Beloved, a film adapted from a Toni Morrison novel, opens with Winfrey acting as both star and producer. While prepping for the film, she gets into the mindset of her character, a former slave in a post-Civil War setting, with a real-life reenactment. The role-playing was scheduled to last 48 hours, but Winfrey calls it off after six. "The guy in the reenactment [said], 'Nigger, you belong to me,'" she tells the Bergen Record of her time toiling in fields and running through woods for a faux-escape. "I felt shock waves of pain, pain, pain."
Winfrey launches O, the Oprah Magazine. After discord arises among the editing staff, Winfrey flies them all to her home in Miami. "The retreat was to sync ourselves up," Winfrey tells The New York Times. Six years later the magazine hits a circulation of 2.6 million.
Winfrey launches her show's Wildest Dreams season and kicks it off by giving each of the 276 audience members a new Pontiac G6 car. A controversy arises when they have to pay almost $7,000 each in taxes for the gifts. "As soon as we heard [about the taxes,] we started working with the accountant to adjust our income taxes," Kyle Meyers, whose wife was in the audience, tells the Wisconsin State Journal. "But that's nothing compared to a new car. How could you complain about that?"
Winfrey chooses James Frey's memoir A Million Little Pieces for her book club. Four months later, she finds out parts of the book were made up and confronts him on air. "I feel duped, but more importantly I feel that you betrayed millions of readers," she says on her show.
Twenty years after starring in the film version of The Color Purple, Winfrey helps bring the story to Broadway. She appears on David Letterman's show the day the play opens to promote it, ending the 16-year rift that developed because, as she told Time in 2003, a previous appearance on Letterman's show made her uncomfortable.
In the August issue of her magazine, Winfrey denies rumors that she's having a romantic relationship with best friend Gayle King. "I understand why people think we're gay," Winfrey writes in O. "There isn't a definition in our culture for this kind of bond between women."
Winfrey opens the $40 million-plus Oprah Winfrey Leadership Academy for Girls. She chooses 152 of South Africa's neediest girls to attend. "This is the proudest, greatest day of my life," Winfrey says. In March, she opens a second school, and makes PEOPLE's Most Beautiful and Time's Most Influential lists. But, in October her academy is hit by allegations of abuse. Winfrey publicly apologizes to families and a former school matron is arrested on charges of physical and sexual abuse.
After topping the Hollywood Reporter's Women in Entertainment Power 100 list, Oprah confesses to tipping the scale at 200 lbs.–a 40-lb. weight gain from her slimmer self. "I'm mad at myself," she declares on the cover of her magazine's January issue. "I can't believe that after all these years, all the things I know how to do, I'm still talking about my weight."
Winfrey announces her plans to end her highly rated talk show in 2011 after 25 years, in an effort to prepare for the launch of her cable channel, OWN: The Oprah Winfrey Network. "I love this show," a teary-eyed Winfrey tells her audience. "This show has been my life and I love it enough to know when it's time to say goodbye."
With a New Year, there's a new Oprah, as the media mogul launches her TV network, OWN, to stellar ratings – a solid 1 million viewers on her inaugural evening. "I wanted to take the ideals of great television that we've established on the Oprah show and bring them to you through a variety of new shows 24/7," she says. "Every minute of this network has been hand-selected by me for you, the viewers."
BIOGRAPHY (top to bottom): Walt Disney Co./Everett; Bob Davis/AP; George Burns/Harpo Productions/AP; CBS/Landov; Arnold Turner/WireImage; George Burns/Harpo Productions/AP; Fred Prouser/Landov