Chelsea Handler has made a career out of saying what everyone else is too polite – or too sober – to say. With multiple New York Times bestsellers, three acclaimed Netflix specials, and a voice that’s equal parts razor-sharp and deeply human, she’s turned radical honesty into an art form. Now, at fifty, she’s doubling down on her signature blend of humor and hustle – recently publishing a bold essay collection (I’ll Have What She’s Having, Random House Publishing Group), releasing another special (Chelsea Handler: The Feeling, filmed in her native New Jersey), and hitting the road with a brand new tour. From Chelsea Lately, her late-night comedy talk show that ran from 2007 to 2014, to her current podcast, Dear Chelsea, Handler has evolved from provocateur to introspective storyteller, still wielding her humor as a kind of truth serum. And while her passport may be full and her schedule packed, Martha’s Vineyard remains the place that grounds her, the summer backdrop of some of her sweetest memories. She recently chatted with Martha’s Vineyard Magazine to discuss why, no matter how far she goes, the Island still has her heart. An edited transcript follows.
Martha’s Vineyard Magazine: This year is shaping up as a defining year for you. You have a new book, new special, new tour, your own line of ready-to-drink vodka cocktails, and you turned fifty in February! Between creating, performing, and publishing, it seems like you’ve been in constant motion. Do you thrive at that kind of pace?
Chelsea Handler: Yes, I like to go hard and then play hard. I work really hard for a few months, and then I take a month off. My schedule has been crazy, and that’s just the way I wanted my life to be. So, it’s perfect.
MVM: Your newest book, I’ll Have What She’s Having, is a series of comedic essays about becoming the woman you always wanted to be. Can you describe that ideal woman you envisioned as a young girl?
CH: Independent is the number one priority or aspiration. Fierce, determined, and strong. I feel like I’ve come into my own in many of those areas, and while all those things are never permanent, they are recurring themes in my life.
MVM: Tell me about the title, which nods to the classic When Harry Met Sally scene.
CH: My book editor came up with the title. She said, “I think we have to call it I’ll Have What She’s Having.” I thought, that sounds a little self-aggrandizing. And she said, “No, that’s how you leave feeling – like, I want more of that in my life.” I thought that was a nice way to extend the message, which is what I wanted to instill in all women and all people. I like to inject them with a little of my confidence, with a little of my self-esteem and self-belief. The response from the book has been just that – people feeling empowered, motivated, having a little bit more of a push and belief in their own power to make the changes in their lives to achieve real happiness.
MVM: Up next is The High and Mighty Tour. Is there a central idea or feeling you want audiences to leave with?
CH: The High and Mighty Tour is my injection of laughter into this world we are living in currently, to give everyone a reprieve from the backdrop of the ugliness of the political landscape, and to just provide everybody with some relief and joyfulness. It’s a whole new hour that I wrote after my last special came out, and I’ve been having a lot of fun. It’s a lot of family stuff, a lot about editing some family members that I no longer need to be vacationing with every year. It’s an ode to microdosing. I love microdosing, and in this world, we need as much help as we can get. It’s a bunch of my personal stories that I haven’t shared yet on stage.
MVM: You’ve been a part of so many mediums: books, TV shows, podcasts, magazine columns. What keeps you coming back to live touring?
CH: Being face to face with people is really where it’s at. On my podcast Dear Chelsea, I get to talk to real people, and that’s one of the things I love so much about my career – I am accessible to everyone, and while I have a rarefied life, I’m not unrelatable. I’m honest about all the good stuff and the bad stuff, my shortcomings and my strengths. There’s nothing that gives me more joy than looking out into a crowd and seeing two strangers next to each other, bumping shoulders with laughter. I love that, and I love being a purveyor of that.
MVM: You mentioned the bad stuff. Early on in your career, people loved to label you “wild child,” “fearless truthteller,” and even “rude” and “crude.” Did those epithets feel accurate to you back then? What words would you use to describe yourself now?
CH: No, I never liked being called crass or crude. I never saw myself that way. I understand now how I came across that way, but there’s also this kind of “What is true for men is not always true for women.” You can be opinionated, loud, and confident as a man and nobody calls you any of those things. I think of myself as a fine wine, even though I’m not a big wine drinker. I’ve really matured and I’ve become more refined over the years. But I’ll always say what I feel like saying, and I am confident and I have earned the right to be. I’ve never really heard a man be called crass, ever.
MVM: More and more young people say they are anxious about the future: climate change, politics, AI taking over. They’re also famously drinking less, partying less, and supposedly having less sex. If you could give them one Chelsea Handler–style pep talk, what would you say?
CH: Well, I mean I’m not really a fan of no sex and no drinking. I am a fan of really going for it, you know what I mean? Abstinence is not a policy of mine. I live in Los Angeles, and so many people have quit drinking after COVID. I guess people overdid it during COVID. I did the opposite. I stopped drinking for the first three months of COVID because I was alone in my house and I thought…that sounds depressing. So, I experimented with other fun things like mushrooms and LSD.
But yes, I just think life is for the taking; we’ve got to get after it. This is the only life that we get, in my belief system. I’ve been having a really good time, and fifty is kind of like this cement block of like: you’ve done it, you’re legitimate. I don’t have imposter syndrome anymore. I’ve been very lucky, I’ve been very fortunate, and I’ve coupled that with making sure I work my ass off. I am proud of my hustle, and I am proud of where it’s gotten me and I’m proud to continue to hustle. I don’t expect anything to fall out of the sky.
MVM: Let’s talk about Martha’s Vineyard, where you’ve spent summers since childhood. What’s the first memory that comes back to you when you think of those early Vineyard days?
CH: Edgartown, Katama Bay, Mad Martha’s, the docks in Edgartown, fried clams, Giordano’s, going to the Flying Horses and walking up [Circuit Avenue] in Oak Bluffs, just all of the good stuff. South Beach, the Quarterdeck. That’s where I got my fried clams. My mother and I would eat fried clams at the Quarterdeck in those little white boxes, the little half-pint boxes. And to this day, there is no sweeter memory than eating fried clams on the dock in Edgartown.
Martha’s Vineyard is where I had my first lemonade stand – my first hard lemonade stand when I was ten. I had a hard lemonade stand on Katama Road, down the street from my house in Katama. It was also where I had my first terrible bicycle accident. I would bike into Edgartown every day and then I would go to the deli on Main Street in Edgartown and get a bagel with butter and a Twix bar and a Sprite. And then I would go and sit at the park right next to that deli and I just loved the phantasmagoria of flavors. I would take a bite of my bagel, a bite of my Twix, and then a drink of Sprite and I was like...Ahhh.
MVM: You mentioned your first lemonade stand was on Martha’s Vineyard. It could be said that the Island inspired your partnership with Owl’s Brew and the line you created of ready-to-drink vodka lemonade cocktails. Would you say you’ve always been an entrepreneur?
CH: Yes. Once I took a look at my parents’ non-existent bank account, I realized that I was in charge of my future, and that they were going to be of no help whatsoever.
MVM: How much time do you spend on the Island now?
CH: We sold our house there about ten years ago. And since then, we started coming there in the summers. I would just rent a house for my family every summer. And that started to get on my nerves because there’s twenty people in my family and they’ve all married people and I came to the realization when I turned fifty that I don’t really have to vacation with my brothers’ and sisters’ spouses anymore. That’s not my problem. That’s their problem. I’ll always vacation with their kids, my nieces and nephews, but I feel like I have earned the right to navigate with who I want.
MVM: What do you like to do when you’re here now?
CH: Edgartown is really the town for me because that’s where I grew up. I consider that my home. I like to go to the Navigator [now the Atlantic], or to that big hotel that my sister got married in.
MVM: The Harbor View Hotel?
CH: Yeah, I like the Harbor View. I also like the Harborside. I like that whole walk with all the captains’ houses. We always spend time in Edgartown, and whenever we rent, we rent in Edgartown.
MVM: And what do you do for fun?
CH: We go to the beach. We always jump off the bridge. It’s pretty much the same stuff I did as a child, except probably more drinking. I also always do Pilates with Sherry Sidoti. She’s our Pilates instructor when I’m there. She comes over every morning around 9 or 10 for family Pilates.
And then I have friends on the Vineyard. I always get to see them. Amy Schumer, Seth Myers. A lot of LA friends, work friends, industry friends are there too. And then I have family friends. Longtime family friends that we always visit with when we’re there.
MVM: The Vineyard is known for fostering multigenerational traditions. Talk to me about the role that the Vineyard plays in your family life.
CH: I feel like the Vineyard represents my happiest childhood memories. Everything good happened on the Vineyard. I remember hitchhiking all the time, walking around barefoot in stores and down the street in Edgartown. I grew up in an era where you could hitchhike as a ten-year-old kid, and you could walk around barefoot and we would pick up hitchhikers all the time. My brothers would always pick up cute young girls hitchhiking and then we would take them to the beach and they would make me do really cute things. They would be like, “Go into the water and act like you’re drowning. We’re going to come and save you so that girl can see us.”
Our house was right on Katama Bay so we would go down to the dock and fish. My brothers were always fishing. We had a little sailboat, and my brother would take us out and tip us over. Every time we went out, he would tip us out on the bay. Once they convinced me that there was quicksand down by the beach on Katama Bay. So there was an area that I never went to because I was convinced it was quicksand, which I later found out was obviously a lie and something out of The Princess Bride. But even the boat rides from Woods Hole were so emblematic of the fun that we were going to have.
MVM: Has the Vineyard influenced you in other ways? Has it inspired any jokes, perhaps, or hot political takes?
CH: It’s definitely part of the fabric of my life. I think in all of my books I mention Martha’s Vineyard. It’s part of my DNA. When people say, “Oh my gosh, you don’t love the Hamptons?” I’m like, “Don’t talk to me about the Hamptons! I’m from Martha’s Vineyard, where you don’t wear makeup and you don’t wear heels.”
