But Jackson does not look back on all of her childhood memories as fondly.
Living in the shadow of the Jackson 5, then the most famous family act in America, her father Joe Jackson took the reins when it came to her career.
Jackson, who once had dreams of going to college to study business law and pursuing an acting career, said her father changed her career path.
"My father said, 'I think you'll make more money singing than as an actress... And that was it," she said. "Obviously, he saw something. And it's sad that it takes away your childhood. If I had to do it all over again, would I go about it the same way? I would really have to think about that."
Joe Jackson, the patriarch and the driving force behind his children's success, has been accused by Michael and others of being an abusive stage father.
When asked by Roberts if her father was "abusive" or "old school," she said: "You have to keep in mind that I'm the baby...I think it's old school. And that may extrapolate into -- a -- being a little abusive. Do you understand what I'm saying?"
In a July 2009 interview with Chris Connelly, Joe Jackson addressed accusations that his children sacrificed a normal childhood for life on the stage. Joe Jackson denied allegations of beating Michael, but admitted to spanking as a form of physical discipline. He said he did not regret any part of Michael's upbringing.
"I was very young, very young. I can't remember the exact age, but very young, younger than ten, younger than nine. ...I remember when I had called him daddy, and he said, 'No, you call me Joseph, I'm Joseph to you.' Never said it again," she told Roberts. "...We called mother -- everybody called mother, mother. So I don't know, I don't know why. And I've never asked. I've never questioned it. It is what it is, and I just let it go. Joseph."
The Jackson children had a unique childhood. As devout Jehovah's witnesses, they did not celebrate birthdays or Christmas because of their beliefs.
"I would love to have experienced what it would be like to celebrate Christmas and birthdays. ...I had my first birthday party when I was 23 years old. And I'd never celebrated my birthday before then," she said. "You kind of feel like you missed something. But then again, you have to, to say to yourself, it's like a catch-22 -- well, how can you miss what you didn't have? You know? I -- we grew up pretty quickly."
Two days before her 43rd birthday was the last time Jackson saw Michael.
"We had a lot of fun, laughing. ...I was being silly, acting silly. And he was sitting in front of me and just cracking up, laughing at me," she said. "I was being loud. And he thought it was so funny. I was just being stupid, acting silly."
Watch Robin Robert's exclusive interview with Janet Jackson, "In the Spotlight," Wednesday, Nov. 18 at 10 p.m. ET.