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."