Roseann O'Donnell, a mother of five, dies of breast cancer, leaving behind her husband Edward to raise their children. She is buried on her daughter Rosie's eleventh birthday, but Rosie and her siblings do not attend the funeral. "Most mothers don't die when you're 10 years old," O'Donnell tells Entertainment Weekly. She deals with her grief through watching TV, which "became a surrogate parent, a friend," she tells the Washington Post in 1997.
O'Donnell, 16, makes her debut as a stand-up comedian open mike night at open mike night at the Mineola's Ground Round restaurant and performs again at the East Side Comedy Club in Huntington, Long Island. Club manager Richie Minervini tells the New York Times, "She came in and went on stage, and I'll tell you what. She had talent right off the bat. She wasn't really funny but she had a charisma. She had a presence. She had a desire."
After dropping out of college at Dickinson College in Pennsylvania and Boston University, O'Donnell begins touring comedy clubs. She makes her television debut on the hit talent show Star Search and wins the comedy competition five times. Although she loses in the finals, O'Donnell wins $14,000 – enough to move to L.A.
O'Donnell makes her acting debut on NBC's Gimme a Break as Nell Carter and Joey Lawrence's neighbor. The show is cancelled in 1987, and O'Donnell is hired as a VJ for VH1, later hosting and producing its comedian showcase Stand-Up Spotlight for four years.
O'Donnell costars in FOX's sitcom Stand By Your Man with Melissa Gilbert of Little House on the Prairie fame. They play working-class sisters whose husbands are in prison for a bank robbery, but the show never gains an audience. "It got cancelled because the Richard Simmons Deal-A-Meal program got higher ratings," O'Donnell tells Entertainment Weekly.
O'Donnell stars in her first movie, A League of Their Own, about a 1940s all-women baseball league, starring Tom Hanks, Geena Davis and Madonna. The film's director Penny Marshall tells PEOPLE, "The part was originally for a hot, sexy girl, but I liked Rosie so much we changed the story to suit her. She can make anything funny." O'Donnell adds, "If there's one thing I can do better than Meryl Streep and Glenn Close, it's play baseball." O'Donnell goes on to star as Meg Ryan's best friend in Sleepless in Seattle, and with Richard Dreyfuss and Emilio Estevez in Another Stakeout.
After portraying best friends in A League of Their Own, O'Donnell and Madonna become close friends and bond over losing their mothers at a young age. "I know what it's like to go to your mother's grave and see your own name. I knew that if I met her we would be friends," O'Donnell tells Entertainment Weekly. Madonna tells Life, "Rosie and I speak the language of hurt people."
O'Donnell fulfills one of her dreams by starring in the Broadway musical Grease! as Betty Rizzo. "I auditioned and said, 'Listen, I'm not the best singer and I'm not the best dancer,'" O'Donnell tells USA Today. "'But I'm gonna give ya 100 percent and I'm going to sell tickets for ya. So if I were you, I'd cast me.' And then I left. And they did. Thankfully." O'Donnell was on the money: her name on the playbill sells $4 million in ticket sales before the show's premiere. In 2002, she returns to Broadway as the Cat in the Hat in the musical Seussical.
The comedian continues her film career, playing Betty Rubble in the live-action version of The Flintstones with Halle Berry and in Now and Then with Demi Moore. However, she takes on a new role as mother when she adopts son, Parker Jaren. "When he looks at me, I can finally see my own mother as a woman, not just as my mom," she tells Redbook in 1997. "I feel closer to her than I have in a long time. I finally understand just how much she loved me. I realize that she felt, for me, the things I feel for him."
While shooting the film adaptation of the classic children's book Harriet the Spy, O'Donnell realizes she couldn't be a full-time mom and make movies. She pitches a daytime variety show, like the Merv Griffin and Mike Douglas shows she grew up watching, to Warner Bros. Warners bites and O'Donnell becomes host and executive producer of The Rosie O'Donnell Show. The syndicated talk show provides her with regular hours, a home base in New York and a reported $4.5 million salary.
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