Look back at Oprah's 1996 interview with John.
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."
Watch Oprah welcome John to her brand new set.
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."