Sweater, Lafayette 148 ($448). Nordstrom, 55 E. Grand Ave., 312-464-1515. Tunic, Eileen Fisher ($148). 108 N. State St., 312-578-0932. Leggings, Spanx ($72). Saks Fifth Avenue, 700 N. Michigan Ave., 312-944-6500. Necklaces, O’Donnell’s own. Boots, Prada ($950). Saks Fifth Avenue, see above
Rosie O’Donnell may prefer to wear Crocs, but there’s no denying that she cleans up well—provided she doesn’t dress herself. Her photo shoot at the Chicago Shakespeare Theater on Navy Pier goes well for one main reason: The photographer is fast enough to finish before O’Donnell has exhausted the Fiddler on the Roof songbook. Singing, she loves. Glamour? “I hate it,” says O’Donnell.
Once upon a time she tried to fight the makeovers. “I have done that, but my publicist and everyone else gets in a hissy fit,” she explains. “They’re like, ‘You look like you don’t care.’ So, you know, I gave up. I gave in.” At any rate, it’s hard to argue with the results. “Holy crap, I look good in these,” O’Donnell says of the pictures.
Taking Over in the Land of Oprah
And they’re for a good cause: to promote The Rosie Show, an eclectic mix of funny people, rowdy music, game-show silliness, reality-show segments, and audience interaction. When Oprah moved out of her Near West Side Harpo Studios, O’Donnell moved in. “She gave me the keys to this huge car, right?” says the New Yorker–turned–Chicagoan. Now The Rosie Show is OWN’s (Oprah Winfrey Network) best hope for finding its audience—if the audience can find The Rosie Show, that is.
“People come up to me and say, I can’t find you,” says O’Donnell. “And I’m like, ‘Call your cable provider. I don’t know where you live. What do you have, digital? I don’t know what channel it is.’”
Whatever the channel, the show airs live weeknights at 6 pm from the sacred studio. Some of Oprah’s former employees remain, but some things have changed. For instance, the star’s—and staff’s—children are often in the office. “Yesterday I got to hold a baby for, like, an hour during a meeting,” says O’Donnell. “A newborn baby. I was thinking, This is the greatest job in the world. You can have a staff member come in and say, ‘Here!’”
Prior to launching The Rosie Show, O’Donnell had a deal all lined up with NBC to return to TV, but she hesitated to sign it. “I was nervous about it because the Jay Leno/Conan [O’Brien] thing had just happened, and I was feeling like corporations don’t really care about people, and the integrity level is just based on numbers and ratings. I didn’t know if I could go back into shark-infested waters.”
So when Oprah called O’Donnell to confirm that she was interested in doing a show for OWN, O’Donnell was overjoyed. “Her network was the reason I wanted to be back on TV,” says O’Donnell. “I’m turning 50. I was home for a decade [raising kids], and that’s a long time.” She has enough experience to know to ignore the ratings for now. “It’s a network that’s just been born,” says O’Donnell of OWN. “It took CNN, what, five years to become a relevant force in the media world? And the same with Bravo—[it was] around for 23 years before Queer Eye for the Straight Guy hit. I’m thrilled to be at the ground level and growing as the network grows. I believe in what Oprah stands for and what we’re doing here.”
O’Donnell’s first successful talk show debuted in 1996, before she had come out publicly as a lesbian. “Initially nobody really asked [if I was gay],” says O’Donnell. “This was before the Internet, before Perez Hilton. It’s all changed in the last 20 years.” In 2006 O’Donnell signed on as moderator of The View, creating buzz for the show with her liberal passions and sparring matches with conservative cohost Elisabeth Hasselbeck. Ratings rose by more than 17 percent, but so did O’Donnell’s quick temper. She parted ways with the show with just about everyone’s feelings hurt.
It was a time when O’Donnell preferred to be at home anyway, with then future wife Kelli Carpenter (they divorced in 2007) and their growing family. O’Donnell, who lost her own mother at age 10, adopted Parker, 16, Chelsea, 14, and Blake, 12 as babies. Vivienne Rose was conceived via artificial insemination and was born to Carpenter in 2002. O’Donnell became a foster parent, too, and says she wants even more kids.
