"Well, I didn't really have a choice," she said. "I was independent because my parents were over it. I was the sixth kid and they were, like, done with setting up playdates. It made me feel like a total outcast, because my parents just refused to participate in my childhood."
"There's a thing called helicopter parenting. My parents were like ceiling fan parents. They'd be on a little bit and then just turn off: 'We don't work anymore, we're in the Bahamas.'"
At the age of 19, Chelsea left her family to pursue an acting career in Los Angeles.
"I wanted people to know who I was. Even if it's not for everyone, I have a point of view that's different, and I was going to prove it to everyone. I just think I wanted to be famous."
She waited tables and started doing standup. TV shows like "Girls Behaving Badly" soon followed, and then she broke through with a book about her one-night stands. Fans were smitten.
When we met her on tour in Detroit, she spent most of her time off-stage signing books -- more than 500 in the space of a few hours. ("Make sure the book you have is my book, though!")
"I like to go on tour because I like to meet my fans. I like them to see me face-to-face, putting in the effort, putting in the time, not coasting on my laurels. And being on stage in front of that many people who have paid money to see you is a responsibility."
And what they're paying for is a 39-year-old single woman who makes fun of everyone, especially herself -- a woman who wrote a book called "Are You There, Vodka? It's Me, Chelsea."
But is she really that mean? Or that drunk?
"You know, on my tour, when I'm doing stand-up, people send drinks up on the stage all the time, and if I don't drink it, they're really upset. Or if I have a cup and it's clearly water, like, I always put it in a red plastic cup or a glass, because people want to think it's vodka when it's not necessarily vodka."
Smith asked, "How much do you really drink a day?"
"A day? Not as much as people think I drink at all. Yes, I drink. I don't drink every day. I'm not hammered every night. Hardly."
"At the same time, you have this empire. So when you joke about being a functioning alcoholic, you're not really?"
"No. I wouldn't call myself an alcohol -- I mean, I could be a functioning alcoholic. I'm sure a lot of people would say that about me. I may be. I don't think I'm an alcoholic. But I mean, most alcoholics don't think that, do they?"
And Chelsea Handler functions well enough to earn a reported more than $20 million a year from TV, standup comedy and book sales.
"So what do you think you learned about money, now that you have quite a bit of it?" Smith asked.
"To throw it away," Handler replied. "I have no respect for it. I give everyone -- yeah! I don't care about money. I mean, if somebody needs a car, I have no problem buying them a car."