O'Donnell receives a $3 million book advance from Warner Books to write a memoir. She uses the advance as seed money for her new foundation, For All Kids, which helps institute national standards for day care across the country. The foundation raises more than $60 million, and her memoir, Find Me, is released in April 2002, debuting at No. 2 on the New York Times Bestseller List.
The Rosie O'Donnell Show premieres to the highest ratings of any daytime talk show in the decade. The Washington Post dubs it Rosieville, "a place where every chat is a lovefest." In the first year, Hillary Clinton, Tom Cruise, Elton John, and Madonna are guests, and the show closely tails Oprah Winfrey in the ratings.
After being crowned the "Queen of Nice" by Newsweek, O'Donnell wins the Daytime Emmy for Outstanding Talk Show Host, beating Oprah. While she doesn't take home the award for Outstanding Talk Show this year (Winfrey wins the honor for the fourth year in a row), O'Donnell will dominate both categories in the coming years: she wins Outstanding Talk Show host for six consecutive years and Outstanding Talk Show for the next four.
O'Donnell hosts the Tony Awards and ratings leap nearly 50 percent from last year's telecast. "I believe Rosie has got our foot back in the door of popular American culture," Bill Evans, a Broadway press agent, tells the New York Times. O'Donnell hosts again in 1998 and 2000, and gets tapped to emcee the Grammy Awards in 1999 and 2000.
After adding a daughter, Chelsea Belle, to her brood, O'Donnell is introduced to marketing executive Kelli Carpenter by her brother Daniel. They begin dating, but O'Donnell doesn't come out as a lesbian publicly. Two years later, the couple adopts son, Blake Christopher, together. O'Donnell tells PEOPLE in 2002 that Carpenter "is a gift in my life."
After the Columbine High School massacre, O'Donnell becomes a strong anti-gun advocate and gets into a heated 10-minute debate with actor and NRA supporter Tom Selleck. "I came on your show to plug a movie (The Love Letter)," Selleck says on-air. "If you think it's proper to have a debate about the NRA, I'm trying to be fair with you. This is absurd." After the fight is televised, O'Donnell's four-year-old deal with Kmart comes under fire. Gun owners complain that she shouldn't be a spokesperson for one of America's largest gun retailers. That December, she gives up her Kmart deal.
After becoming editorial director of the monthly women's magazine McCall's in 2000, O'Donnell, with publisher Gruner+Jahr USA, renames the magazine Rosie. "I wanted a magazine that celebrates real women," she tells PEOPLE, "that understands that they care about more than their waistline or the latest makeup styles or fashions, that they want to be relevant and help each other and care about the world."
Although O'Donnell has privately acknowledged her sexuality for more than 20 years, she never came out publicly and finally does in an interview with ABC's Diane Sawyer. O'Donnell says her decision to talk about her sexuality was triggered by a gay couple, who were challenging a Florida law barring gay people from adoption. Two years later, gay newsmagazine The Advocate names her its person of the year.
After six years on air, O'Donnell (who earned an estimated $25 million a year) resigns to spend more time with her family. This comes amid negative press and reports that she is notoriously tough and difficult to work with. "You have to accept being vilified," she tells PEOPLE. "What I said to my [TV staff] when we left is, 'I pushed you really hard. But I hope you've raised the level for yourself and that you will jump higher.'"
After debuting a new, edgier short haircut (dubbed "the side mullet"), O'Donnell splits with her 16-month-old namesake magazine after months of fighting with her publisher Gruner+Jahr USA. "If I'm going to have my name and my brand on the corner of a magazine, it has to be my vision," she tells PEOPLE. "They [G & J] tried to say it no longer could be." O'Donnell is sued for $100 million by the publishing company, but she counter sues for $125 million. After a well-publicized legal battle, a judge rules that neither side deserves damages over the magazine's demise.
BIOGRAPHY (top to bottom): Frank Micelotta/Getty; Ron Galella/Wireimage; Chris Pizzello/Wireimage; Warner Bros.; Shannon Stapleton/Reuters/Corbis; AP