprah says. "What that means is that he had to be surrounded by some people who he really trusted who didn't sell him out."
On July 16, 1999, John F. Kennedy, Jr.; his wife, Carolyn; and her sister, Lauren Bessette, boarded a small airplane piloted by John. They were set to fly from New Jersey to the Kennedy family home in Hyannis Port, Massachusetts, for a wedding.
Hours later, the news broke that their light aircraft had gone missing and rescuers were on the scene. Oprah watched the unfolding tragedy from her farmhouse in Indiana. "I remember sitting, just like most of you, glued to the television," she says. "Hoping, praying that they were going to show up on an island somewhere."
Almost a week later, the news came that the plane's wreckage had been found and there were no survivors.
Oprah says she has thought often about the deaths of John, Carolyn and Lauren. "I know that all death is here to teach us about life," she says. "It made me think about ... how to live more presently in the now."