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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.

* * *

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

 

 

 


In early 2007, at the opening of the school Winfrey founded in South Africa

 

CHICAGO: HER PART-TIME KIND OF TOWN

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When Winfrey started as the host of A.M. Chicago in January 1984, the half-hour program was considered a throwaway slot. It ran at 9 a.m. against The Phil Donahue Show, and Donahue, also based in Chicago, was dubbed “the titan” of daytime talk. With her close-cropped hair and bubbly enthusiasm, Winfrey modeled her show after Donahue’s—setting up on-air debates (Should this woman stay with this cheating man? Should children be spanked? Is it wrong to be a cross-dresser?). But while Donahue’s persona was cerebral, Winfrey came across as the gal next door, an image underscored by the frequent sightings of Winfrey riding the bus to the WLS-TV studio in the Loop. Within three months, she was beating Donahue in the Chicago market. By 1985, A.M. Chicago had been renamed The Oprah Winfrey Show and had been expanded to an hour. The following year, it went into national syndication, and Winfrey captured two daytime Emmys.

In the beginning, she would pad around the green room at the TV station in her stocking feet; backstage she would hover around the edge of conversations that celebrities—Jeremy Irons, Mel Gibson—were having, starstruck and tentative. “She was the kind of person who would go get her own soda and ask you if she could get you one, too,” recalls an early visitor. Over time, her hair got big (for a while bouffant), and her impact got bigger. As Fortune magazine wrote, “Oprah’s life is the essence of her brand.”

And that life was openly intertwined with Chicago. Winfrey ate at the modest Papa Milano’s on State Street. In 1989, with the Lettuce Entertain You mogul Rich Melman, she opened a restaurant, The Eccentric, and would often pop in to say hello to customers or to eat some of “Oprah’s mashed potatoes,” a popular menu item. She started dating Stedman Graham, the chief executive officer of his own marketing, management, and consulting firm and the former boyfriend of the local television news anchor Robin Robinson. By 1992, Winfrey and Graham were engaged and talking about wedding dates. In her quest for fitness, she could be seen running along the lakefront in the early morning or working out at the East Bank Club. Even when she wanted some free time, she didn’t go far. Weekends were spent outside La Porte, Indiana, on her 164-acre estate anchored by a French farmhouse. The property was equipped with a ten-stall horse barn, a helicopter pad, and roaming llamas. In the summer, Winfrey ran on back roads and waved to neighbors.

But slowly, her focus changed. That started with her television show. “It’s time to move on from ‘we are dysfunctional’ to ‘what are we going to do about it?’” Winfrey told The Boston Herald in 1994. Her show changed directions, emphasizing the positive, healing, and self-fulfillment. “Her rise mirrors the dramatic growth of therapy as an institution in American culture,” says Janice Peck, an associate professor in the school of journalism and mass communications at the University of Colorado and the author of The Age of Oprah: Cultural Icon for the Neoliberal Era (Paradigm Publishers, 2008), a book about Winfrey’s widespread influence. “The forms of spirituality she has embraced and the emphasis on personal responsibility—these can be seen as an element of American history. Oprah does reflect her times.”

That change moved Winfrey’s show away from what was then a proliferation of trashy TV talk shows (with hosts such as Jenny Jones, Jerry Springer, and Ricki Lake), and when the scandal of a former Jenny Jones guest murdering another guest exploded in 1995, Winfrey was already far above the fray. In 1996, she started her book club, which played a seminal role in elevating Winfrey to iconic status. Most of her choices became instant bestsellers. Two years later, she introduced an occasional segment on her show, Change Your Life TV. She performed the theme song herself and conferred with self-help gurus such as the psychologist Dr. Phil McGraw, the financial adviser Suze Orman, the relationship mentor John Gray, and the spiritual writer Gary Zukav. Remembering Your Spirit, a five-minute segment about finding one’s center, ended each episode. Journaling and the search for “new truths” were encouraged, but for the first time, Winfrey’s ratings dropped. Two months later, she dialed back Change Your Life TV, cutting those themed shows by almost a third.

Winfrey’s own center seemed to change, too. She wasn’t seen riding the bus anymore. In 1995, she and Melman shut down The Eccentric. The relationship with Graham continued, but a wedding never materialized. In 1998, Winfrey told this reporter: “I see no reason to get married if I’m not going to have children. And I’m not. I could not do what I do as well as I’m doing it and have a child. Impossible.” Winfrey’s time in Chicago now centers on the shooting schedule for her show: She flies in from California on Monday night; works at Harpo on Tuesday, Wednesday, and Thursday; and then flies out Thursday evening.

The visitor who remembers Winfrey from the old days, asking people backstage if she could get them a soda, met with her again a few years ago. “Things had changed,” he recalls. “I don’t think the queen of England is treated with such deference and formality.”

In Chicago, Winfrey is protected and hidden from random view. Since 1984, she has lived in Water Tower Place, in what is now a 15,000-square-foot duplex. Some residents in the building say they rarely see her on the elevators. Recently, she bought a 5,000-square-foot co-op on East Lake Shore Drive, one of the most exclusive addresses in the city. But she abandoned the idea of downsizing her Chicago duplex and moving there when she realized that residents from nearby apartments could see into her windows. That apartment has been sold.

When she isn’t here, Winfrey is spending time at her Montecito retreat—“We know she is here when we see her jet,” says a neighbor—or at her 102-acre home in Maui. She is visiting the Oprah Winfrey Leadership Academy for Girls that she started in South Africa in 2007 or touring Italy with a group of close friends that includes the writer and director Tyler Perry and her longtime pal Gayle King, an editor-at-large for O, The Oprah Magazine. The air around Winfrey now is rarefied; her private life has a profile so low that only big money can sustain it—in her case, that profile remains very low.

Photograph: AP Photo/Denis Farrell

 

 

PROMISED LAND

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In the summer of 2001, Winfrey bought a 42-acre private estate in Montecito. Although the property was still undergoing a three-year renovation, including the building of a 23,000-square-foot Georgian-style main house, she fell in love with it. The owners, Marlene and Robert Veloz (he is a Southern California industrialist; she, a philanthropist), who had been living in the 2,000-square-foot stone gatehouse until the main house was completed, agreed to sell it to her. The price was $50 million—according to The Los Angeles Times, one of the highest prices ever paid for a private residence in the United States.

The purchase of the Montecito property marked a turning point for Winfrey—it was a move appropriate for an established cultural icon. She would eventually play up the Martha Stewart similarity by printing photo spreads of the Montecito house in her shelter magazine, O at Home, which appeared in 2004 and is published quarterly. Like all landed gentry, Winfrey named her estate—she called it Promised Land.

Montecito (meaning “little woods”) is an exclusive unincorporated area outside Santa Barbara with a quaint storybook village. In 2007, Forbes ranked the area’s Zip Code the seventh most expensive in the country. And the estates of Montecito—with their views of both the ocean and the mountains—are highly prized. The property that Winfrey bought was originally developed in 1934 by a scion of the Libbey Owens Ford glass company. “It was a lovely old Montecito estate, with a lake and several ponds,” says J’Amy Brown, a local writer and the past president of the Montecito Association, a homeowners’ group dedicated to protecting the semirural character of the community. In 1998, the Velozes bought the property for $14 million and began renovations, starting with the construction of the stone gatehouse.

When Winfrey bought the property, she continued the renovations, making adjustments to suit her style. (The Velozes moved to a four-acre estate that had once belonged to Arianna Huffington and her former husband, Michael.) Winfrey’s fitness guru, Bob Greene, was named the property manager, and his cell-phone number was distributed to Winfrey’s Montecito neighbors. “If there was a problem with anything during construction, it was taken care of immediately,” says Brown. Dump trucks and concrete mixers were parked ten miles away, and when needed, they were called to the site by radio phone. “Around the same time, several other newcomers moved into the area, including the Chicago Beanie Baby mogul Ty Warner,” says Brown. “So we’ve seen some new things here, like security cameras pointed out to the road.”

After a year of renovations, Winfrey’s house was finished. Inside, it projects a genteel English air, with floral fabrics, upholstered chairs, and vases of full-blown roses. The acreage across the street from the house has been transformed into a meadow.

Montecito insiders say that Marlene Veloz shepherded Winfrey around her new hometown and introduced her to many of the people she socializes with today: Jelinda and Barry DeVorzon (she is the past president of the local film festival; he is a songwriter) and Margo and Jeffrey Barbakow (she is a philanthropist; he, the former chief executive officer of the Tenent Healthcare Corporation). Residents would often spot Winfrey in the village popping into stores and Trattoria Mollie. Another new presence in town: Stedman Graham, who had moved into the estate with Winfrey. “I often see Stedman more than Oprah,” says Mindy Densen, a Montecito neighbor. Evidently, warmer climates agree with Winfrey; in 2002, she purchased 102 acres in Maui for $8 million and hired the New York interior decorator Elissa Cullman to create an American farmhouse on the waterfront. (In 2006, Winfrey’s plans to add 63 acres of adjacent land fell through.) At the same time, she put her 85-acre ranch in Telluride, Colorado, and her 164-acre retreat in La Porte, Indiana, on the market, and both properties were later sold.

* * *

 


Winfrey salutes candidate Barack Obama after a 2007 rally in New Hampshire.

 

POLITICS

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From the beginning of her television show in Chicago, Winfrey had refrained from making any political endorsements. She was above politics, she said. Even in 1996, when the Democratic Party held its national convention at Chicago’s United Center, only blocks from Winfrey’s Harpo Studios, she did not invite any politicians to appear on her show. Only John F. Kennedy Jr., who had never run for office, visited the show during the convention, and that was to promote his magazine, George.

In 2000, Winfrey departed from her own tradition and had both major-party presidential candidates, Al Gore and George W. Bush, on separate episodes of her show. Still, she did not endorse either candidate. That changed on May 1, 2007, when Winfrey appeared on the CNN show Larry King Live and announced that she was supporting the Illinois senator Barack Obama for president. “I haven’t [endorsed anyone] in the past because . . . I didn’t know anyone else well enough to say, ‘I believe in this person,’” Winfrey explained. She had met Obama and his wife, Michelle, in Chicago before his 2004 U.S. Senate bid. In 2005, the Obamas attended Winfrey’s Legends Ball, a white-tie affair celebrating African American women, at her Montecito home. In September of that year, says a friend of Michelle Obama, Winfrey and Barack shared a flight to Houston, where they checked in on Hurricane Katrina refugees. On the plane, the two bonded over their unusual “O” names, sharing people’s past suggestions—Joe O’Bama and Suzie Winfrey—for mainstreaming their names.

Winfrey’s endorsement was not entirely surprising. At her Legends Ball, she had jokingly suggested to Obama that her estate would be a great place for a fundraiser. And in October 2006, when both the Obamas appeared on her show, Winfrey publicly urged Barack to run for president, saying that if he did declare his candidacy, she would support him.

In an effort to draw a line between her show and her private opinion, Winfrey gave her endorsement on King’s show, rather than on her own. “My value to [Obama]—my support of him—is probably worth more than any other check I could write,” she said then. Although historically there is little evidence that celebrity endorsements draw voters to a candidate, Winfrey’s television show had produced some effect in a past election. On September 19, 2000, George W. Bush appeared on Winfrey’s show and talked about his decision to stop drinking and his love for his daughters. At the time, Bush trailed Al Gore by five points in a CNN-USA Today poll. The following week, the same poll showed Bush tied with Gore. Some news reports called it “the Oprah bounce.”

But for the 2008 election, Winfrey was not inviting the Obamas, or any other declared candidate, on her show. In an audio chat on her Web site in August 2007, Winfrey said it would be “disingenuous of me to be sitting up there interviewing other people . . . pretending to be objective.” Late in 2007, Winfrey hit the campaign trail with the Obamas, appearing at rallies in Iowa, New Hampshire, South Carolina, and California. The South Carolina rally had to be moved to a football stadium to accommodate the crowd of 29,000. Through Winfrey’s appearances alone, the Obama campaign estimated it garnered 10,000 new volunteers. The Washington Post wrote that most celebrity endorsements don’t matter, “but this one might.” And a study by the University of Maryland professors Craig Garthwaite and Timothy Moore concluded that Winfrey’s endorsement had resulted in a million votes for Obama in the primaries and caucuses.

Winfrey appeared to pay a price. According to a Gallup poll conducted in October 2007, shortly after her endorsement, her favorable rating fell by eight points, from 74 percent in January 2007 to 66 percent. Meanwhile, her unfavorable ranking rose by more than half, from 17 percent to 26 percent. It is unclear whether that trend will continue, but as Fortune once pointed out, if people decide not to trust Oprah, the person, the brand could quickly fizzle.

“With the Obama endorsement, I do think her image has been very politicized,” says Janice Peck, the author of The Age of Oprah. “On message boards for Oprah’s Web site, it used to just be adoring fans.

After the endorsement, you began to see some very negative responses. Now, it could be that these people are not her normal fans in the first place. But I do believe that her endorsement has caused some ripples among her fans.”

Part of the problem, Peck says, is that Winfrey has always presented herself as being above politics. “Then, suddenly, she got down into the muck of politics. So there are fans who are angry she endorsed anyone at all, Republicans who are angry she endorsed a Democrat, and Hillary Clinton supporters who are angry she didn’t endorse Hillary. Now, on her own Web site, I have started to see claims that she is a racist—that some fans feel she has endorsed Obama only because he is black. It’s incredible that she would see postings on her Web site accusing her of racism.”

On September 8, 2007, Winfrey hosted a spectacular fundraising party for Obama at Promised Land. More than 1,600 guests attended, with the ticket price starting at $2,300. Inside the gates, guests could mingle on the lawn, eat mini burgers and corn on the cob, and listen to a concert by Stevie Wonder. George Lucas was spotted; so was Sidney Poitier. Obama’s Chicago confidants Valerie Jarrett and John Rogers were present. No press was allowed, and most guests had to park in a lot eight miles away and be bused to the estate. On the Thursday before the event, signs were posted around Winfrey’s neighborhood, saying that the roads would be closed that Saturday.

“You are supposed to send a letter to the neighbors, not just post a sign,” says the Montecito resident J’Amy Brown, who admits that she was peeved about the lack of permits. After being invited and paying her $2,300, Brown was then disinvited, and her money was returned. Apparently the column she had written for the Santa Barbara Independent the week before, saying that she would be attending the party, was enough to get her nixed by Obama’s staff.

By 3 p.m. the day of the party, the Montecito roads were in gridlock. “We don’t have streets,” says Mindy Densen, who lives down the block from Winfrey. “We have tiny lanes. With all the buses, some of us worried about the safety of our kids and our dogs.” Still, Densen says, the Obama party was not an inconvenience for the neighborhood. She and her husband still held the annual block party that had been scheduled for the same day—although they did add cardboard cutouts of Obama and Winfrey “so all of us could feel we were part of the hoopla, too.” That starry night raised $3 million for Obama’s campaign.

On August 25th, Winfrey attended the Democratic National Convention in Denver. She kept a low profile during the week. After Obama’s acceptance speech, Winfrey told the reporters that she had “cried [her] eyelashes off” listening to the speech. Then on September 5th, just after the Republican convention ended, the Drudge Report, a conservative Internet site that covers politics, entertainment, and current events, posted a report that a disagreement was dividing the staff for Winfrey’s show. According to Drudge, half the producers were urging Winfrey to invite Sarah Palin, the governor of Alaska and the Republican vice-presidential candidate, to be a guest on the show but that Winfrey was refusing because of her support for Obama. The same day, Winfrey issued a denial. “The item in today’s Drudge Report is categorically untrue,” she wrote. “At the beginning of the Presidential campaign, when I decided that I was going to take my first public stance in support of a candidate, I made the decision not to use my show as a platform for any of the candidates.” Winfrey denied that there had been any discussion among her producers about inviting Palin.

Again, the message boards at Internet sites were filled with scornful posts about Winfrey, calling her unfair and racist. In an effort to force Winfrey to invite Palin, some started a petition; others cited equal-time obligations. But Winfrey, a political novice, had played her cards well. The Federal Communications Commission’s rules about equal time for candidates do not apply to news programs, interview shows, or documentaries in which the candidate is not the sole focus, so Winfrey was never obligated to give equal time to anyone.

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Photograph: AP Photo/Elise Amendola

 

 


Launching her satellite radio channel in 2006

 

THE BRAND

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Her message is simple: “You are responsible for your own life.” According to Fortune, this is as consistent a selling proposition for Winfrey “as McDonald’s convenience or Wal-Mart’s ‘everyday low prices.’” The business empire that Winfrey has built for herself follows that same message: Over the years, she has formed alliances only when necessary—which means she has made very few.

The first was with the Chicago entertainment attorney Jeffrey Jacobs, who recalled Winfrey walking into his office once wearing an A.M. Chicago T-shirt and flip-flops, asking if he could set up a syndication deal for her. In 1986, they formed Harpo Productions (“Oprah” spelled backward), and Winfrey gave Jacobs 5 percent of the company. Three years later, Jacobs became the chief executive officer of Harpo and was given another 5 percent. Other alliances were made with the TV syndication company King World to distribute her shows (1986); the ABC network to air Oprah Winfrey Presents, her made-for-television movies (1997); Hearst to publish O, The Oprah Magazine (2000); and XM Satellite for the Oprah and Friends radio channel (2006).

The core of the business is clearly the television show, what Winfrey’s longtime companion Stedman Graham once called her “power base.” It airs in more than 130 countries (including a popularity in Saudi Arabia), and it produces the most revenue. Also, The Oprah Winfrey Show drives the audience for her other endeavors: television movies, magazines, Web site, and spinoff publications such as cookbooks and a DVD collection of her greatest shows. Unlike that other empire builder, Martha Stewart, Winfrey has always refused offers to take her company public. Owning herself, she believes, is to be herself.

But things have not always gone smoothly in the empire. In September 1994, Winfrey’s longtime publicist Colleen Raleigh left Harpo Productions, and two months later, she filed a lawsuit seeking $200,000 in back pay and severance. In a press release, Raleigh spoke of the “dishonesty and chaos” prevalent at Harpo; she also indicated that she felt trapped in a power struggle between Winfrey and Jacobs. Raleigh’s suit was settled out of court for an undisclosed amount, and by the time Fortune wrote a profile of Winfrey and Harpo Productions, all seemed well between the star and her chief executive officer. But soon after, Jacobs quietly left Harpo. According to some sources, a rift had started when Winfrey stopped using Jacobs’s wife as her fashion assistant; by 2002, when Jacobs was in the middle of a divorce, Winfrey felt it was time to move on. She picked Tim Bennett, a former ABC executive, to become president of Harpo Productions.

In May 2008, The New York Times suggested that the Queen of Media’s crown was becoming slightly tarnished—an accusation that Bennett vigorously disputed, noting that Winfrey’s audience remains a third larger than that of her closest competitor, Dr. Phil—starring Phil McGraw, who was introduced to the world of television by Winfrey in 1998.

Still, Winfrey’s daytime audience has dropped from a peak of nearly 9 million viewers in 2004-2005 to 7.3 million now. Her winter 2008 ABC prime-time reality series, The Big Give—in which contestants race to see who can give away the most money creatively each week—started out with high ratings, but they declined every week. ABC announced that The Big Give was set for a slot in its fall schedule this year, but Winfrey withdrew the show. The circulation of O, The Oprah Magazine is down slightly from its 2004 high of 2.7 million; the publication faces the future with a new editor, Susan Reed, after the eight-year reign of Amy Gross. One possibility for the drops, besides Winfrey’s endorsement of Obama, could lie with her recent book-club pick of A New Earth, by Eckhart Tolle. Embracing New Age spirituality, A New Earth had incurred the wrath of some Christian fundamentalists.

“She is seeming to endorse a kind of spirituality that can be offensive to traditional Christians,” says Peck. “And, again, we’re seeing a reaction against her about this on her Web site. But you have to remember, it is the Web—so we don’t really know if these people writing negative e-mails are Oprah’s long-standing fans or an angry group targeting her.” Some possible future concerns, according to Peck, include the idea “that perhaps the brand of Oprah isn’t as new and exciting anymore. And also, her audience—female, white, and college-educated baby boomers—is getting older. So it may not be anything personal about Oprah; it may just be that these people are watching less television. Or maybe there isn’t an infinite life even for a celebrity like Oprah Winfrey.”

“No, the power of Oprah is still full force,” says Bill Zwecker, an entertainment writer for the Chicago Sun-Times. One industry insider points out that while The Ellen DeGeneres Show is gaining viewers, Winfrey’s show regularly outdraws DeGeneres’s when the two go head-to-head. Winfrey’s 2008 show with “the pregnant man,” a female-to-male transsexual who was carrying a child, drew an audience a third larger than the season average. Yet Winfrey’s involvement in her radio channel has been minimal—her on-air presence is required for only 30 minutes a week for 39 weeks a year. And her radio contract expires in 2009, leaving her an easy way to exit the medium if she so desires. The biggest project on her horizon is the start-up of OWN: the Oprah Winfrey

Network, a cable-television channel being created jointly with Discovery Communications. A press release from Harpo Productions explains that the channel will be “designed to entertain, inform and inspire people to live their best lives.” Among the players will be Winfrey’s gal pal Gayle King and the Chicago interior designer Nate Berkus. OWN is expected to begin broadcasting by the end of 2009. The Oprah Winfrey Show will remain on ABC.

* * *            

“Love is in the details,” Winfrey is fond of saying. And a good example of that is The Oprah Store. The 5,500-square-foot boutique, situated across the street from Harpo Studios in the West Loop, opened in February 2008, and most of the proceeds go to Winfrey’s charitable foundation, the Angel Network. The store contains 900 of Winfrey’s “favorite things,” from baby onesies with the “O” logo to silk-covered journals for recording your passions. There are tea sets for two, workout clothes, and pajamas; in a corner called “Oprah’s Closet,” Winfrey’s discarded designer clothes (typically ranging in size from 10 to 12, and shoes in size 10) are sold. This is the perfect place to pick up a used Prada skirt ($400) or Ferre boots ($300) once owned by Oprah, a chance to walk in her shoes. Judging by the sayings on the inspirational “O” T-shirts, there is a chance to read her mind, too. LOVE WHAT YOU’VE GOT, says one shirt. Another: WHAT YOU DO TODAY CREATES EVERY TOMORROW. These are some of her guiding lines, and knowing them, following them, and selling them is part of her authentic self. This is her realm.

Photograph: Larry Busacca/Wireimage/Getty Images