Chelsea Handler
(6 of 7)
What is astonishing about watching Handler interact with her fans is that the more she insults them--"You're a mess. Look at you. I can't believe they let you in" is a typical interaction--the more they seem to like her. She's not kind, but she's consistent.
"There's no difference between public Chelsea and private Chelsea," says Tom Brunelle, executive producer and head writer of Chelsea Lately and co-president of Handler's Borderline Amazing Productions. "What you see on TV, in the books, that's what she is. So there's no danger of her misstepping, of her fans turning on her."
That long-term relationship with her fans--it is easy to envision them aging with her as she goes through all of life's passages with her typical rigorous honesty--is what makes Handler's continued presence on late-night TV so potentially lucrative. She's eager to move past her current focus on pop culture into a broader format so she can take on politics and current events. She has ruled out moving to daytime--she's too risqu for the View crowd--and while she has been beating Conan O'Brien in audience share, she isn't sure she wants to adopt a more straightforward late-night format. "She's the first female who has made it in late night," says Brunelle. "So we have a lot of options."
That night in Portland, early in her set, Handler relates an anecdote about how she likes short, chunky children. As soon as they grow up and "lean out," she finds them less endearing. She is drawn to one of her nieces in particular: Seneca, a chubby little girl with a lisp, whom she likes to wrestle and cuddle. To bribe Seneca to allow her to roughhouse with her, Handler gives her little fun-size Snickers bars, which she also adores for their chunkiness. One evening, as they were playing their game, Seneca fell over, her sweatpants slipped down, and then Chelsea's sister--Seneca's mother--walked in. "Only I would get caught with a chocolate bar three inches from a child's rear." Only she doesn't say rear.
From where we are watching backstage, comedian Josh Wolf turns to me and says, "Only Chelsea could make that joke work."
Handler recently bought a house in Bel Air, Calif., paying $5 million in cash for a gated estate where she lives with her brother Roy and two lesbians who divide their time between Dallas and Los Angeles. (Handler likes a big, noisy household.) She's put a few million more into decorating and remodeling the house, and on a summer afternoon, she points out the hill atop which she will build her gym; the eaves of the house, which she will remove and replace with Brazilian ipe wood; the dining table made from planks recovered from the piers of Venice. She shows photos of new chairs she is considering for the den. It will cost many thousands of dollars to replace older, very beautiful chairs that also cost many thousands of dollars.