Looking back at Rosie O'Donnell's career it's clear she's a restless woman. Comedienne … talk show queen … actor … author.
But at age 47 she may have finally found her calling.
"I think it's the best thing I've ever done in my career, without a doubt," she said.
Her crowning achievement, Rosie's Broadway Kids, is a program she created six years ago to bring musical theater to public school children in New York City.
"I was saved by the arts. And that life raft that took me to shore I wanted to get on it again," she said.
It's just one of many projects she's supported in her long history of philanthropy.
"I've read it's anywhere from in excess of $50 million that you've donated to various charities,' Roberts said.
"Yes, but I was very lucky to make a lot of money, more money than any human should make, I could tell you that. I have tremendous guilt issues about the money I have. And when I started making the money, I said to the money person, 'If I'm ever on the Forbes list of richest people, you're fired.'"
The program that started with just 40 children has grown now to more than 1,500 in 19 schools.
"What we do is, we go to the poorest fifth grades of the city, our own teachers, and provide a 17-week, in-class program to every fifth grader in that school."
David, a student at New York's P.S. 142, certainly enjoyed it: "We sing and we dance at the same time - It's pretty cool," he said. "It's actually really fun!"
Students who excel in the program are invited to continue to study musical theatre after school at the Maravel Arts Center, that Rosie built in Manhattan.
Krishawn said, "What I like to do the most is tap."
"Did you have any ambitions or any interests in tap before you started the program?" asked Roberts.
"No, I barely even knew tap exists!"
"It's regular kids doing theater, 'cause they love it and it's helping them feel better about who they are," said O'Donnell.
Rosie is hands-on at the Center. She knows every child's name and tries to learn about their lives.
"I've grown because now I'm a dancer, singer and actor," said Anthony. "I was never any of those."
Keira said, "I love it. Performing just lets me express everything that I've been shutting up all day. And coming here, it's like freedom, yeah."
When Rosie was a child, her mother introduced her to the theatre by taking her to Broadway productions. The experience would be life-changing for the girl from Commack, Long Island.
She remembers Bette Midler - now a personal friend - made a big impression.
"I remember seeing that and looking at the stage and going, 'I want to be her,'" she said. "I wanted to 'I Dream of Jeanie' be her, because I'd never seen anything like it.
Broadway and dreams of performing there were the bright spots in an otherwise dark childhood.
She says an intruder would slip into her bedroom at night - but her mother refused to believe her.
"I told her somebody came in my room again. And she said, 'You lie like a rug.' And I remember thinking, 'Rugs can't talk!' You know, eight-year-old kids don't understand metaphors."
"Were your molested?" asked Roberts.
"Somebody came in my room at night, and that's what I told my mom. And like many mothers, that a hard thing to deal with. And sadly, she died a few years later."
Three days before Rosie's 11th birthday, her mother Roseann died of breast cancer. It was, she said, "the defining moment of my life."
So painful, Rosie began to intentionally harm herself.
"You broke bones in your hand with a baseball bat?"
"I would take a bat and, like, literally hit it until I broke the bone," O'Donnell said. "And I could tell when I broke the bone. Your inner pain is so unbearable that to make it a physical, outer pain, somehow provides comfort."
Rosie's math teacher, Pat Maravel (whom she named the arts center after) became her second mother.
"She was the first person to hug me. She was the first person to say, 'I love you.'"
"You mean outside your family?"
"No one said 'I love you' in our house growing up. I don't know what would have happened to me if I didn't have her."
Over time, she began putting her life back together, and by her senior year of high school, Rosie was class president and homecoming queen.
"How does this wounded girl transform herself into the most popular girl in high school?" Roberts asked.
"We were funny. The O'Donnells are a funny group, you know? You could talk about anything at the dinner table, as long as you could make it a joke."
Rosie tried college, but comedy was her calling . . .
"Describe your sense of humor then," Roberts asked.
"I used to take Jerry Seinfeld's cadence, because he was the most popular comedian at the time. So everybody talked like Jerry. So I was like, 'I got a water bed today. I had to catch a wave to answer the phone.'"
She broke into television in the '80s on "Star Search,' and then made film debut in 1992's "A League of Their Own," as Madonna's best friend. She said the transition to acting was great "because I could play baseball."
Soon she was playing Meg Ryan's best friend in "Sleepless in Seattle," and a Stone-Age wife, Betty Ruble, in "The Flintstones."
But after adopting her first son, Parker, Rosie wanted the stability of a day job and created her own talk show.
She said she wasn't surprised that he audience could connect with her: "No, I thought it would be a hit."
With the daytime airwaves dominated then by tabloid shows, Rosie saw an opening.
"It was a free-for-all. It was a Jerry Springer festival of humiliation every day after school. So I knew that if you just gave them a little Merv Griffin, just a little Merv is all you need."
Her instincts were right. Rosie's playful, feel-good style won her a huge following. Newsweek crowned her The Queen of Nice.
"Well, even at the time I remember holding it up on the show and saying 'Queen of Nice'? Next year it's going to be the Queen of Fried Rice, this is gonna bite me in the ass. I held it up and said that."
Rosie's prediction came true.
In 2006, she joined the cast of "The View," and came out swinging, clashing with Elizabeth Hasselbeck and with Donald Trump. Her controversial comments drew ratings, but in the end it was a stormy and brief run.
(AP Photo/ABC, Yolanda Perez)
"I don't have a temper. I've never broken everything. I've never thrown a thing," she says. "But I have passion. If I feel passionate, you're going to know."
"How does it make you feel when your detractors say you're too loud, you're too abrasive, you're just too much?" Roberts asked.
"It's not really the detractors who say it, it's when the people I love say it. I mean, honestly, it's the people in my life who go, you know, 'Come on, gimme a break. It's too much, you know?'
"I know, but this is the model I came with, like, this is the hard drive."
"Now that you have some distance from the show, can you look at it differently?" Roberts asked.
"Yeah. Yep, I can."
"What were the lessons that you learned from that experience?"
"I learned that when you yell, nobody hears you. And that the best communicators have to live and present themselves in a peaceful manner. And that's gonna be a lifelong quest of mine, because I get so angry at the things that I think are unjust."
"After the show, you just kind of retreated. You concentrated on your blog, but we really didn't see much of you."
"No. I was trying to figure out what to do. And I'm still sort of there, tryin' to figure it out."
All concentrating on parenthood. Rosie and her partner Kelli have 4 children, whom they're raising outside New York City.
She's playing soccer mom. "Well, baseball mom this week. I'm a baseball mom. Sometimes a swimming mom."
She'll soon be juggling her mom duties with new projects. Next year Rosie plans to make her 4th appearance on Broadway in a stage adaptation of the Mickey Rooney-Judy Garland film, "Babes in Arms."
"This is what I dreamed of as a kid, to originate a role in a Broadway musical. Now for somebody who really can't sing, and really can't dance, that's a pretty big accomplishment!"
And after a career as a comedian, actress and talk show host, Rosie O'Donnell says she's touched all the bases.
"I realized all of my dreams."
"Now it's time to create new dreams?"
"I think that's what the school is doing for me. You know, I love going there. I love seeing those kids. It's back to my real life. It's back to the origins. Back to where I started."
For more info:
Rosie's Broadway Kids