by Kitty Kelley
Williams looked so chastened that one old-fashioned Catholic watching the show wondered half-humorously if Oprah was going to give him absolution: “For your penance say five Our Fathers and five Hail Marys. Now make a good Act of Contrition and go in peace.”
Like the village vicar, she tended her flock, helping them atone for past sins. She mediated the public apology of heavyweight champion Mike Tyson when he said he wanted to make amends to Evander Holyfield for biting off a piece of his ear during their 1997 title bout. Twelve years later the two men came together on her show and shook hands, hoping their reconciliation might set an example to warring gangs of young men. Although many viewers criticized Oprah for having Tyson, a convicted rapist, on her show, others saluted her. The two Tyson shows, not incidentally, garnered huge ratings at a time when her ratings were slipping.
Oprah continued to be unbending in her condemnation of child abusers, knowing all too well the trauma to victims. Interviewing a man in prison for sexual molestation, she referred to him as “slime.” Still, her contradictions could be confounding. While she gave her friend Arnold Schwarzenegger a pass on sexual harassment, she condemned rappers because their lyrics debased women. She was unforgiving of racism but pardoned the president of Hermès after his Paris store barred her entry because of alleged “problems with North Africans.” Yet she was barely civil to Hazel Bryan Massery, who as a young white student had yelled at Elizabeth Eckford, one of the Little Rock Nine, who integrated Central High School in 1957 after President Eisenhower sent federal troops into Arkansas. In the intervening years, Massery had apologized to Eckford for her hateful rants, and the two became close. Oprah invited both women on her show but was highly skeptical of their friendship and would not accept that Hazel’s remorse had led to reconciliation. “They are friends,” Oprah told her audience in disbelief. “They…are…friends,” she repeated with obvious distaste. She then showed a massive blowup of the photograph taken that historic day, showing Elizabeth, silent and dignified, carrying her books into school as a crowd of screaming white students taunted her, the most menacing being Hazel. Oprah was icy as she asked Eckford why that photo still upset her so many years later.
“She [Oprah] was as cold as she could be,” Eckford told David Margolick of Vanity Fair. “She went out of her way to be hateful.”
Margolick, who spent time with Eckford and Massery to write their story, added, “Characteristically, though, Elizabeth felt sorrier for Hazel. She was treated even more brusquely [by Oprah].”
Still, people flocked to the Church of Oprah. Online there were twenty-eight thousand websites devoted to getting on The Oprah Winfrey Show, and late-night television’s David Letterman, who had been excommunicated for years, began an “Oprah Log,” begging to be invited. Oprah ignored him, but he persisted. “It ain’t Oprah til it’s Oprah,” he told his audiences night after night. Soon his fans began holding up signs in front of the Ed Sullivan Theater, in airports, and at football games: “Oprah, Please Call Dave.”
After eighty-two nights, Phil Rosenthal advised Oprah in the Chicago Sun-Times, “This is a call you have to make….Every night…he is making you look like a humorless, self-important diva who spouts all kinds of New Age platitudes about forgiveness and positive thought but stubbornly clings to grudges. He’s not the one who looks bad in this. It’s a funny bit, and so long as you refuse to play, you’re the butt of it….You’re simply digging in your heels, being stubborn, petty and stupid.”
Oprah was still steamed about Letterman’s jokes over the years:
Top Ten Disturbing Examples of Violence on TV:
No. 6: Unknowing guest gets between Oprah and the buffet
Top Ten Least Popular Tourist Attractions:
No. 3: The Grand Ole Oprah
Top Ten Death-Defying Stunts Robbie Knievel Won’t Perform:
No. 8: Screwing up Oprah Winfrey’s lunch order
Top Ten Things You Don’t Want to Hear from a Guy in a Sports Bar:
No. 1: “Oops—time for Oprah.”
Top Ten Things Columbus Would Say About America If He Were Alive Today:
No. 6: “How did you come to choose the leader you call Oprah?”
Top Ten Dr. Phil Tips for Interviewing Oprah:
No. 4: Grovel
Rapprochement came on December 1, 2005, when Oprah finally agreed to appear on Letterman’s show and then allowed him to escort her to the Broadway premiere of The Color Purple, prompting People to surmise:
And now, ladies and gentlemen, the Top Ten Most Likely Reasons Why Oprah Winfrey Ended Her 16-year Rift with David Letterman and Agreed to Appear on His CBS Late Show December 1, 2005:
No. 10: She is producing a Broadway musical, The Color Purple, across the street.
Nos. 9–1: See No. 10.
“At last our long national nightmare is over,” said The Kansas City Star.
Letterman behaved like a starstruck schoolboy. “It means a great deal to me, and I’m just very happy you’re here,” he gushed to Oprah. “You have meant something to the lives of people.”
An estimated 13.5 million people stayed up to watch that night, giving Letterman his biggest audience in more than a decade. The next day Washington Post TV writer Lisa de Moraes observed: “Letterman had become that which he once mocked. An Opraholic.”
It wasn’t simply a late-night comic who wanted to bathe in the reflected glory of Oprah Winfrey. To promote his 1,008-page memoir, My Life, former president Bill Clinton appeared on her show (June 22, 2004), sat with her for her Oxygen segment Oprah After the Show, and, hugging her and holding hands, took her on an extended tour of his home in Chappaqua, New York, to accompany a long interview in O magazine. On the show, Oprah made a point of saying that “nothing was off-limits,” as she directed the former president to read all the pages dealing with his sexual indiscretions.
“What were your feelings toward Hillary during those many times you betrayed her?” she asked.
“I always loved her a lot,” he said, “but not always well.”
“Weren’t you afraid of getting caught?”
Clinton dodged the question, saying he was in a “titanic struggle” with a Republican Congress, but Oprah pressed.
“You didn’t expect you’d be caught?”
“No, I did not,” he finally admitted.
She had packed the audience with young, pretty women, whom Jeff Simon described in The Buffalo News as looking at Clinton at certain moments “the way they’d look at a chocolate sundae; at others, the way they’d look at an infant’s first steps to the couch.”
Oprah’s ties to Clinton were strong. She attended his inauguration in 1993 and his first state dinner in 1994. In December 1993 she stood by his side in the White House as he signed the National Child Protection Act to establish a database network for all indictments and convictions on child abuse and sexual molestation. This law was known informally as the “Oprah Bill.”
Both Southerners from broken homes, Bill Clinton and Oprah Winfrey had a great deal in common. Each had risen from roots of meager expectations to achieve worldwide success based on a superlative ability to communicate. Both had well-publicized weight problems and were, in the words of Clinton, “secret keepers,” who knew how to live parallel lives—one in public, the other in private. Appearing together, they were mesmerizing. He gave her the second-highest overnight rating of the season, and she gave him a boost in book sales. It was a mutually admiring and advantageous relationship until July 27, 2004, when a young man running for the U.S. Senate gave the speech of his life at the Democratic National Convention. That evening Barack Obama’s soaring rhetoric and inspiring message rocked the convention and swept him into the hot strobes of national recognition. Among those leaping with joy was Oprah, deeply moved by his magical delivery. “It was one of the most extraordinary speeches I’ve ever heard,” she told him later. “There’s a line in The Autobiography of Miss Jane Pittman [a 1974 TV movie based on Ernest J. Gaines’s novel] when Jane is hol
ding a baby and asking, ‘Will you be the one?’ While you were speaking, I was alone in my sitting room cheering and saying, ‘I think this is the one.’ ”
After that speech, Oprah, who barely knew the Obamas, asked to interview them for the November issue of O, which strategically hit the stands days before the election that sent him to Washington as only the third African American to sit in the U.S. Senate since Reconstruction. By then Oprah had embraced the young senator as “my favorite guy.” She introduced him to her viewers in January 2005 as part of a show titled “Living the American Dream.” She honored his wife, Michelle, a few months later by including her as a “young ’un” during “The Legends Weekend,” and the following year she publicly endorsed him for president, months before he had endorsed himself.
During his Senate campaign, Obama had opposed the Iraq War as unnecessary, and by then Oprah, too, had changed her stance. Subsequently, she invited the esteemed New York Times columnist Frank Rich on her show (October 12, 2006) to discuss his book The Greatest Story Ever Sold: The Decline and Fall of Truth from 9/11 to Katrina, which indicted the Bush administration for selling the war to the country on false premises. Entitled “Truth in America,” the show included an appearance by Roy Peter Clark, senior scholar of the Poynter Institute, to discuss looking at the world from different points of view. He later reported in his online column that Oprah was dynamic, intelligent, funny, charismatic, and beloved by the women in her audience. “She walked out onto the stage, before the cameras started rolling, holding her shoes in her hand, a very down-to-earth image, but when she sat down, her shoe person rushed onstage, knelt down, and put them on for her. A coronation of sorts, if you can crown someone’s feet.”
At Fox News, Bill O’Reilly was going postal over Oprah devoting her entire show to Frank Rich. “She has declined to interview me, even though I had four number one bestselling books,” O’Reilly fumed. He went on the air four nights later with a segment “Is Oprah Fair and Balanced?” during which he claimed that Oprah was “leaning left,” with her liberal guests far out numbering her conservative guests. He said Oprah was being dishonest with her viewers about her politics. “Wouldn’t it be better if she looked everyone in the eye…?” A few days later Oprah invited Obama on her show (October 18, 2006) to talk about his book The Audacity of Hope.
“I know I don’t just speak for myself,” she said. “There are a lot of people who want to feel the audacity of hope, who want to feel that America can be a better place for everybody. There are a lot of people who would want you to run for the presidency of the United States. Would you consider that?”
Obama danced around the question to talk about the importance of the midterm elections. Then Oprah returned to the subject.
“So, if you ever would decide to run within the next five years—I’m going to have this show for five more years—would you announce on this show?”
“I don’t think I could say no to you.”
“Okay. Okay. So if you ever, ever decided that you would.”
“Oprah, you’re my girl.”
“Okay. That’s all I ask.”
“Fair enough.”
Bill O’Reilly was nearly apoplectic. He, too, had a book (Culture Warrior) to promote, and Oprah had “declined” to have him on her show. “He was so mad that he picked up the phone, called Oprah himself, told her she had no right to be so one-sided by having ‘a Bush hater like Frank Rich’ on to trash the president of the United States,” recalled a Doubleday publicist. “O’Reilly demanded that she be fair and let him come on her show with his book….He absolutely browbeat her and Oprah was so cowed that she agreed to have him on.”
The show (October 27, 2006), titled “Oprah’s Town Hall with Bill O’Reilly,” with a mostly male audience, allowed O’Reilly to rail against the “secular progressive movement,” or “SPs,” as he called them, which he said consisted of Frank Rich, the American Civil Liberties Union, George Clooney, Hollywood, Holland, mall zombies, the Democratic Party, the FBI, the Clintons, and The New York Times. Traditionalists, on the other hand, included “good folks” like him, President Bush, blue-collar towns, the working class, the little man, people who call Christmas Christmas, and Oprah. At the end of the hour, O’Reilly said, “This is the best show I’ve been on.”
Having proven to Bill O’Reilly she was fair and balanced, Oprah now made a decision that would put her at odds with Fox News as well as the Clinton wing of the Democratic Party. Feeling she had found “the One,” she decided to publicly embrace Barack Obama to the exclusion of all other presidential candidates. She had not been happy with those who suggested her show in 2000 had given George W. Bush a winning edge, so this time around she decided to give her powerful platform to only her “favorite guy.”
“If everybody knows I’m for Barack, it would be really disingenuous of me to be sitting up there interviewing other people as though…pretending to be objective,” she said. “So I won’t be doing anybody, because of that, on my show.”
As a talent scout without peer, Oprah recognized telegenic magic when she saw it. After all, she had introduced Dr. Phil, Rachael Ray, and Dr. Oz to America, and their talk shows, all of which she launched, had succeeded beyond industry expectations. The same instincts now drove her to put all her political cards on the table. It was a daring gamble, because Hillary Clinton was expected to be the Democratic nominee, and in going against the first woman with impressive credentials and immense backing who actually had a chance of winning, Oprah stood to alienate many of her female viewers. In supporting Obama, she was criticized for backing her race over her gender, while most of her African American friends supported Hillary Clinton.
Maya Angelou, Henry Louis Gates, Jr., Quincy Jones, and Andrew Young felt they owed their allegiance to Senator Clinton because, in the words of Gates, it was Bill Clinton “who brought us to the table.” Standing with Oprah, though, were Gayle King and Stedman Graham, a conservative Republican; plus her father, Vernon Winfrey, who pointed to the Obama poster on his barbershop wall. “I’m supporting him on the issues….Oprah might be supporting him for something else.” He chuckled about his daughter’s obvious crush on the Illinois senator, an inference that sprang from her flirtatious body language whenever she was around him—what her father called “her adoring eyes and all…I can tell you that Stedman isn’t getting any of that.”
Oprah’s best friend from high school agreed. “Obama is everything she ever wanted,” said Luvenia Harrison Butler. “Light-skinned and Ivy-Leagued.”
Late-night comics chimed in as well. “Over the weekend, Obama celebrated his wedding anniversary,” noted Conan O’Brien. “He went out for a romantic candlelit dinner with just his wife and Oprah.”
Obama’s influence on Oprah was not lost on anyone in Chicago, either. “When Paula Crown needed a star to appear at the Children’s Circle of Care benefit, she went to Barack, and he persuaded Oprah to speak,” said one of the city’s philanthropists. “Otherwise, we would never have gotten her, and she made the evening a smashing success.”
By endorsing Barack Obama for president, Oprah staked out a position that would subject her to criticism and partisan rebuke. “It was awful for her at one point,” recalled Alice Walker. “I remember when she and Gayle came to a wedding at the Bel-Air hotel….It was shortly after Oprah had refused to have Sarah Palin on her show, and the Republican women in Florida decided to boycott Oprah….She had tears in her eyes when she told us how they called her the N word.”
Oprah later mentioned the backlash. “I got some hate calls [that were] ‘Go back to Africa,’ ‘We gonna lynch you bad,’ ” she said. “I wasn’t snubbing Sarah Palin. I was just holding true to the policy that I had set for myself [not to invite other candidates on the show].” Two days after the election she invited Tina Fey, the comedienne who had filleted Sarah Palin with her dead-on imitation of the Alaska governor on Saturday Night Live. “I was in Denver—I had just attended the big speech Barack Obama gave—and
the next day was when Senator John McCain announced Sarah Palin,” Oprah recalled. “I said, ‘Oh, my god. She’s Tina Fey.’ ”
To appease Republicans after the election, Oprah said she would be happy to ask Sarah Palin to be on the show. “I went and tried to talk to Sarah Palin, and instead she talked to Greta Van Susteren. She talked to Matt Lauer. She talked to Larry King, but she didn’t talk to me,” said Oprah. “But maybe she’ll talk to me [when] she has a book deal.” Sure enough, Palin launched publication of her memoir with Oprah on November 16, 2009, leading to Oprah’s highest ratings in two years.
“Oprah was all about wooing back conservative viewers she’d lost when she endorsed Barack Obama for president,” wrote Lisa de Moraes in The Washington Post, so she veered away from controversial subjects. The next day she interviewed porn superstar Jenna Jameson, who wrote How to Make Love Like a Porn Star, but the media was more interested in politics than pornography. Two days after the Sarah Palin show, Tina Brown pounded Oprah in The Daily Beast: “She opened up with whether Palin thought she had snubbed her during the ’08 campaign by not asking her on the show. You could see Palin thinking as we in the audience were, ‘Huh? Why the eff are we wasting time talking about you?’ ”
Before the 2008 presidential election, Oprah was so determined to preserve her platform for Obama that when Bill Clinton returned to her show on September 4, 2007, to promote his second book, Giving, she made a point of telling viewers that he had called her himself, asking to appear. Months later the former president shrugged off Oprah’s lack of support for his wife. “Oprah is from Chicago,” Clinton said. “She was never going to be for anybody but Obama.”
The timing of Clinton’s second appearance on Oprah’s show was politically sensitive, because everyone knew that four days later she was hosting a huge fund-raiser for Obama at “The Promised Land,” her forty-two-acre estate in Montecito. The event, planned to accommodate at least sixteen hundred people paying $2,300 apiece, was trumpeted as one of the largest political fund-raisers in history. One late-night comic joked, “Oprah’s fund-raiser is projected to raise three million dollars; two million of which is to come from the ‘Dunk Stedman’ booth.”