Oprah (19 page)

Oprah enjoyed playing with the subject of race. “ ‘I say, Mabel, is that girl colored?’ ‘Why, ah believe she is,’ ” she would say, imitating an imagined viewer first tuning in to her show. “When I give a speech, the little old ladies say, ‘What’d she say?’ ‘She said she used to be colored?’ ” Depending on which publication she was talking to, she either emphasized or dismissed her struggle as a black woman in broadcasting. She told African American magazines she found it tough to watch white news people advance ahead of her, although none ever had. “There was another obstacle,” Oprah said, voicing her deepest insecurity. “I was too black-looking. A lot of producers and directors were looking for light skin, tiny noses, small lips. It was a heartache for me and a source of anger as well.” To white reporters she claimed she never experienced discrimination. “Even when I was growing up on a farm in Mississippi I believed I would do great things. Everybody was talking about racism, but I always believed I was as good as everybody else. It never occurred to me that I was less than all the little white kids.” She told
Cosmopolitan:
“Truth is I’ve never felt prevented from doing anything because I was either black or a woman.”

Oprah identified herself as a woman first and then as a black woman, but certainly not as a black spokeswoman. “Whenever I hear the words ‘community organization’ or ‘task force,’ I know I’m in deep trouble. People feel you have to lead a Civil Rights movement every day of your life, that you have to be a spokeswoman and represent the race. I understand what they’re talking about, but [I] don’t have to do it, don’t have to do what other people want [me] to do. Blackness is something I just am. I’m black. I’m a woman. I wear a size 10 shoe. It’s all the same to me.”

Yet she understood the commercial advantage of being a woman of color. “There aren’t a lot of black women in the Chicago media,” she said. “When I came on the air here it was like you could hear TVs clicking all over the city.” She entertained her audiences with stories about being “a little nappy-headed colored chile,” and gave them just enough shuffle and jive to feel hip. More important, though, she brought a heartwarming black presence into white suburban homes that lacked diversity. Debra DiMaio said the station manager was delighted he had managed to find someone who wasn’t an “Angela Davis type who’d picket the station with a gun in her hair.”

Oprah became the first black woman to successfully host her own daytime talk show on national television, although Della Reese had hosted a daytime variety show from 1969 to 1970. Oprah arrived at a time when African Americans were finally triumphing on the air: Bryant Gumbel reigned over the number one rated network morning program,
The Today Show,
and Bill Cosby dominated prime time with
The Cosby Show,
the country’s most watched television program. As a black female, Oprah benefited from affirmative action, but she also brought immense talent to her place at the table.

Much too shrewd to leave success to serendipity, she became the grand marshal of her own parade. She courted the Chicago media, befriended columnists, and burbled to reporters, granting every interview requested. She even gave full access to a waiter who wanted to write about her. “I had never done a one-on-one interview before I met Oprah,” said waiter-turned-writer Robert Waldron. “I first called to do a piece for
Us
magazine, and was given four days of interviews, but then the piece was killed by the owner, Jann Wenner. Alice McGee, who handled Oprah’s fan mail then, wanted me to place it elsewhere, so she helped me get the article on the cover of
The Star
[tabloid]. Oprah was delighted. Then I went back and proposed writing her biography. I nearly fainted when she said yes.” The book, titled
Oprah!,
was published in 1987.

“Oh, those were the good old days,” said Robert Feder, former television critic of the
Chicago Sun-Times.
“Oprah was a reporter’s dream then…open, accessible, genial, and extremely cooperative….I could always get her on the phone….She’d call and leave me voice messages….We’d lunch once a week in her office, where she’d pad around in bare feet or prop her cowboy boots up on her messy desk.” At the start of each television season she sat down with Feder for a Q&A session about her plans and projects. For years he kept on his office wall a framed photo of the two of them that she had signed: “Hey, what a team! Oprah.” Feder, her biggest cheerleader for a decade, removed the photo in 1994, the year many Chicago reporters call “The Dawn of the Diva.”

Upon her arrival in town, Oprah saturated the media with so many items about herself and her thighs and her eating binges and her nights without a man that by the end of 1985, Clarence Petersen of the
Chicago Tribune
pronounced her “the city’s most over-celebrated celebrity.”
Even Feder wrote, “Cool it on any more stories about Oprah Winfrey—until she wins an Oscar.” But reporters could not get enough of Oprah, who was as enthralled with herself as they were. During an interview with
The Philadelphia Inquirer Magazine
she gushed like a geyser:

The writer ended her profile by saying: “Thank you, Oprah. Now, please, hush up.”

But Oprah didn’t, couldn’t, wouldn’t hush up. Instinctively she knew that talking, talking, talking kept people from probing, probing, probing. The more she seemed to reveal about herself, the more she could hide, and still appear to be open and forthcoming. Her stories—the ones she chose to tell—were winning and farm fresh, which always left audiences rooting for her success.

“My greatest gift is my ability to talk,” she told the writer Bill Zehme, “and to be myself at all times, no matter what. I am as comfortable in front of the camera with a million people watching me as I am sitting here talking to you. I have the ability to be perfectly vulnerable at all times.”

Most of the media welcomed her self-promotion. What they may have branded as arrogant in someone else, they accepted as authentic in Oprah. She was allowed to play in the same league as baseball great Dizzy Dean, who said, “If you done it, it ain’t braggin’.” Shining her own star paid off so well that when she went national in 1986, she demanded control of her own public relations so she could continue shaping that image.

As the local host of
The Oprah Winfrey Show,
she received her first national publicity in
Newsweek,
when she dethroned Phil Donahue in the ratings. She was thrilled to get a full page in the national news magazine, but she resented being described as “nearly two hundred
pounds of Mississippi-bred black womanhood, brassy, earthy, street smart and soulful.”

“I did not like it,” she told the writer Robert Waldron. “I don’t like the term ‘street smart.’ I think it’s a term that gets put off on black people a lot. Rather than say intelligent, it’s easier to say we’re street smart and that kind of explains a lot of things. ‘Oh, well, she made it because she’s street smart.’ Well, I am the least of the street smarts. I’ve never lived on the streets. I don’t know anything about it. I never was a hustling kid. I mean, I had my days of delinquency. But I was never like a hustling kid, or streetwise. I wouldn’t last ten minutes on the streets.”

Despite her defensiveness, she admitted that the
Newsweek
article “opened a lot of doors for me,” including the ultimate in celebrity beatification: an invitation to appear on
The Tonight Show.

“They said if I appeared with [substitute host] Joan Rivers, I could come back and appear with Johnny Carson. I said, ‘Nooo problem.’ ”

The warden of the Cook County Jail was so taken with Oprah that he allowed inmates to stay up past their regular curfew to watch her that night.

Jeff Jacobs, who accompanied Oprah and her staff to LA, told her to tape a couple of shows to promote ABC’s miniseries
Hollywood Wives.
This would ingratiate her with the network that owned and operated WLS, bring a little glamour to her local audience, and promote her appearance on television’s premier late-night show. So with her camera crew in tow, Oprah lunched at Ma Maison and strolled the shops of Rodeo Drive with Angie Dickinson, Mary Crosby, and author Jackie Collins, sister of movie star Joan Collins.

The night before, she met her friend Maria Shriver and then-fiancé Arnold Schwarzenegger for dinner. “We sat in a restaurant booth and Arnold played Joan Rivers. He kept pumping me. ‘Why are you successful?’ ‘Why did you gain weight?’ ”

At the time, Joan Rivers was famous for skewering Elizabeth Taylor with fat jokes: “She’s got more chins than the Hong Kong phone book….” “Her bumper sticker says, ‘Honk if you have groceries.’ ” “The three biggest boobs in Virginia are John Warner [husband number six] and Elizabeth Taylor.” So it was inevitable that the subject of
Oprah’s weight would come up during her seven-minute appearance on
The Tonight Show.

Standing behind the curtain on January 29, 1985, Oprah listened to Joan Rivers’s introduction: “I’m so anxious to meet her. They talk about her as streetwise, brassy, and soulful. Please help me welcome—Miss Oprah Winfrey.”

Oprah felt put down. “I thought, ‘Uh oh…She’s read too much about this street-wise…Negro woman. I mean when you hear that you think I’m gonna come out with a chicken and a watermelon wearing a bandana around my head.”

Oprah walked out in a royal blue suede dress dripping with strands of sequins and split up the front to reveal white hose and an $800 pair of blue suede shoes sparkling with rhinestones. In the fashion of the day, her hair was teased and sprayed to a lacquered hardness. Her eyes were painted purple and red, and her red lips were outlined in purple to complement the dress, which she said had been custom-made in Chicago by someone named Towana. Her earrings dripped with dangling rhinestones. She looked like she had come straight from a lounge act, without time to change at the truck stop.

Joan asked about her childhood, and Oprah spun her stories of “whuppins” and “pet cockroaches” before the conversation turned to dieting.

“How did you gain weight?” said Joan.

“I ate,” said Oprah.

“You’re a pretty girl and single. Lose it.”

Oprah said later she wanted to slap the comedienne. “But…I’m on national television for the first time….Then Joan Rivers, who is this small, made a bet with me to lose weight. I said okay. I’m on national television. What else am I going to say?”

Rivers said she would lose five pounds if Oprah lost fifteen. They shook hands and agreed to meet back on the show in six weeks to see who had won.

Oprah returned to Chicago the next day and made a reservation for her “final feast” at Papa Milano. She invited her staff to join her. “They are my family,” she said. “We eat almost every meal together.” She
alerted the media to cover the revel, which Debbi DiMaio said started at 7:30
A.M.
with grilled cheese sandwiches. Then came breakfast at the Pancake House. “I ordered real pancakes, potato pancakes, and an omelet,” said Oprah. “When they brought the pancakes out, they said, ‘We made these reluctantly because we want you to win your bet with Joan. Don’t eat them all.’ Then for lunch I had my last super-duper order of French fries. So I had my favorite food—potatoes—twice.”

The dinner menu consisted of pizza, pasta e fagioli, garlic bread, sweet peppers, ravioli, salad, cannoli, cookies, and spumoni. The next day a picture appeared in the
Chicago Tribune
of Oprah feeding a slice of pizza to her then-boyfriend Randy Cook, a tall, light-skinned African American man with a mustache.

“I was Stedman before Stedman,” Cook said many years later. “I lived with Oprah in her apartment from January through May 1985.”

Their five-month affair became a torment for Oprah years later, when Cook decided to go public with their relationship and write a book. By that time Oprah was living with Stedman Graham, who ran Athletes Against Drugs. Cook’s book proposal was titled
The Wizard of O: The Truth Behind the Curtain: My Life with Oprah Winfrey.
His chapters included:

• Oprah Introduces Me to Smoking Cocaine
  
• Oprah: Drugs, Sex, Out of Control
  
• Oprah and Gayle
  

He described how Oprah introduced him to drugs and freebased her own crack cocaine in her twenty-fourth-floor condo. He wrote graphically that they became “carnally driven monsters” and indulged in “animalistic sex.” He said Oprah regularly gave him her bank card to withdraw money to buy their drugs. She was the financier; he was the supplier. He claimed he became addicted because of Oprah, and his life spiraled out of control. When he bottomed out, he lost his job, declared bankruptcy, and finally got into a twelve-step recovery program. “One of the steps requires me to make amends,” he wrote. “For me this means reaching out to Oprah. I go to her studio to talk but Oprah completely denies my existence.”

Rejected and angry, Cook decided to write a tell-all. He sent his proposal to publishers, but no one wanted to publish a book about a beloved American icon cooking up crack cocaine and smoking herself sky-high. So Cook contacted Diane Dimond, the investigative reporter for
Hard Copy,
a tabloid news television show devoted to celebrity exposés that ran in syndication for ten years.

“In my experience with
Hard Copy,
which was owned by Paramount Pictures, there wasn’t anyone we couldn’t cover,” said Diane Dimond. “I did stories on Michael Jackson and Heidi Fleiss [the Hollywood Madam, who went to prison], and she had the names of all my bosses in her little black book. I covered O. J. Simpson and I broke the William Kennedy Smith rape case, so no one seemed off-limits. But I found out fast that Oprah Winfrey was definitely the one untouchable when Linda Bell Blue, my producer…got a call from none other than Jonathan Dolgen, head of Paramount, who screamed and yelled until Linda promised to call me off….She told me that we could not be seen as attacking one of the most successful black women in America….I had talked to Cook and his lawyer several times…but at that point I had to drop the story.”