Wit, Wisdom and Wellness

After years of groundbreaking success as a comic, talk show host, podcaster and bestselling author, Chelsea Handler has revitalized and prioritized touring nationwide, and on August 26 rocks East Hampton’s Clubhouse as part of her Little Big Bitch tour. Cristina Cuomo speaks with the political satirist about the importance of standing in truth, fighting the good fight and the healing power of humor.

CRISTINA CUOMO: I love that you are living your dream. I’m excited about your tour. Where did it all begin?

CHELSEA HANDLER: Livingston, New Jersey. I was born to a family that already had five children, making me the youngest. My parents were pretty wiped out—I guess would be the right way to describe their parenting—by the time I came along. I came out at a very early age with a mouth on me, very disgruntled by my upbringing. I couldn’t believe how disorganized and financially ill-prepared my parents were to be raising six children. I stepped into leadership mode at a very young age. I was large and in charge. Even at age 3 I was harassing my parents, asking them if I had a dowry, what was their plan, did they have a savings account. I was a terror from the moment I could use my mouth. My dad tried to calm me down by making me read big books. He just knew I was going to be trouble, so he made me read Anna Karenina, Tolstoy, Dostoevsky and Moby Dick when I was 7 and 8 years old. He thought that was going to quiet me down, but it just gave me more information to get back at them and go at them all the time about—he was a used car dealer, so he wasn’t the most honest, upright guy. My whole life I was on him like, “You can’t do that. You need to look people in the eye. You need to respect people.” I think I was born waving a women’s flag.

CC: Who was the big influence in your life?

CH: My brothers and sisters had the biggest influence on me. They championed me and loved me. When I was 8 and 9 years old, they were taking me to fraternity parties. My brother would be like, Go up and go off on that guy, he’s an idiot. I grew up very quickly, and my brothers and sisters will tell you that it’s been this way the whole time. There has been no change in personality, except for when I went to therapy when I was 40, and decided that I don’t need to attack everybody when I talk to them if I don’t like them. Also, if I don’t like them it’s not necessary to disclose that information right away. I tempered myself quite a bit, but I think that was a very valuable two years of my life, gaining the gift of self-awareness and recalibrating myself as a stand-up. It just gave me a new energy toward all of my creative endeavors, stand-up being one of them, because I had taken a six-year break. I came back and I did a special three years ago for HBO Max and then another one last year for Netflix. Now I’m just so into it in a way that I hadn’t been for a really long time. So, therapy is the gift that keeps on giving.

CC: I’m glad it helped you find your groove. What was a life lesson or experience that led you to be such a dependable friend and sibling, and to live instinctively?

CH: It’s funny that you use the word “dependable,” because if there is one word that I would want people to use to describe me, that would be it. Growing up, it was very important to me to be dependable not only for my friends but for people that I don’t know, people that are in need and people that you meet that are going time comparing yourself to other people, on Instagram and on social media. The only way to get to know yourself is to really spend time alone. A lot of people are scared of that. I know I was. I think meditation, being alone, writing, journaling, whatever you’re into you can’t ever do more of it. Nobody ever said, Oh, I started meditating and my life went to shit. Or, I started going to therapy and it went to shit. Getting as close as you can get to who you really are is only found by being with that person which is you, alone. I was very scared of doing that for a long time, But now I love it.

CC: Do you have a pet peeve?

CH: Oh yeah, like a million. Men’s toenails. Bare feet on through something. It could be a stranger. I just want to make sure people know, you’re safe with me, I’ve got your back. Especially for women and any group that I feel like is targeted or marginalized.

CC: What’s the best advice you’ve ever been given?

CH: It doesn’t matter how many people say no, you just need one person to say yes.

CC: I love that. What’s the most outrageous thing you’ve ever done?

CH: I dove off a sailboat in the middle of the Balearic Sea while I was on an edible, and swam 3 miles to the house we were renting to get away from my Russian sister-in-law.

CC: And clearly you survived it.

CH: Yeah, I’m now a strong swimmer after that.

CC: I know you’re a strong skier. I watched your bikini ski thing. That was hilarious but also very impressive and healthwise, smart, like a cold plunge. You’re such a forthright and unapologetic woman. How can we get more women who are always chasing confidence to be more like us?

CH: I think women really have to spend time with themselves alone and lessen the outside noise, spend less planes. That’s more than a pet peeve. I feel like that should be illegal or finable at the very minimum. Male jewelry. Room temperature water is a huge pet peeve of mine as well.

CC: Can you give us a glimpse into some subjects you will be covering on the Little Big Bitch tour?

CH: I talk a lot about my childhood antics. I started a lot of businesses when I was a little kid to try to split ties with my family, because I was looking to get my own place at around 8. I talk a lot about my origin story. Then I get into adulthood and talk about some of my close calls, close encounters that I’ve had with a lot of people that have been canceled. My sister has a theory that our dead mother is basically navigating my life from heaven and that I get out of close calls always at the last minute, not because of me and any intuition, but because my mother removes me from the situation.

CC: So, you’re a spiritualist if you’re communicating a little bit with your mom.

CH: Oh, yeah. I communicate with my mom more now that she’s dead than I did when she was alive probably.

CC: I love that. You’re a very learned woman. I don’t think most people would know that about you. What is something people don’t know about you other than that?

CH: Each week I read about four books. I have to read one section of everything—one nonfiction, one fiction, one historical and then one autobiographical.

CC: What do you want people to take away from four seasons of your podcast, Dear Chelsea?

CH: The podcast is just because I absorbed so much during therapy and I went to this incredible therapist, Dan Siegel, who’s written a series of books, and I ended up writing my last book about him and my experience. I just couldn’t wait to dish it back out and share it with everybody—for the people who can’t afford to spend going to stand for any of these draconian laws or rules. Voting is the most important thing you can do. So many young people are disgruntled because they don’t want to vote for an 82-year-old man, but it’s the choice between decency or indecency, and it’s the choice between everyone’s future. serious money on a psychiatrist. When I started Dear Chelsea I thought people were going to call up with questions about anal sex or whatever, but it turned into something very serious and very moving and profound. People call up with major life decisions and we’re able to steer them in the right direction ,or in the direction of taking a risk and believing in yourself. I think a lot of people are lacking the confidence to make them move, and they need a kick in the butt—a big sister who’s going to kick you in the butt.

CC: What’s your favorite medium as a political satirist?

CH: I did The Daily Show also this winter, one of the best outlets that I can have, because I digest the news and then regurgitate it back to everybody else—it’s my favorite thing to do. That is also a thing that I feel like I should be doing again, a late-night show.

CC: How does comedy foster positive behavior, and have you observed this healing power of comedy through your work?

CH: There’s a healing power in sitting next to a stranger at the Clubhouse in the Hamptons, and laughing hysterically with someone you’ve never met before. That’s definitely healing. My whole social media is a lot of serious issues but with comedy because it’s more easily digestible through that lens. Nobody wants to be yelled or screamed at. I used to do a lot of that. I don’t anymore. It’s light and it’s fun and it’s informative because I want people to be understanding of what’s at stake.

CC: What do you source your creative inspiration from?

CC: You really take deep dives in your podcast. It’s so educational on so many levels. You stand for a lot of important issues.

CH: It just feels like a death call for old white men who are losing power, so they are trying to strip away everybody else’s power in the process. I was listening to The Daily podcast yesterday about the women in Afghanistan and what they’ve had to endure, and I was just thinking they would love it in this country if they could do that to women. Taking away our reproductive rights is the first step in making that happen. I’m very hopeful that our future is bright, and that these young people that we have coming up are not

CH: I like to spend a lot of time traveling. After this I’m about to take a three-month break. My first show back I think at the Clubhouse. I did the first leg of my tour and I make sure I travel and see the world. I’m going to Africa, Portugal and London for Wimbledon. I’m going to Majorca for a month. I go and I travel and I make sure that I understand what’s happening in different parts of the world and I fill my brain up with something that I have to reflect on and turn into stand-up when I come back.

CC: One of our Purist premises is self-care. It’s about taking care of ourselves so we can better care for others. What are some of your go-to wellness rituals?

CH: Meditation every single morning. I have a hyperbaric chamber which sounds ludicrous, but it’s really helpful for jet lag, for sleep, for inflammation, for everything. I am very into wellness and taking care of myself. I’m on the road a lot so I’m constantly getting IVs wherever I go. I always get in my exercise first thing in the morning. I’m very early to rise. I get up around 6 every morning and I make sure I work out for about an hour. I hop in my chamber. I do my meditation. I write down 50 things I’m grateful for every morning.

CC: You are a wellness warrior indeed.

CH: Then I start my day so that I have a great attitude because I went through a time in my life where my attitude sucked and it showed and now it’s great, and it shows.