Oprah On Oprah

But a growing empire produces tough challenges. Winfrey is used to ironclad control. A shrewd businesswoman, she still signs all the checks of more than $1,000 for her Harpo Entertainment Group, and she meticulously scrutinizes the smaller ones that others sign for her. She binds employees at all levels to strict, lifelong confidentiality agreements. And she guards her off-air ventures as fiercely. For two years she barred the press from the course she taught with longtime boyfriend and sports-marketing executive Stedman Graham at Northwestern University's business school. Students who talked to reporters could face disciplinary action from the school. (NEWSWEEK was the first news organization allowed into the class.) But as Winfrey's holdings multiply, she is beginning to accept that she simply cannot micromanage them all. In November, O magazine ran a glowing profile of a Chicago center for at-risk girls, only to be embarrassed a month later by a newspaper report that the facility was under investigation for unsanitary living conditions. A magazine spokeswoman says that O was unaware of the investigation, and she has no further comment.

Far tougher than managing her fast-growing businesses is Winfrey's struggle for personal balance. While she is touching more lives than ever, she is also more removed from her fans. With a fortune estimated at $800 million and an expanding list of advisers, liaisons and handlers on her payroll, she risks losing the personal connection so crucial to her appeal. Some old fans say they're turned off by Winfrey's increasingly broad, humanistic approach to such topics as spirituality. "I wish she'd go on and say 'God' and stop talking about a higher being," says Fertina Bell, a church administrator in Los Angeles. "She can say 'Jesus.' She has enough money. If they cancel her show, she can still live." The pressures of managing it all--the talk show, the movies, the magazine, the teaching--have left Winfrey exhausted and eager to lighten her workload. "I hit my tipping point this year," she told NEWSWEEK.

This phase of Winfrey's career follows one of the most painful episodes in her life. Just mention the word "failure," and Winfrey's eyes, usually bright and laser-focused, go distant and dim. "Ahhh... 'Beloved'," she says, sighing. Her film adaptation of the complex Pulitzer Prize-winning Toni Morrison novel about a former slave haunted by the ghost of a dead child tanked at the box office when it opened in October 1998. Trounced by movies like "The Bride of Chuckie" and "Pleasantville," "Beloved," in which Winfrey also starred, never climbed higher than fifth place in ticket sales. Its domestic gross was just $23 million--less than half what it cost to make.

The stinging defeat sent Winfrey into a month long funk. For years her fans had followed her unconditionally. It never occurred to her that they wouldn't follow her to the box office, especially to embrace a project she cared so much about. Every day on her show she preached self-help, but in private she felt rejected and depressed. Never in all her public life had anything--not jokes about her weight or tabloid stories about her personal life--wounded her so deeply. At night she fell to her knees and prayed for release from her pain. "I felt like I was behind a wall," says Winfrey. "I could hear other people laughing, and I could feel that I should be happy, but I wasn't because I was so deeply saddened."

She sought solace in work. But instead of solo projects like "Beloved," Winfrey entered partnerships to ease the burden of professional and emotional risk. She teamed up with cable-industry powerhouse Geraldine Laybourne to co-found Oxygen Media, a now-faltering cable and Internet venture for women. Soon after, Good Housekeeping editor Ellen Levine called Winfrey with an idea about starting a magazine.

It wasn't the first time she'd heard the pitch. A string of publishers, spurred by the huge success of the monthly book club (which has since 1996 turned dozens of unknown books into instant best sellers), had approached the talk-show host about lending her name to a monthly. She dismissed them all. But just before Levine's call, an audience member had suggested she'd like a print version of the talk show, and Oprah, who believes in signs from God, took it as one.