From the Archives: Oprah Winfrey in Vogue (1998)

Photographed By Steven Meisel

READY FOR HER CLOSE-UPWearing a black corset dress under a golden brocade kimono, both by Dolce & Gabbana.

PROFILE OF GREATNESS “What I have decided,” a forward-looking Oprah says, “is that with fame, notoriety, credibility—if you can’t have the courage to stand up and speak out for what you truly believe in, then it means nothing.”
Strapless scarlet-silk bustier by Giorgio Armani. Cross and chain by Jean Schlumberger for Tiffany & Co.

BELOVED WOMENFrom left: Kimberly Elise in an Isaac Mizrahi dress, Oprah in Valentino Couture corset and long skirt with fringe, and Thandie Newton in Isaac Mizrahi.

Silk halter and long skirt by Giorgio Armani. Earrings and bracelet by Fred Leighton New York.

Source: VOGUE



  1. After reading the poorly crafted abomination by Helen S. Garson (Oprah Winfry: A Biography), I sought additional resource material to further unravel the enigma of a personality that was only hinted at in Garson’s book. The first source I tried, a book by her erstwhile boyfriend and “escort for life,” Stedman Graham (“You Can Make it Happen”), the puzzle that is Oprah was ignored altogether. Stedman’s book, it turns out was a motivational tract aimed mostly at young black men. And while interesting, except for a few disclaimers, was altogether mute on the issue of Oprah her self. While this book began honestly enough, at least in the early chapters, using Oprah’s sister Patricia Lee’s revelations to begin pulling back the veil slightly, most of the rest of the book, like Garson’s, was again poorly organized and devoted to issuing lavish, endless and sometimes unwarranted praise of Oprah’s accomplishments. This incessant and sycophantic praising gets tiring very quickly, and in the end serves more to mask and turn Oprah into a one-dimensional caricature of herself than to reveal “the real” Oprah. Without being mean-spirited in anyway, one could certainly argue that there is hardly any further need for another book devoted to praising Oprah’s achievements since they are all on public display daily via her TV show, in her overt support of President Obama, her many public awards, and in her support of the South Africans Girl’s school, which she never misses an opportunity to gush about.

    Two of Oprah’s best friends Quincy Jones and Maya Angelou, also had troubled childhoods that they both wrote about eloquently and honestly. For them, giving an honest portrayal actually seemed to have enlarged rather than subtracted from their stature. By attempting to conceal her troubled past, one fears that Oprah has done just the opposite, and in the process done herself more long-term harm than good: For it is one thing to be a troubled child with an embarrassing background, and quite another to lie about it — although most of us do lie about unpleasant aspects of our past. However, it takes a different kind of character flaw (on an altogether higher dimension) to seek to enlist the rest of the world in a cover-up of these unpleasant facts, and expect them to keep the secret for life. And then to get passive aggressively incensed when they refuse to participate in the cover-up for life. That is what Oprah did. One now wonders what additional secrets Stedman is holding back for later strategic revelations? All Oprah has done has been to make herself vulnerable to more hidden longer stemmed time bombs, all of her own making.

    Until this book, what seemed to have been missing from Oprah’s biography was the “Rosetta Stone” to her personality and character: a clearing up of and a “squaring of the ledger” for the period of her life from the ages of about 10 to15. Until her sister had her say in the present book, that phase had been carefully shrouded in self-made legend and purposeful mystery. And frankly the earlier book by Ms. Garson, by clumsily trying to obfuscate and hide that period, simply raised the alarm as well as the stakes, making it all the more important to see behind Oprah’s carefully constructed screen. That is what motivated me to pursue the issue further.

    Much to Ms. Winfry’s dismay, Patricia Lee, Oprah younger sister, no longer wanted to be a party to the lie and the sloppy cover-up. So she went public in this book, intentionally destroying the cheesily concocted legend about Oprah during this critical period of her life.

    According to Ms. Lee, Oprah was a smart but promiscuous, thieving, little out-of-control, entitled bitch, who wreaked so much havoc in their Milwaukee household during the ages of about nine until 13 that her mother sought to have her committed to a girl’s reformatory. Had the school not been overcrowded at the time, the Oprah Winfry story may have had a very different ending. But fortunately for Oprah, while waiting to be admitted to the Reform School, Oprah’s mother decided instead to foist her off on her father in Tennessee. He carted her back to Knoxville where it was discovered that she was already several months pregnant. Vernon Winfry, as much as it could be done, put a stop to Oprah’s lying, thieving and whoring ways, and almost made a respectable lady out of her. In any case, after the baby died under mysterious circumstances, Oprah’s life changed for the better. She stole a couple of beauty contests, and ended up with an offer to co-anchor a TV news program, and the rest is history.

    My sympathy lies with Oprah. Her’s was a very heavy cross for an American celebrity to have to bear. If it were mine, I would have lied about her past too, but to expect that the truth would never come out? That is Michael Jackson (may he RIP) level fantasy. It speaks to Oprah’s Cinderella complex: What was clearly driving her (and still is driving her and Gail) is wanting to be the white girl that even her billions will not allow her to become. To live simultaneously in that shattered faux Cinderella world and also be normal in everyday reality, no matter how many billions one has, requires deep personal awareness, long-term therapy and heavy medication, at the very least. And Oprah seems to have had none of these.

    Oprah, your slip is still showing? Go see a fortuneteller: I see more self-destructive trouble in your future. And afterwards, then please don’t walk, run to the nearest therapist. And take your girl friend Gail Bumpus along with you. Two stars

  2. Great blog post. It’s useful information.

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