It is the golden hour in the Promised Land, and we are walking down Hallelujah Lane, going to see the Apostles. Only at Oprah’s house can one come up with a sentence like that as a literal description. Translation: It is a beautiful early evening in May, and Oprah and I are walking along one of the cobblestone lanes she has built on her 65-acre California estate, a startlingly beautiful landscape she calls the Promised Land. We are heading toward her favorite spot, where, under the shade of a spectacular live oak, she often lies on a chaise and reads. The tree is just one in a grove of twelve (the Apostles), and it is hard to tell where one tree ends and the next begins, their endless branches twisting and curling in a gorgeous, spooky tangle.
It’s no accident that this place is reminiscent of a Southern plantation. Right around the time her movie Beloved, the film adaptation of Toni Morrison’s Pulitzer Prize–winning novel, tanked at the box office in the fall of 1998—and after “Deliverance moved in next door” to her farm in Indiana—Oprah decided she needed to make some big changes, and so she began looking to buy an actual Southern plantation. Her fitness guru Bob Greene was scouring for such a place when he stumbled on this property: 42 acres of paradise perfectly situated between the Santa Ynez Mountains and the Pacific Ocean. (Last year, when her neighbor died, Oprah outbid a developer for another 23 acres.) Oprah bought it in 2001 and began a five-year construction and landscaping project—managed by Greene—that included planting a forest of mature oaks and building a fountain the size of a lake that shoots water to the heavens.
“I was calling it Tara II,” says Oprah, “and one day Bob and I were walking around the property and he said, ‘Scarlett O’Hara wishes she had this. Scarlett was not living like this.’ So he goes, ‘You need a better name. The fact that you are an African-American woman from Mississippi and you get to have this . . . it’s deep.’ So I go, ‘Yeah! It’s like a dream.’ And he’s like, ‘Yeah! It’s a promise! It’s the Promised Land!’ So I feel that every day. I don’t know of a person who can honestly, deeply, profoundly speak to the word contentment. I’ve tried to talk to other people about this thing: I have no angst. No . . . nothing. No regret, no fear. I mean . . . just absolute joyful contentment.”
When I first arrived around lunchtime, a handsome fellow in a golf cart—Oprah’s head of security—appeared at the gate to take me to the house, and as we bumped along the cobblestones, her enormous neo-Georgian mansion came into view. We passed workers on other golf carts, men clipping hedges, an elaborate formal rose garden, a pond with ducks. He deposited me in the house in a room off the kitchen, where a small army of women in uniforms scurried in and out. Someone offered me a sandwich, which was served with a place setting of vintage silverware, a Venetian water glass, and a beautiful linen napkin with a hand-embroidered O.
I heard a rustling in the kitchen, and suddenly Oprah appeared from around a corner in a bathrobe and slippers. The photo shoot with Annie Leibovitz was running long, and she didn’t like that we had not yet said hello. “Annie was saying, ‘I hope I’m not keeping you from Jonathan,’ ” she says. “I go, ‘I’m not worried about Jonathan. Because I can only concentrate on being here with you right now. And then when I’m with Jonathan, I will be with Jonathan and I won’t be thinking about you!’ She let out a big laugh and, as she was walking away, said, “I have learned that being-fully-present thing. I am 1,000 percent fully present.”
When the shoot is finally over, I am taken to the teahouse, a romantic, open-air stone structure Oprah built for the sole purpose of reading The New York Times in the morning while drinking her tea. There are orchids everywhere, stacks of gardening books, and voluminous green wicker sofas and chairs. The first time I interviewed her for this magazine was in 1998, when I spent three summer days hiking in Telluride with Oprah, her best friend and colleague Gayle King, and Bob Greene as Oprah was getting ready for the press rollout for Beloved and her Vogue cover shoot, for which she was training and dieting to lose 20 pounds. The hikes were brutal; the meals afterward, cooked by her then-chef, Art Smith, spartan. I was not there to lose weight but came home several pounds lighter. During one of those hikes, I asked if she had ever imagined she’d be on the cover of Vogue. “Dreamed to be in Vogue? I’m a black woman from Mississippi . . . I would never have even thought of it as a possibility . . . I’ve been fighting weight all my life, definitely never even thought of myself as an attractive girl.” She laughed. “So why would I be dreaming about Vogue? Vogue is the big house! Didn’t think I’d be sittin’ at that table!”
Read more at Vogue.