The comedy icon rings in half a century in her trademark fearless way.
Chelsea Handler Celebrates 50 Years: “There’s So Much Proof of Positivity in My Life”
Published on Mar. 14, 2025
Chelsea Handler has never been one to play it safe. Whether she’s pushing boundaries in comedy or trying ayahuasca for TV, she does things her way—with confidence, and her unapologetic self-deprecating humor.
Now, as she celebrates having turned 50 on February 25, the comedienne is once again hitting the slopes in a bikini (a birthday tradition of hers)—this time, not just for fun, but to set a Guinness World Record for the Largest Swimsuit Ski Run.
The event, in partnership with Gold Bond, isn’t just about making history—it’s also a reminder that the end of winter can be brutal on the skin. “I am a moisturizing lunatic when it comes to skiing and being outside,” Handler said. “This is the perfect dream partnership for me, it combines all of my favorite things: hydration, lubrication, and skiing.” Of course.
Between her book I’ll Have What She’s Having—which recently debuted at #1 on The New York Times bestseller list—a new Netflix special, and a Vegas residency, Handler has a packed schedule. But she insists she feels better now than she did in her twenties, crediting weight training, confidence, and therapy. “The irony is that I finally have the body I wanted when I was 20 that I have at 50 now!” she said.
Handler recently spoke with The Healthy by Reader’s Digest about her annual bikini ski tradition, what she’s learned from therapy, why White Lotus should call her, and why she feels hotter now than ever.
This interview has been edited for length and clarity.
The Healthy by Reader’s Digest: You’re partnering with Gold Bond to attempt a Guinness World Record for the Largest Swimsuit Ski Run. Your tradition of skiing in a bikini on your birthday has garnered much attention. What does this annual ritual signify for you?
Chelsea Handler: Initially it was just me. It just became less and less clothing, and then it just became more and more invigorating. The more clothes that came off, the more invigorating it became, and people were so stunned that I was able to ski in cold weather. I wanted everyone to understand how it’s so empowering. You don’t even feel cold when you’re skiing down a mountain in your bathing suit. You feel like a woman.
It became a tradition and then this year, since I was turning 50, I wanted to bring another group of women with me. So I got about 25 girls and we did it for my birthday, and it was such an epic day. And when I heard Gold Bond was doing this Guinness Book World record run with swimsuit, and this is co-ed, I was like, “I have to be a part of this because there’s no other celebrity that can ski like me and is willing to be in a bathing suit. I’m your ringleader.”
The Healthy: How fun!
Chelsea Handler: And I’m also a huge fan of Gold Bond because as a skier, the protection of your skin and the dry factor [is important] and I have very naturally dry skin. They have this healing hydrating cream for your body that I put on every day before I go skiing. And then at night I put all over my feet, my elbows, my knees, anywhere that becomes a dry area or has the potential. My philosophy about dry skin is you have to get ahead of it because once it gets too dry, it’s almost like you can’t catch up.
The Healthy: Are you an ice bath person, since you’re conditioned to the cold?
Chelsea Handler: I’m not into taking ice baths. That’s too cold. But I’ve done it. I’ve done cryo. But there’s something about skiing. Ice baths are shocking cold and it’s meant to [be]. But when you’re skiing in your bathing suit, you’re not going to do it for five hours in a row, but there is nothing more exhilarating and it’s so adrenaline-inducing that you do not feel cold. It’s like a jolt.
The Healthy: At 50, you exude confidence and vitality.
Chelsea Handler: I mean, I’ve always had a lot of confidence. I think it was just a little bit misplaced and false when I was a lot younger. I think you’re born with confidence or not, but you can always cultivate it. I feel powerful about injecting other people with optimism, with confidence, especially our young people in this world. And my most recent book, which I just found out is number one on the New York Times list, is all about really helping people understand who they are, what your purpose is, and bracing yourself and really, really learning how to have a love affair with yourself. Forget about the partners, forget about all of that. Your relationship with yourself is really the most important relationship you’re going to have. Once that is solid, you can spread so much joy and love to so many other people. No one is going to believe in you until you really believe in you.
The Healthy: Along with your new book, I’ll Have What She’s Having, you also have an upcoming Netflix special, a Vegas residency. Do the accomplishments still feel as excited as they’ve always been for you?
Chelsea Handler: I mean, getting the call yesterday that I was number one on the list of the New York Times… I’ve gotten that call six times and it will never get old. I burst into tears. I understand you don’t have to be the best, the biggest, the number one. I have this different attitude about it, but it still feels great to find out that you do get it, that you do get the top spot. It feels very validating. It feels like I know what I’m doing. I’ve done this now six times. I don’t know how many people can say that. I’m enjoying the moment in the way that I enjoy all highs and all lows, knowing that these moments are fleeting. They don’t last forever. My job is just to be even about the whole thing and never get too high, never get too low, just be on solid footing.
The Healthy: We love your books—they’re just so funny! After decades in the business, what do you feel like has been your new take, that feels fresh to you?
Chelsea Handler: There’s no more feelings of uncertainty or self-consciousness. And there’s so much data now when you turn 50, there’s so much proof of positivity in my life. I’ve gotten myself this far. I’ve picked myself up from every heartbreak. I’ve picked myself up from every failure and I’ve succeeded, and I’m still succeeding. I’m no longer worried about the future; I’m not worried about the past. I’m so in the moment and feeling present and being present, which is a total practice, we all have to practice. That is the biggest supplier of joyfulness. When you can be in the present moment, you’re going to win. Even if that moment isn’t great, you’re going to win. If you’re paying attention and you’re not preoccupied with the past or the future.
The Healthy: We thought of you when we saw that this season of White Lotus has a famous, vivacious celebrity who took her friends on vacation. Do you watch it?
Chelsea Handler: Yes, of course. Leslie Bibb is a good friend of mine and she’s in that, so it’s funny you say that. White Lotus is obviously great. I would love to be on White Lotus. But I know I don’t think it was inspired by me. I think it was just inspired by female relationships.
The Healthy: You’ve been open about experimenting with different things, like psychedelics and their impact on your perspective. What has been the major impact of that experience and maybe other ones that have helped you get to this point?
Chelsea Handler: Just to see people, to really see people and take them in, not to judge people so much when they don’t have your value system or you disagree. It’s to really just take people in and understand that everyone is coming from a different place. You don’t have a shared experience with every single person. My childhood was not another person’s childhood. My trauma was not another person’s trauma. And to really just be patient and kind with people, and to show and demonstrate generosity of spirit and also to keep the vibes high. I’m a high-vibe person. I want people to have fun when I’m around. I mean, through therapy I’ve learned it’s not my responsibility, but I sure do love injecting people with a good time.
The Healthy: What’s been the biggest change you’ve noticed physically as you turn 50? And how do you plan to stay healthy through the demanding schedule of a Vegas residency?
Chelsea Handler: Well, actually, my Vegas residency is once a month. That’s perfect schedule for me because I would never be able to do a show seven nights a week. I would have no desire to do a show that many nights a week. I value my downtime as much as I value my work time and my hustle.
But the biggest change about my body, I mean, the irony is that I finally have the body I wanted when I was 20, that I have at 50 now. I understand how important weight training is, how important it’s to be strong rather than to be thin. And because of that, I have achieved both of those things. I tortured myself in my twenties and thirties with my weight and with my eating, starving myself, and this and that—all of the bad stuff that so many women are subjected to and so many women buy into. So to be so fit at this age and to know that I’m strong and capable and I’m a better skier than I’ve ever been, I want people to know every single day is an opportunity to get on the right track and change.
The Healthy: What is one self-care habit you refuse to skip?
Chelsea Handler: Sleep! I love sleep. I sleep. I mean, I could sleep for 10 hours a night easily, and if it’s less than six, then I am not down with that. I’m not somebody who can get by in a little sleep. I need my sleep.
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