Oprah and Rosie
Photo: Matthew Ralston
She's been a stand-up comic, a veejay, an actress, and a talk show host—and with her upcoming show on OWN, she's giving that last one a whole new spin. Now the mother of four opens up to Oprah about life after divorce, what turning 50 will mean to her, and how great it feels to have to wait for a table.
In 25 years of doing my show, only one competitor ever seriously challenged me in the ratings: Rosie O'Donnell. From the day Rosie took her place among the crowded field of talk show hosts, I knew she had that "It" thing: She was as sharp as she was authentic, as forthright as she was funny. During six seasons of NBC's The Rosie O'Donnell Show, she not only won 11 Emmys—she knew how to use her screen time to truly connect.

Nearly a decade after ending her show, Rosie returns to television this fall to do what she does best, entertaining and connecting again. The two of us have teamed up to create something brand-new: The Rosie Show, debuting October 10 at 7 P.M. on OWN. What's new about it? Rosie! So much has changed for her since she was last on TV.

In 1996 when she first walked onto her set, Rosie was the 34-year-old single mother of one adopted son. She'd already shown her talent on TV (as a VH1 veejay) and in movies (as the loudmouthed third baseman Doris Murphy in 1992's A League of Their Own), but she wasn't exactly a household name. And though everyone close to her knew she was gay, it wasn't something she talked about on TV.

Fifteen years later, Rosie is the mother of four children—Parker, 16, Chelsea, 14, Blake, 11, and Vivi, 8—and a vocal champion of gay rights. She came out to the world in 2002, by which time she'd been with her partner, Kelli Carpenter, for almost five years (the couple would later marry, in San Francisco). After leaving her TV show that same year, Rosie retreated to her home in Nyack, New York, to be a full-time mom—a dream she'd had since losing her own mother to cancer when she was only 10. But life, she says, "didn't go according to script." She and Kelli started to grow apart, and as they spent less time together and finally split, Rosie began inching back into the spotlight, becoming a wildly outspoken cohost of The View and later doing a radio show on Sirius XM.

Today, poised to launch her new TV show, she says she's in a completely new place. As the two of us sit down after our cover shoot in New York City, Rosie, who will turn 50 this spring, tells me she's never been more clear about who she is, what she wants to say—and how she can use her show as a gift to her viewers. This time, direct from Harpo—that's right, she's moved into my Chicago studios—you'll find a show featuring real people dealing with real issues, some celebrities, lots of fun and games, loads of laughter, and a frank-as-ever Rosie.

Next: Start reading the full interview
Oprah: As I've watched you over the years, I've always heard you talk about your children. But it wasn't until we were discussing whether to do the new show—when I came to see you in Nyack and actually sat in your house—that I recognized, Oh, yes, this family focus is really real.
Rosie: It's why I wanted to be successful—to have enough money to have children, to give them a life I didn't have, and then to be done when I was 39 or 40, because that's about how old my mother was when she died.

Oprah: You thought that was going to be your fate, too?
Rosie: I did. I had the sense that there was some sort of predetermined time limit on me. And every year after that has felt like extended play. You know when you play a video game like Grand Prix—well, you probably don't know this, Oprah, but sometimes you get an extra lap. That's what I've felt every year since I turned 39. Like, Oh my God, I got another one! Oprah: You always knew you were going to be a parent, even when you were a little girl growing up on Long Island.
Rosie: From the beginning. When I was 6 years old, I was always the one holding babies. When I got to be 18 and could sit at the adult table, I chose to sit at the kid table. The truth is, I'm a little socially awkward—with adults, I still need Relationship 101. But I was always comfortable around kids and always wanted a family of my own. When I started my first show, I said, "I'm going to quit in five years," because that's when Parker, my oldest son, would have been entering kindergarten. I ended up extending it to six years, but I knew that was the finish point. Even though they said, "We'll give you this and that," I told them, "There's nothing you could give me that would make me stay." My kids were starting school—I wanted to be there for all the things my mother missed.

Oprah: Because at that point you really understood what she missed.
Rosie: When I first held Parker, it hit me the most. I was like, Oh my God, she felt this [puts her hand over heart]—and then she knew she was dying and leaving five children with a man who I think she realized was incapable in many ways. What that must have felt like for her...

Oprah: Is there a part of you that's not in full gear for life because you're expecting not to make it?
Rosie: The opposite—I'm always in high gear because I know it could end at any moment. I'm trying to absorb everything—to the point where for a while I was really overdoing photos of my children. I just wanted to capture it all, but they started treating me like paparazzi—"Please, Mom, stop already!" Then I read a book about staying in the moment, and I stopped. Because if you put a lens here [motions to her eye], there's somehow a distancing, right?

Oprah: Yes. And in the Kodak moments, most people are taking pictures of the life they wish they were actually living.
Rosie: But you know what's interesting? Kelli came from a very debutante ball kind of family. It was like a life out of Dallas. All the photos in her house were of her family in the same outfits at the beach—which, to me, looked fake. But when I'd send pictures of the kids to Kelli's mother, she'd say to Kelli, "Why does she take the pictures when they have chocolate on their faces?"

Oprah: Because you like the chaos.
Rosie: That's when I'm like, "Click!" There was a time when I wanted the porcelain veneer. But as I grew up, I realized, wow, the beauty is in the cracks.

Oprah: And once you start looking, you realize the cracks are everywhere.
Rosie: Like with my mother dying. I was so hung up for so long on the story of that loss that I never took the time to realize how well she must have mothered me in order for me to have the desire and ability to mother the way I do. That had to come from somewhere. And now I actually feel a little lost because I never got to watch her mothering teens.

Oprah: The teen years have thrown you.
Rosie: Not so much with my son Parker. I'm madly in love with him. I would die for any of my children, and, more importantly, I would live for any of them. But there's something about Parker. When I look at him, I realize that my whole life is B.P. or A.P.—before him or after. Because he was the first. Because when you go from being a nonparent to being a parent, your entire paradigm shifts. So as much as my mother's death was a dividing line in my life—March 17, 1973—May 25, 1995, is when the lights came back on. Color entered the picture again.

Oprah: You and Kelli married in 2004 and divorced in 2008. I read that your split was one of the most difficult things you've ever had to deal with.
Rosie: Humbling. And humiliating.

Oprah: Because it felt like you failed?
Rosie: In the O'Donnell family, no one had ever been divorced. At 33 I adopted Parker. Then I adopted Chelsea. Then I met Kelli. And the plan was that you stay together forever. But when I left my show and when Vivi was born—three of the children are adopted, and Kelli gave birth to Vivi—everything shifted. I was no longer on TV. I had a lot of time. I was at home, trying to come down from the rarefied air at the top of the mountain and regain some kind of authenticity.
Oprah: At sea level.
Rosie: Yeah. And it wasn't clicking for either of us. We didn't like the same stuff. I would be in the pool every day with the children. And when we were in Miami, where I also have a home, I'd go out on my boat—I could spend ten hours a day on my boat, looking for dolphins. But Kelli didn't really like the boat or the pool. She plays tennis.

Oprah: And you hadn't noticed these differences when you were doing the show?
Rosie: I didn't have a lot of time. I was working, working, working. Then when we'd have a week hiatus, I was like, "Come on, we're all going down to Miami!" If Kelli was out shopping, it didn't matter—I'd just go with the kids. But later, when the separate interests became day after day, I found myself lonely—as she did, too. She wanted to play tennis at the country club, and I don't do country clubs. I tried. They made an exception for a gay family, and we joined. It was a big thing: "They let in a gay family—whoo!" So I show up to play with her, and somebody comes out and says, "You can't play unless you have tennis whites." I said, "Excuse me? I have to get dressed to come and play tennis at a club that I pay ownership fees to?" That was the last time I went. It's a different culture. I just didn't fit.

Next: Rosie discusses hormones, coming out, and reaching a new place in her journey
Oprah: I've seen this time and again, where one person's been out moving around in the world, and now you're in the same environment—after you'd gotten used to a life where the other person was revolving around you.
Rosie: Correct. And then I tried to show my gratitude to her by helping her start the cruise company [R Family Vacations, which launched in 2003 and runs cruises for gay and lesbian families]. Like, "Here's your company, we'll do the gay family cruises!" But then suddenly she was working a lot. I remember joking about it: "Yeah, this is a great life decision I made. I could be going, 'Honey, I'm hemorrhaging from my leg,' and she's like, 'That's nice, I'm booking a penthouse—can you wait a second?'"

There's also the fact that when we got together, Kelli was only 30, and it was her first long-term relationship. Before me, she was not out to her family. I kind of forced them to accept that she was gay.

Oprah: Were you always out?
Rosie: To everybody in my personal life, yes. The only people who didn't know were the audience. But they kind of knew, because Kelli sat next to me at the Emmys.

Oprah: Before you started the show, was there a discussion about whether you should be public about it?
Rosie: Before I signed the deal, I sat down with Warner Brothers and said, "I want you to know that I'm gay—and I don't imagine that I would talk about it." Remember, this is pre–Will & Grace. Pre–Ellen DeGeneres coming out.

Oprah: Pre-Ellen?
Rosie: Yes. This is 1995, okay? The culture wasn't talking so much about gay anything.

Oprah: I understand. We've come a long way since then. And, speaking generally now, you seem to have come a long way, too. You seem more "you" than you've ever been. In fact, part of the reason I think this partnership of ours is now possible is that you've reached a new place in your journey.
Rosie: Totally true.

Oprah: When I was at your house in Nyack, you told me that getting some hormones had changed your life.
Rosie: Yes. I had, like, zero estrogen. And since I got some, I've been able to function more normally. I've stopped being so angry. You know, I think I had a lot more rage than I was aware of. But I've gotten back access to my other feelings. I'm not cut off from my emotions anymore.

Oprah: So it helped with the rage.
Rosie: The rage has gone away. Even with something like the Casey Anthony trial—normally I would obsess about that. I would be so furious. But I didn't even go near it. There's been a healing.

Oprah: Did getting hormones also help with what you thought was depression?
Rosie: A lot. TM [transcendental meditation] also helps: just being still and resetting my internal hard drive twice a day.

Oprah: You seem more accepting of yourself than you have been in the past.
Rosie: Yes. Of other people, too. As you say, I'm trying to stop expecting the past to have been different. And I've learned the necessity of not "writing stories" about other people before I know them.

Oprah: So you really are in a new place.
Rosie: I am. And part of it is the divorce.

Oprah: Did it free you in some way?
Rosie: It has freed me from what I thought was the prescription for happiness: Get married, have children, stay married. When my kids used to act out, I'd joke, "This is not in the script!" But when Parker was 12, he said, "News flash, Mom—we don't have a script."

Next: Why her new show will be different
Oprah: Was it freeing to leave the show, too? Or did you miss the success that went with it?
Rosie: You know what I missed? The staff. I loved them. Whenever there was a goodbye party for someone who was leaving, I'd always sneak away because I don't like endings. I want everyone to stay around forever. So I miss the people. But I didn't miss—

Oprah: The day-to-day.
Rosie: Right. All of a sudden I had time to do the things I'd been too busy for. Of course, there are some things I'll never get back—like the normality of life pre-fame. I've had to come to terms with the fact that fame is like a tattoo—it doesn't go away. For a while, I was able to keep it separate. I'd see a magazine cover and go, "Oh, there's Rosie O'Donnell." Then I'd go home to my bubble where no one knew I was with Kelli, and we had these kids. I loved it. But eventually my world opened up, and it took some adjusting. The problem is, fame is held up as the brass ring, the place you want to get to. Any kind of critique of it—

Oprah: Nobody can hear.
Rosie: It sounds like sour grapes. But I'm telling you, you're missing the real moments of your life while craving this thing that doesn't allow you to have them anymore. And you should cherish them while you have them. Those real moments.

Oprah: So why did you make the decision to come back to television?
Rosie: After I divorced, I didn't have my kids half the time. Which was horrifying to me.

Oprah: Because you share custody.
Rosie: Yes. I remember sitting in my house going, "I need something to do." I tried radio. I enjoyed it. Then I did your show in January 2010. I thought, Oh my God, I remember why I love it! The excitement of building up to it, your staff, the whole vibe there. I was actually on the verge of signing a new deal with NBC, and—this probably sounds kiss-assy, but it's true—just before I was about to sign, I remember saying to my agent, "Doesn't Oprah have her own channel? Can we call there?" If I was going back to entertaining, I wanted to work with you.

Oprah: Thank you for saying that. I'm so happy you chose OWN. On your show, what do you want to be different this time?
Rosie: It's already different. I'm different. When I started the last show, I had a baby who took his first steps in my office. I had never met people like Tom Cruise or Barbra Streisand. Since then, they've both stayed at my home in Miami. It took a while for me to get a grip on the idea that, Oh, wow, you are in the club. Everyone I know who's in the club feels they're not a member—even the biggest stars you can name.

Oprah: Interesting, isn't it?
Rosie: When I finally realized that, I cut myself a break. I'd always been able to see that everyone else's success was merited—but it seemed like mine must be a fluke.

Oprah: When did you get that yours wasn't a fluke—after your show?
Rosie: Totally. I got that people liked me.

Oprah: Newsweek called you "The Queen of Nice" on its cover.
Rosie: They must have never seen my stand-up act! Because comedy is based in rage, you know. Anyway, I was only nice because someone had been killed after being on The Jenny Jones Show the year before I started. And somebody broke Geraldo's nose. You were the only one not hurting people. So compared to most people on TV then, sure, I was nice. But I never felt it was a label that fit. And it's funny, because when I was first on TV, people would see me at the mall and go, "What's the matter?" I was like, "Nothing, why?" "You look like you're mad." "That's because you're used to seeing me like this [plasters on a smile] on the show!" Whereas my normal face—ready, I'm about to give it to you!—looks pissed off, doesn't it?

Oprah: We call that your resting face.
Rosie: My resting face.

Oprah: So what did you think when you saw that Newsweek cover?
Rosie: I remember holding it up on my show and saying, "This is going to bite me in the ass." What, exactly, is "nice"? For someone to be innately kind or empathetic is one thing. But nice?

Oprah: What does it really mean?
Rosie: So I dissociated myself from it. I didn't participate much in my own celebrity—I tried to downplay it. I study with a spiritual woman, and she once told me, "You like to say you shop at Target and this and that—but you're a millionaire." There was a noncongruency, in other words. When you start approaching your 50s, though, you get congruent. The life you're living becomes more reflective of your reality.
Oprah: Absolutely.
Rosie: I didn't really know who I was. When I divorced and my plan fell apart, I had to reframe the picture.

Oprah: Exactly. So your show will be different because you are different.
Rosie: Yes, but that's not the only difference. Since I've been off the air, television has become saturated with celebrities. In America we're addicted in a way that's embarrassing. So it's not going to be all about celebrity. It'll be a celebration of humanity, of connection, of authenticity and love. Because it's on at 7, we're going to do a hybrid between a late-night show and a daytime show. We'll incorporate the audience. We've come up with a new kind of talk show that mixes the old single-topic format with fun and social media. So it will have a reality feel. We'll have to get the kinks out, but the same way I knew the first one would work, I know this will work.

Next: Making the transition to Chicago—and learning how to be un-famous
Oprah: I've worried about your being lonely in the transition from New York to Chicago.
Rosie: I have, too. It's a great challenge for me. I have to be vulnerable and open myself up again. But that's a hugely life-affirming, fueling, spiritual thing, right?

Oprah: Yes.
Rosie: It would be very easy to live in my comfort zone and just stay in Nyack painting and doing crafts. But I already did that—for a whole decade. Now that I'm in Chicago, I've already felt a difference. Sometimes you go outside and get beat up by New York. The city accosts you. But being in the middle of Chicago, it's peaceful.

Oprah: Isn't it?
Rosie: The other day in Chicago, I went to Millennium Park, to a Broadway concert. I'm acting as if I'm allowed to live like this, and the people in the city are allowing me.

Oprah: That's exactly the way I've lived there for 25 years.
Rosie: I even had to wait for a table at Gino's East. I walked in, and they said, "Name?" I said, "Rosie." They said, "Hi, Rosie. Welcome to Chicago. Sit down, it'll be 20 minutes." It wasn't like there was a line outside—and there were empty tables, too! I thought, Well, this is going to take some getting used to, but it's a good lesson.

Oprah: The one thing you don't do when you're a celebrity is wait!
Rosie: Ever. When celebrities become unfamous, someone should teach them how to wait in line—and order from a menu! When you're famous and you go to a restaurant, the chef whips up whatever you feel like eating, even if it's not something they serve. Eventually, you're walking in anywhere—

Oprah: And expecting to get exactly what you want.
Rosie: You go into McDonald's and say, "Can I have a pizza?" You start to live that way. But you know, more is not always better. That took me a long time to find out. So being in Chicago is like a new beginning for me. For the first time in a long time, I'm excited.
Oprah: Yeah?
Rosie: Yeah. The first night in Chicago, it was hard for me to sleep.
Oprah: Oh, that's good!
Rosie: I'm feeling rejuvenated. I'm nervous about starting the show, which is the greatest way to be. When you don't have that anticipation of wanting to do well, then you might as well not be doing it at all.

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