HANDLER LAUGHINGLY says her own work ethic—“whether you like me or not, you can’t deny I work my ass off”—comes from “watching my parents have the opposite! They never worked, and I just couldn’t believe their lack of planning. I didn’t ever want to be in that situation. I never wanted to worry about paying the phone bill or having something shut off. We were never starving—we lived in an upper-middle-class neighborhood, and we had a summer home on Martha’s Vineyard—but my parents had no financial plans. They had no savings. And I knew from watching them that that could never be me.”

Freewheeling finances aside, the Handlers proved to be supportive, nurturing parents, providing a firm anchor for their close-knit family. “Growing up,” she says, “my parents were really, really loving. They were always there. In fact, my sister’s best friend in college did a sociology thesis because she thought our family dynamic was so interesting. She interviewed all six of us kids and asked who we thought the favorite of the family was, and each child said themselves!
“What I’ve realized, especially through my relationships with men,” she continues, “is that as ridiculous as they were, my parents instilled in me so much self-reliance and self-confidence. I’ve always been sure about myself; I always knew I would do the right thing whether anyone was watching me or not.” As illustration, she retells a story she first recounted in her book, Chelsea Chelsea Bang Bang, about visiting a 15-year-old neighbor’s house when she was eight. “He pulled his pants down and said, ‘You want to play a game?’ I looked at him, kicked him in the balls and ran home. My parents were both in the kitchen, and when I told them, my dad said, ‘Well, good. We never have to worry about you. No man is going to take advantage of you.’ ”

THERE WAS one event, however, that shook the feisty, buoyant Handler clan to its core: In 1984, Chelsea’s older brother Chet died in a hiking accident at age 22. The comedian, then nine, retreated into her own private world. “I was shut down because I didn’t want to cry in front of anyone,” she has said. “That’s very unhealthy and took a long time to get over.” But ultimately, she said, she came to terms with his death, and the family grew even closer.

After a high school career mostly distinguished by her appearances in beauty pageants, and a brief stint at a community college, Handler moved to L.A. at 19, hoping to become an actress. Two years later, after telling a DUI story to a class of fellow traffic offenders and cracking them up, she decided to try stand-up in comedy clubs.

No surprise, given her Handler confidence, that she expected to become an “it” girl. The surprise is that she did: Her work in L.A. stirred up such a buzz that at age 24 she landed a spot at the prestigious Montreal Comedy Festival. And then? Her voice goes quiet. “It was one of the worst nights of my life. I bombed terribly. I wasn’t seasoned enough to be in the room I was in. Afterward, I sat alone in the bar like a leper and then stayed up all night in Zach Galifianakis’s room crying. But you can’t quit because it’s going badly. It’s like Mitt Romney singing ‘The Star-Spangled Banner’: You just have to keep going and going and going and going.”

Through these tough times, her parents and siblings kept rooting for her, as they always had. “My mom [who died of cancer in 2006] was amazing,” Handler says, her face softening. “She was always taking me aside, telling me why I was different, why I was special. And when I grew up and spoke to my friends from high school, I learned she did the same thing with each of them! She had a real serious empathy that she passed on to me. Even though I make fun of so many people, it’s done in the vein of the stupidity and nonsense of it. It’s not mean-spirited. It’s supposed to be light. It’s supposed to be silly.”