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“I've always been, you know, good at oversharing,” Chelsea Handler tells me. It was said in jest, but she's right. Handler is really good at it. In a world that encourages people to reveal every intimate detail of their life on social media, she is exceptionally fearless. (A recent Instagram favorite of mine: the time she wore two surgical masks over her boobs with the caption “Wear a mask.”)
It's a skill that's led Handler to six books on the New York Times best-seller list, multiple talk shows, a Netflix documentary series, and a spot on Time magazine's 100 most influential people list. Which is why it was surprising that Handler, someone so accustomed to oversharing and overcommitting, actively decided to take a step back when it came to her stand-up career.
“I didn't want to do stand-up until I had something more important to say than what I had been saying,” she explains. That time has come: Her first special in six years, Evolution, is now streaming on HBOMax. Touching on love, loss, and Handler's first foray into therapy, Evolution is a journey of self-discovering. “Going to therapy and all the humiliating things you find out about yourself, it's two steps forward and one step back,” she says. “You think you're killing it after you meditate for 20 minutes, and then you get into a huge screaming match with a parking lot attendant. It's just a hot mess.”
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The step back from stand-up comedy did more than inspire a new special for Handler. "Before, I used to do so many things,” she says. “I would be on tour while I was filming my show, and I'd be writing a book and then promoting it. I burned the candle at both ends, and I felt like the integrity of my work wasn't where it could be.”
Now she prefers focusing on one thing at a time. And what's next? The election, of course—she even recently purchased a new ski chalet in Canada…just in case. More on that, plus what else Handler is buying these days, in our latest installment of Your Fave's Faves.
My favorite chocolates in the world are by Tobi Tobin. I have a box that my assistant hides in the house and doesn't tell me where it is until I ask him three times. So sometimes I'll text him and go, “Where are the chocolates?” And he will say, “Do you really want them?” And then I'll be like, “No, you're right.” Because I can't just eat one—I'll eat five, and they've got to at least be like 1,000 calories per chocolate. I have those when things are really dire.
I love jumpsuits right now. I wear my favorite jumpsuit by Apiece Apart in my stand-up special. Anytime I put on a jumpsuit, I just have a little bit more bounce in my step. I don't know how to explain it. With a cute pair of sneakers, it's my favorite uniform.
I love beverages. I could survive on liquid alone. My fridge looks like Sleeping With the Enemy because I have every flavor of La Croix, every flavor of Zevia, and then there's orange juice with half the sugar and Minute Maid sugar-free lemonade.
Right now my favorite app is Raya because I'm trying to get some action. It's very circular—you go through the same group of people, like, every six months. But it's been so long in this pandemic that I'm like, “Listen, I need to make sure my body still works.” So I'm trying to get something going.
Caste by Isabel Wilkerson is so important for every single person to read because it is gut-wrenching. Our responsibility as human beings is to understand the experience of others, no matter how unpleasant they may be. It's really important for us to be reading books like that, and she's an incredible writer. The book will change you.
My favorite pants to wear right now when I'm at home are my Pour Les Femme pajamas. Robin Wright is a friend of mine, and she was over here last night and brought me another pair. They are the softest! I never used to wear pajamas—I used to sleep in my bra and underwear—but she came out with these and now I have, like, 15 different pairs of them. They're so thin and light and feel incredible. I wear them all the time.
I bought a ski chalet in Whistler, Canada. I bought it partly out of fear because of the election. Just in case, so I have a backup place to go ski and pretend that, you know, this isn't happening.
My foam roller is my self-care because I had a herniated disc this summer, and that has been my recovery. I have the OPTP Axis roller, and I roll out every morning for about 45 minutes. I'm going to commit to doing that for the foreseeable future.
Put ice underneath your eyes if you've had a rough night and you're puffy. It's good. That helps, but also you can use an ice-cold spoon and put it onto your upper lid and underneath your eyes.
I really like these leggings by this brand called Graced by Grit. My sister actually turned me on to them. They're really good workout pants, so I wear them a lot. Plus, I like anything with the word grit in it.
Because I have big boobs, it's not good for me when they add too much padding to the cup. I just look bigger. So I like the minimal amount of padding in a bra. I prefer no padding at all, but sometimes that can look funky. Natori makes my favorite bra—I have about 14 of them. [Editor’s note: Natori bras are a fave among the Glamour staff too!]
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I'm pretty a big proponent of cannabis in your life to help everything go a little bit more smoothly and to help make everybody a little bit less annoying. I'm always handing out cannabis because I can tell just by talking to someone and assessing their body composition what they're going to thrive on, whether it be a chocolate-covered blueberry, or a gummy, or if they're going to do better on a one-and-a-half-milligram microdose. The chocolate-covered blueberries are my favorite. The great thing about cannabis now is that it's all labeled. You know what you're taking, and it doesn't have to be about being blotto. It's just about sanding down the edges a little bit, taking the load off a little bit. Sometimes it's imperceptible, but you just feel slightly more relaxed. And that's the point.
Anna Moeslein is the senior entertainment editor at Glamour.
