9 Times Chelsea Handler Was Fearlessly Honest
EXPLAINING THE DIFFERENCE BETWEEN FEELING SEXY AND BEAUTIFUL
While reflecting on her 2016 with PEOPLE, Handler recalled the night she felt the most beautiful all year. "The other night I went to an event and I was wearing this Valentino dress. It was something I had never worn before that was beautiful," she said. "I was like, 'Oh my god, I look beautiful!' And I never, ever think that." The host went on to clarify that although she rarely identifies with the concept of beauty, she does often connect with the idea of being sexy: "I don't feel beautiful a lot but I feel sexy a lot. I think lots of things are sexy and I think confidence is sexy and I've never been short on that."
OPENING UP ABOUT HAVING ABORTIONS AS A TEENAGER
In a personal essay penned for Playboy's "Freedom Issue," Handler detailed the experience of having two abortions as the result of unprotected sex. "I just thought, 'Why not?' I can have a baby. Maybe I'll have twins and give them rhyming names," she wrote about discovering she was pregnant as a teen. "Of course, the idea that I would have a child and raise it by myself at that age, when I couldn't even find my way home at night, was ridiculous. My parents recognized that, so they acted like parents for one of the very first times in my life and took me to Planned Parenthood." Handler went on to express her gratitude for the legal rights that protected her choice. "Getting unintentionally pregnant more than once is irresponsible, but it's still necessary to make a thoughtful decision," she wrote. "We all make mistakes all the time. I happened to f--- up twice at the age of 16. I'm grateful that I came to my senses and was able to get an abortion legally without risking my health or bankrupting myself or my family."
REVEALING WHY SHE LEFT HER LATE-NIGHT GIG
Handler bid farewell to her late-night E! talk show Chelsea Lately after eight seasons, and she wasn't shy about the exhaustion with celebrity culture that motivated her decision. "To be quite honest I don't really care about Justin Bieber and I don't want to talk about him anymore. In order to make that happen I had to just stop doing my show," she told The Daily Mail about calling it quits. "I think if you participate in the celebrity world then you don't really have a choice but to be involved in the drama … You can sit around and complain about all that s--- and the Kardashians all day but if you're participating in it then what can you do? It really didn't feel great doing the show and the only way to sort things out was to extricate myself from the entire situation." Handler told the outlet she planned to drastically shift the focus of her future projects. "Now I want to do things differently. I want to talk to people who are going to educate me. Politicians, medical professionals and people with real human interest stories," she said. "I want to talk to people who have changed the course of the world. Inventors, invaders and people who have been doing exciting stuff."
BARING IT ALL ON INSTAGRAM
The unabashed star has made a habit of going au naturale on the Internet. Although the powers that be at Instagram have removed her topless photos a number of times, Handler won't stop stripping down to take on Donald Trump, celebrate America's Independence, wish her friends happy birthdays or for any other reason she sees fit.
DISCUSSING HER PARENTS' SHORTCOMINGS
Handler is not about sugarcoating childhood struggles. Speaking at the 2014 Gloria Awards gala, the comedian recalled the neglectful treatment she endured from her parents as a kid. "I grew up in New Jersey, and I was the youngest of six kids, and I had a father who was a used-car dealer and a mother who was a Mormon, and they slept a lot, kind of like cats. And they just never planned on having me, and I had five older brothers and sisters that were in college, and they said, 'Oh, you know, I guess you can raise yourself,' " she said according to Vanity Fair. "I heard kids around the neighborhood talking about nursery school," she continued. "I said, 'What's that? Nursery school sounds cool.' And I remember charging into my parents' bedroom, I'm like, 'What's everybody's talking about nursery school? Am I going? Am I going?' They were, like, 'No, no.' Meanwhile, I was still in diapers, because they hadn't bothered to potty train me. I was five. I'm like, 'And why am I wearing a diaper?' " Handler says her parents told her she would have to wait until kindergarten to start her schooling because it was in walking distance from her house. "They were, like, 'At least you can get yourself there, we don't have to be responsible for you.' And they were so not participating in my childhood."
SPEAKING UP ABOUT SELF-DOUBT
She may seem unflinchingly confident, but Handler revealed to PEOPLE that even she experiences her fair share of anxieties. "There are times I felt insecure or not sure, I'm unsure of myself, or I get nervous, but nerves are good," Handler began. "I try and embrace all those things. I try and embrace the times where I'm not sure of myself or I'm like, 'Is this going to work? Is this going to land?' Every time I had a book come out, I'm like, 'Is it going to be number one?' It's like, who gives a s--- if it's number one? You have five books … I don't think I'm a good host. I'm not a good host. I'm terrible at hosting. That's my problem. I can talk and have interviews, but I'm not a host in that sense."
TAKING ON SEXISM
After she was reduced to a mere parenthetical mention in a New York Times piece about Jimmy Fallon taking over the Tonight Show, Handler wrote an essay for The Huffington Post in which she unpacked the sexist implications of the article. "I obviously didn't expect or want to be a focal point of the piece," she wrote. "What bothered me was that when I was listed in a paragraph with the late-night hosts, I was the only name put in parentheses. Mr. Carter wrote, '(The only female host in late-night is Chelsea Handler, 38, on E!).' " Handler explained that she didn't want to be "inconsequential" nor "lauded" based on her status as one of the few women in a "traditionally male field." "I only want to be acknowledged for having worked hard to build an equally significant audience and fan base to those of my peers," she wrote. "I believe the success of any woman should never be qualified by her gender."
SHARING HER FAVORITE THINGS ABOUT ADULTHOOD
Handler brazenly discussed her extracurricular activities during an interview with The Daily Telegraph. "I don't live in regret," she proclaimed. "I have done a million embarrassing things; I've been at parties where I've drunk too much and made a fool out of myself. But it's pointless, in my opinion, to look back and have a shame spiral." Later, the actress explained that having her own home gives her the freedom she always craved. "Now that I'm an adult, I get to have people over to my house whenever. The other night my business manager came by at 12 p.m. We smoked a joint and played ping-pong for two hours and then he left. I thought, 'This is what I always hoped being an adult would be like.' "
TALKING ABOUT HER BROTHER'S DEATH
When she was just 9 years old, Handler lost her eldest sibling Chet, who died after falling from a cliff in Jackson Hole, Wyoming. "Seeing your parents fall apart is really rough," she told PEOPLE about the tragedy. "I wouldn't wish it on anybody … As hard as it was for me or for my brothers or sisters – [how did it feel] for my parents to have your own child in danger in that way? And then you can't protect them and you couldn't save them?" Handler believes the horrible loss eventually brought her family closer together. "In hindsight it really kept us as a tight-knit group, because it was so tragic and awful," she said. "Ultimately, it was kind of a beautiful gift because we all value each other so much."