Four days later, Winfrey is in perfectionist mode. Looking back at the December issue of her new magazine, O, she holds up the cover and winces. “Ooh, there’s a mistake!” she says, pointing to the word “generosity,” which she thinks should have been in bigger type. Annoyed with herself for not spotting it sooner, she grabs a stack of past issues and starts flipping. “Didn’t like that.” Flip. “Nope. Never got that right.” Flip. Flip. Realizing that she’s obsessing, she blows out a whoosh of breath and refocuses her energy on pages she likes. After several satisfied nods, she returns to the December issue and declares: “I love everything in this!” Then she turns a page, spots another imperceptible glitch and adds sheepishly: “Except this. We should have moved this.”
Hours later, while teaching a business-school class at Northwestern University, Winfrey turns on her down-home charm. The course is called “The Dynamics of Leadership,” and the night’s topic–adapting strategies of the civil-rights movement to modern business–is heavy. But Winfrey knows how to keep the three-hour class moving. When guest speaker Coretta Scott King talks earnestly of her late husband’s belief in service as the key to leadership, Winfrey raises her hand, stands and asks, “I mean, on your first date was [the Reverend King] just sitting up talking to you about service?” Laughter ripples through the classroom.
Down-to-earth diva. Control freak. Silly best girlfriend–Oprah Winfrey can be all three. From her dirt-poor beginnings in rural Mississippi to her iconic status as the “queen of talk,” the 46-year-old star has come a long way. Now, after one of the most challenging and exhilarating phases in her long career, she is peaking professionally, spiritually and emotionally. She is a multimedia tycoon, producing film and TV projects, giving away millions to charity and, most recently, putting her stamp on the world of print with a new magazine. Her journey continues to inspire women to listen to their own voices and try to play by their own rules. For the millions of women who read her magazine, watch her show and buy the books she recommends, this is the age of Oprah–and a NEWSWEEK look at her life today suggests that the woman at the center of the empire is herself at a crossroads.
If there was ever any doubt about Winfrey’s instinctive knack for taking the nation’s pulse, her new magazine should take care of that. Her monthly, O: The Oprah Magazine, launched last April, is the most successful magazine start-up in history. After just seven issues (it started as a bimonthly), O has a circulation of 2 million, beating top sellers like Vogue, In Style and Vanity Fair. Without a single guide to thin thighs or a saucier sex life, O is a glossy rendering of Winfrey’s on-air motivational crusade, encouraging readers to revamp their souls the way Martha Stewart helps them revamp their kitchens. With articles on topics like women who rush too much, soul-searching interviews with celebrities like Sidney Poitier and flourishes like pull-out quotes from the likes of Winston Churchill and Deepak Chopra, O is reeling in a whole new breed of Oprah devotees: professionals with little time to watch her show. And with 150 ad pages per issue (stellar for even the hottest mags), it has Madison Avenue types paying new attention to the woman who used to cry with dysfunctional families on TV.
Winfrey’s new magazine marks the next step in her own, personal journey. She has always made private pain–from childhood sexual abuse to a now-epic struggle with her weight–part of her public persona. With her TV show in the 1980s, she tapped into people’s obsessions with themselves and made them feel it was OK to unearth their personal tragedies. By sharing her own setbacks, like her confidence-busting weight gain after a drastic liquid diet in 1988, she also signaled that it was all right to fail. As she grew more powerful in the 1990s, her quest on-air and in private grew more spiritual–and again kept pace with the times. In an era of excess, she fed people’s desire to find meaning in life. While rivals like Jerry Springer brought families to blows, Winfrey switched direction and tried to help people take charge of their lives. As she did, her audience grew, attracting even some male viewers desperate for hints on how to manage their hectic lives. “It’s amazing how you get sucked in,” says Philip Madden, 37, a Wall Street equities salesman who watches reruns and tapes of the talk show with his “Oprah”-addicted wife.
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.
Levine and Hearst Magazines president Cathleen Black went into overdrive preparing a prototype. In January 1999 they flew to Chicago armed with three sample tables of contents, a book of page layouts and a self-shot video of women on the street professing their desire for an “Oprah” they could hold in their hands and keep. “We knew we had to engage her in a mission, not just a magazine,” says Black. They even had a name for the new product: Oprah’s Spirit.
Winfrey hated it. The word “spirit” was too loaded. The previous year the press trashed her when she started a daily segment called “Remembering Your Spirit.” The touchy-feely vignettes, preproduced with soft light and new-age music, were testimonials from people around the country who had, usually as a result of crisis like the death of a child or a divorce, stumbled onto some simple truth about life. They were part of a larger new feature on her show called “Change Your Life TV.” Confused viewers complained that the talk-show host was meddling with their religious beliefs. Critics wrote articles about “the church of Oprah.” Hurt by the criticism, Winfrey dropped the “Change Your Life” mantra and toned down the “Spirit” segments with (slightly) lighter tag lines like “Remembering Your Joy.” A magazine called Oprah’s Spirit, she feared, would dredge up old controversy.
Laughing now about her near pass on the magazine, Winfrey runs over to her desk and snatches up a reminder of another project she almost rejected. Encased in a small black frame, it is an August 1996 inter-office memo from one of Winfrey’s producers. “Each month Oprah and some viewers could get together and decide to read a novel or a book of Oprah’s choice,” the pitch reads. Initially Winfrey thought the book segment would be too boring for TV. But when she realized it would give her a chance to meet some of her favorite authors, she decided, reluctantly, to give it a try.
Like the book club, the magazine was a huge hit. Soon after the first million copies hit stands in April, the phone lines at Harpo’s studios were buzzing with calls from fans complaining that their grocery stores and corner news vendors were sold out. Hearst rushed to print an additional 500,000 magazines, and soon those, too, were gone. Barnes & Noble alone sold a record 100,000 copies. The only single edition of a magazine to sell even close to that amount for the book chain was the 1997 Sports Illustrated swimsuit edition with Elle MacPherson on the cover (and that sold a distant 81,000 copies).
The public was going wild, but inside the magazine’s New York offices tensions were running high. Winfrey seemed out to break all the rules. She demanded that O’s table of contents be on page two–unheard of at women’s mags, which reserve the first dozen or so pages for top advertisers. When she got word that Hearst was planning to coposition the first issue with Cosmopolitan on special display stands, Winfrey called the publishers and huffed: “I am not going to be used to sell one of your other magazines. Cosmo is not who I am.”
Now the first issue was flying off the stands, and she still wasn’t satisfied. The layouts weren’t lush enough, the writing wasn’t smart enough. She ordered numerous reshoots and story revisions as they prepared the second issue. Adding to the stress, Winfrey’s chief liaison at the magazine was her best friend, Gayle King, a television anchorwoman with no print experience, whom Winfrey installed in the powerful position of editor at large, second in charge to the editor in chief. Initially it was Hearst’s idea for Oprah to appoint a personal liaison to smooth communication with the Chicago-based star. “None of us were ever under the illusion that I was hired for my magazine expertise,” says King, who has known Winfrey since they worked together at a Baltimore TV station in the 1970s. “I was hired because I know what Oprah likes and because I can get her on the phone.” But in the high-pressure environment, it added another confusing rung to the hierarchy.
The pressure became too much, and by the third issue a handful of top staff, including editor in chief Ellen Kunes, resigned. “It was like riding a rocket, and the only one who was prepared for it was Oprah because she’s been riding it for years,” says Kunes, 41, who left, she says, to spend more time with her children.
The magazine’s growing pains have not stunted its growth. Winfrey found a new editor in Amy Gross, a tough-minded magazine veteran who, like Winfrey, is a perfectionist. (The early issues were “too earnest and full of trite and cliche magazinespeak,” she told Winfrey and King at her first interview.) She’s overhauled the writing and design staff to make the magazine more sophisticated, she formed an instantly close relationship with King, and so far she seems unthreatened by Winfrey’s involvement. “It’s my ship, but Oprah’s the North Star,” she says of her approach to the job.
Fans say they like the magazine for the same reason they like the TV show: it’s real. Winfrey has graced every cover so far, and, unlike most cover girls, she represents an attainable standard of beauty. “It’s not just perfect, tall, blond models,” says Terrie Reeves, 37, a marketing consultant. The November issue features Oprah in a fire-red taffeta Gianfranco Ferre gown. The day it was released, Ferre was flooded with orders from women around the country, including an opera singer in Conyers, Ga., who e-mailed her request for a size 18 and a New Yorker who rushed into the Madison Avenue boutique waving the magazine and pleading, “I must have this dress!”
Winfrey’s followers know that the life of the multimillionaire in the couture gowns is nothing like theirs. Yet they believe that her inner goals and aspirations mirror their own. “She’s giving me the tools to find myself,” says Mary Madden, 37, a suburban housewife from West Islip, N.Y. “I’m not there yet. But she gives me the inspiration and the courage to take the journey.” Madden, who has three young sons, watches the talk show religiously, and frequently logs on to Oprah.com. She buys Oprah-recommended books, has a subscription to O magazine and writes every day in her “gratitude journal” (one of Oprah’s favorite exercises for acknowledging the goodness in life).
Ever restless, Winfrey is constantly working to get her message out. That’s why she took on the teaching job at Northwestern. Yet another manifestation of her spiritual mission. the class was for her a way to groom a new crop of business leaders committed to developing purposeful and fulfilling careers. But the demands of teaching have taken their toll. The morning after the class with Coretta Scott King, Winfrey, clearly exhausted, shuffles through her Chicago penthouse in her favorite cream-colored pashmina pajamas. The class didn’t end until 9 p.m. And prior to teaching, she had sprinted through a jam-packed day: early morning workout, 8 a.m. makeup call, talk-show taping, off-air chat with audience members, postproduction meeting with producers, afternoon review of O layouts and telephone volley with her lawyer to discuss buying a new building–all before slurping down a bowl of chicken-potato soup, rushing to meet Stedman, picking up their cocker spaniel, Sophie, from the vet and hustling to the suburban campus for the 6 o’clock lecture. Now Winfrey has a pile of case studies and personal journals to grade. “The magazine, the grading, I haven’t managed it all as well as I should have,” she says, clutching a cup of coffee. After several nights of lost sleep she has decided to give up the class.
Relaxing in a small sitting area and library designed around a large antique oil portrait of an angelic-looking black girl, Winfrey, though tired, looks peaceful. Through the trials of the past few years she has learned some important lessons about herself. “I’m a communicator, a catalyst through which information flows,” she says. “But I don’t have to do it all on my own.”
With that realization Winfrey is now finding ways to strike a balance. She’s extended the syndication contract on her talk show until 2004. But she’s ushered in a stable of regular on-air experts to lighten her on-air responsibilities. She has also reduced her role in Oxygen Media, which stumbled out of the gate after it was launched last year. Though flush with funding, it is struggling for distribution and recently cut programs and laid off employees. She is giving up classroom teaching, but she’s reworking her leadership curriculum for use on the Internet, a solution that frees her from the drudgery of grading. And while she still sees room for much improvement at O, the easing of creative tensions has allowed her to enjoy the buzz about the magazine.
Before hitting the treadmill and jumping into her day, Winfrey pulls out a piece of personal stationery inscribed with one of her favorite quotations. It’s from 19th-century transcendentalist Ralph Waldo Emerson: “What lies behind us and what lies before us are tiny matters compared to what lies within us.” And with just the faintest hint of a smile, she signals that there is a lot more of Oprah yet to come.
