Now she is 63. What I want to know is: What does 63 know that 44 didn’t? She pauses for a long time. “In your 40s, you’re coming into it, you’re intellectualizing things, and you kind of know it and you feel it,” she says. “But there is a deepening and a broadening and quickening of the knowing that happens in your 50s. Maya Angelou used to say to me, ‘The 50s are everything you’ve been meaning to be.’ She looks at me over the top of the nerd-chic glasses she favors these days. “You’d been meaning to be that person.” She laughs. “By the time you hit 60, there are just no . . . damn . . . apologies. And certainly not at 63. And the weight thing that was always such a physical, spiritual, emotional burden for me—no apologies for that either.”

Interviewing people who interview people for a living presents a special challenge: They know what you’re up to. You feel as if you’re being quietly judged. Not with Oprah. Once she’s committed, once she’s present, there is a kind of flow and trust that develops on the spot. Oprah, by her count, has interviewed more than 37,000 people during her 25 years of doing the The Oprah Winfrey Show in Chicago. When I ask her if there is one big takeaway, she says, “Absolutely. There’s not a human being alive who doesn’t want—in any conversation, encounter, experience with another human being—to feel like they matter. And you can resolve any issue if you could just get to what it is that they want—they want to be heard. And they want to know that what they said to you meant something. Most people go their entire lives and nobody ever really wants the answer to ‘How are you? Tell me about yourself.’ And what was so beautifully . . . what is the word? . . comforting about what happened every day on the Oprah show is that people would dress up like they were going to church. Sometimes I would notice somebody and I would say, ‘Oh, wow, that’s a really pretty green dress.’ And she would go: ‘I wore it for you! I knew you would notice me!’ People just want to be seen; they want to be validated.”

~ Jonathan Van Meter, from Oprah Winfrey Is On a Roll (Again) in Vogue, August 15, 2017

Portrait of Oprah by Annie Leibovitz, Vogue, September 2017 titled: “Like a Prayer.” “I have no angst, no regret, no fear,” Oprah says.