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Oprah Unbound

FROM DECEMBER 2008: After 25 years, Chicago’s Media Queen builds a bigger business and charitable empire, dabbles in politics, and strikes out for the West. Can $2.7 billion buy happiness?

(page 1 of 5)


Great moments in O’S TV history

From breakthrough performer in the 1980s to Media Queen today

Giving and receiving—a sampling of honors for a worldwide star

We ask fans why they stand in line to see Oprah

Oprah Winfrey says her favorite room in her California home is the library, and that makes sense. After all, as the Queen of Media says, she wouldn’t be the person she is today if she hadn’t been able to read books while growing up in Mississippi and Tennessee. Books, she frequently notes, opened the world to her. This cozy library is in her 23,000-square-foot home in Montecito, a posh community near Santa Barbara and her primary residence when she is not in Chicago taping The Oprah Winfrey Show. The walls in the library are celadon green, the better to showcase the shelves of red leather–bound books: an eclectic but thoughtful collection that covers art, fashion, inspiration, and literary works by African American writers.

With its cream-colored sofas (on which Winfrey’s dogs are welcome) and its decorative painted tables, the house seems casual and airy, as seen on TV and in Winfrey’s home-design magazine. Yet, in a story Winfrey likes to tell, she says that she had lived in her Montecito house for five months before she wondered if there was a television set on the premises, tucked in somewhere by her interior designer. Even then, she looked for one only when her longtime companion, Stedman Graham, was heading out to a friend’s house to watch a football game. They found one set, hidden away upstairs.

The Queen of Media doesn’t know if there is a television set in her house? “I don’t watch television,” Winfrey, 54, has said for years. Evidently, she means what she says. But through the medium of television, she has built an empire comprising movie and TV production, magazine and book publishing, a satellite radio station, and, later this year, her own cable-TV network. Obviously, her business now transcends television. Her business now is Oprah. Her brand is Oprah.

This January marks the 25th anniversary of Oprah Winfrey’s debut on Chicago television. It has been a fascinating ride—or, as it would be called on The Oprah Winfrey Show, “an amazing journey.” Winfrey has transformed herself into a cultural icon. She has gotten us to form book clubs; she has encouraged us to remember our spirits and to make a mind-body connection. She has urged us to be “our authentic selves.” In 1999, Time named her one of the most important Americans of the 20th century. In 2001, Newsweek called her the Woman of the New Century. The same year, the public’s identification of Winfrey with civic leadership was so complete that New York City’s mayor, Rudolph Giuliani, asked her to host the Prayer for America gathering at Yankee Stadium 12 days after the terrorist attacks. In 2003, she became the first African American female billionaire, and in 2007 she overtook Meg Whitman, the former chief executive officer of eBay, as the richest self-made woman in America. Winfrey is now worth $2.7 billion.

We have had 25 years together—that’s longer than many marriages. Winfrey has changed, and so have we. This anniversary is a good occasion to assess the Age of Oprah: how she started in Chicago and how she has moved away from the city; how she found the promised land; how she became political and the ramifications of her endorsement of Barack Obama for president; and how she plans to extend her brand in the future. (Winfrey declined to be interviewed for this story.) With some repercussions from her political endorsement and the realities of an aging audience, Winfrey is confronting a pivotal and complicated time. But a T-shirt sold in Winfrey’s store, across the street from her Harpo Studios headquarters in Chicago’s West Loop, might hold a key to the future. It reads, Become More of Yourself. And that is what Oprah Winfrey has always done.

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Photograph: Jason Merritt-Film Magic/Staff/Getty Images



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