Drew Barrymore could do anything she wants for her 50th birthday: an epic, glamorous party, wall-to-wall with A-list friends; an indulgent getaway in an exotic paradise or perhaps a chi-chi private dining event at an exclusive restaurant, wearing something expensive and fabulous.
But no: The superstar actress, talk show host and businesswoman instead plans to celebrate the milestone on February 22 in her happy place: bed! Yup, in typical Drew style, she’s eschewing the celebrity norm and following her heart: She’s throwing a sleepover, and her daughters, Olive, 12, and Frankie, 10, will be right there, snuggling up with their mom and probably leaving crumbs on the sheets.
“We’re the three sardines, and we’ll get into our can,” laughs Barrymore. “I’ve always spent the night with them on my birthday and their birthdays. We have a tradition, so I’m doing a night or two of sleepovers leading up, and then I’m doing a sleepover with my daughters on my 50th. But the whole theme of the 50th birthday is sleepovers. Sleepovers should never go away.”
As one of Hollywood’s best-known child stars, winning over the world’s hearts in 1982’s E.T. at just 7 years old, Barrymore was working — and partying — hard when most of her peers were innocently attending sleepovers. So now, it’s only right that she should get to enjoy them whenever she wants. Plus, these days, Barrymore is a cozy homebody who admits to subscribing to JOMO — the joy of missing out — and has even instructed her friends to try and get her out of the house more (“I’m just very peaceful and content!” she says). Ultimately, when she’s not working, she loves nothing better than hunkering down with her tweens, who she coparents with ex-husband Will Kopelman.
But before all the fun starts, she’s kicking off the festivities by cozying up with another special guest: Us! Barrymore sees her landmark birthday as the perfect chance to look back on what she’s learned from the half-century behind her and share her findings with the fans who’ve rooted for her every step of the way.
And what an eventful half-century it’s been. From the chaotic early days growing up in Hollywood to her more focused and often emotionally painful 40s, the star’s done a heck of a lot of living. Over those five decades, she can count three marriages, two kids, dozens of hit movies as an actor, producer and director, 35 awards and one seriously huge hit of a talk show.
It’s largely thanks to her chatfest that she’s earned a reputation for being warm, open and touchy-feely — something we got to experience first-hand as she invited Us to scooch closer to her. “This is going to sound ridiculous, but you want to come sit over here?” she asked.“Let’s get comfy!”
It’s that irresistible, inimitable sparkle of Barrymore’s that’s helped her survive (and thrive) through mind-blowingly tough challenges. From rehab to divorce, she knows that the generation who grew up with her has always had her back and holds nothing but admiration for this powerhouse who’s reinvented herself time and time again.
Somehow, Barrymore has been through pretty much every ordinary and extraordinary situation that a person might encounter but miraculously came out of them all stronger and with a lot of lessons learned. Turning 50 is often a moment of reflection, but for Barrymore, it also feels like a celebration of everything she’s built. She’s embraced her past without being defined by it, taken risks that paid off (and, of course, some that didn’t) and found a way to grow in front of the world without losing her sense of playfulness, easing into midlife feeling happier and healthier than ever. “I don’t think I’ve ever known a happiness that I feel now,” she says, “and I just didn’t know I would ever get here.”
Despite all her ups and downs, Barrymore now says her toughest years are actually the ones she looks back on most affectionately. “You made me realize that my two most challenging decades (teens and 40s) were my absolute favorites,” she texts Us after the interview. “And how happy the revelation makes me.”
It’s the least we could do to honor 50 years of a star whose quirky charm has all of Us wishing she was our BFF. Since she won’t be toasting with a drink (she’s been sober since 2019), celebrating with one of the cozy, open-hearted chats she’s so good at feels like the perfect way to indulge — plus lots of cake and flowers, of course…
Drew’s First Ten Years
Born in 1975 in the very adult and bohemian environment of West Hollywood and raised by a single mom, Jaid (she did eventually reconnect with her dad, actor John Barrymore, before his death in 2004), Barrymore wasn’t even a year old when she started in showbiz, appearing in commercials and, later, movies. It’s the decade that made her a star — but also put her on a troubled path where it felt like nobody was looking out for her. “I don’t think of it as the magic of childhood,” she reflects. “I don’t think I know what childhood is like, and I think that’s what made me so nervous when I became a parent.”
At first, Barrymore romanticized her unconventional upbringing. “My mom had a very colorful cast of characters coming through,” she recalls. “It wasn’t as safe as it should have been — but when I was younger, it was more whimsical. Not feeling like I had a childhood has nothing to do with feeling robbed of [one]. It just wasn’t your garden-variety youthful childhood, but I never feel upset about that.”
Shockingly, Barrymore says she started going to clubs aged 7, drinking alcohol at 9 and using cocaine at 12 — because nobody ever told her she couldn’t. “The whole concept of ‘no’ made me really rebellious,” she says. “As if it didn’t apply to me. ‘No’ made me angry, but it turns out ‘no’ is essential and has incredible benefits. It can make you feel a lot more safe and and cared for, even if you hate it at the time. It means someone or something is holding you.”
One of the few people who did look out for Barrymore was director Steven Spielberg, following the starring role in E.T. that made her famous. “Steven was like a dad,” she says. “I was getting an opportunity to meet a safe male who I looked up to and admired so much. He was very parental with me. He felt very protective of me, and I felt that from him, and it felt so good to get that care.”
Despite everything she went through, and her choice to be emancipated from Jaid in her teens, Barrymore now has a relationship with her mom, crediting Jaid with passing on her love of books and talent for comedy. “I feel very grateful towards her,” she says. “I just wouldn’t have this life [without her]. But I don’t know if I applaud her. I thank her. We check in. We have a very nice rapport. We speak on holidays. I can pick up the phone and text her.”
But if Barrymore could give her younger self some advice? “Knowing what I know now?” she laughs. “Yeah, you’re f—ed.”
Drew’s Teens
Barrymore’s adolescence saw her image turn from adorable child star to troubled teen, seemingly overnight. At just 13, she entered rehab after struggling with substance abuse. At 14, she published her first memoir, Little Girl Lost, and, following her “divorce” from her parents, worked in a coffee shop as she attempted to navigate adulthood. “After the institution, I felt some of the happiest and freest I’ve ever felt in my whole life,” she says. “So it’s a very positive decade for me. That was also where I was like, I got to be f—ing accountable and responsible. I’ve got to own my s— if I have bad things happening to me. I did things nobody else did, and I just learned so much and had so much fun.”
Learning is a recurring theme for Barrymore. She often mentions that she never went to college but has compensated with a voracious hunger for knowledge — whether she’s gained it from reading, traveling or doing what she does best: talking to people. And that all started at Van Nuys Psychiatric Hospital. “What the institution taught me was that if you sit around and discuss things and you don’t sweep ’em under the carpet, it will get better,” she explains. “And that’s what the show is — based on that!”
One low point? In 1994, aged 19, she married Welsh-born bar owner Jeremy Thomas… but the union only lasted 19 days. She once referred to him as “the devil” in Rolling Stone. Today, that infamous quote makes her smile. “I kind of love my old self,” she laughs. “Now, I’d probably be a lot more diplomatic. God bless her — it’s funny how you can get more self-conscious as you get older! That was just a mistake… because we weren’t really a couple; we weren’t marrying for love.”
When Barrymore looks back on her teens, she sees a decade that, on paper, sounds like the toughest of her life but that she now regards as her best. That stereotyped wild child was actually escaping a painful childhood and embracing her freedom. “That totally encapsulates it,” she says. “I think, in my subconscious, I was like, ‘F— it. I didn’t have a childhood, so now I’m going to do whatever I want.’”
Drew’s 20s
It wasn’t until her 20s that Barrymore started scoring prominent roles again. The Wedding Singer, released in 1998 when she was 23, was a turning point. She also actively worked on her recovery from substance abuse, reunited with her father, John, plus met another parental figure who’s become a huge part of her life: producer Nancy Juvonen, cofounder of her production company, Flower Films.
One of their first success stories was Charlie’s Angels in 2000, and the pair have since become a formidable professional duo, which Barrymore puts down to their key differences. “[Nancy] was trapper-keeper binders, organizing, Post-its, index cards,” she says of Juvonen, who later married Barrymore’s Fever Pitch costar Jimmy Fallon. “She brought rigor. I had an infallible work ethic… we just went to work and we’d have the best time ever. In our meetings, I’d be the more artistic or emotional or expressive one, and she was the one who was more grounded and pragmatic and still had such an amazing ability to storytell, while I’m not the best pitcher.”
Barrymore’s 20s weren’t all hard work: she also had fun, spending much of her free time going to concerts and festivals — she was in a relationship with the Strokes’ Fabrizio Moretti for almost five years — and seeking out new kinds of thrills: skydiving, swimming with sharks, trekking and going on RV adventures. She also met her second husband, comedian Tom Green, on the set of Charlie’s Angels, but their marriage lasted just over a year. “We were just kids, and he’s a really wonderful human,” she says. “I think both of us felt bad that we tried something that didn’t work out. I just think the world of him’ he’s a good soul.”
Looking back, her 20s signaled several watershed moments for Barrymore, and while her romantic relationships were short-lived, she met her soulmate in Juvonen. “She’s the best thing that ever happened to my life before I had my kids,” says Barrymore. “And she knows that she’s the love of my life.”
Drew’s 30s
Like many women, Barrymore’s 30s had one big goal: motherhood. And it was a transformative charity trip working with children in Africa that made her realize this wasn’t only something she desired, but something she might actually be good at — which came as a shock after her own upbringing. “I was finding out who I was,” Barrymore says. “I was so happy to have a healing journey with kids; they were nice to me, and they didn’t know who I was. I think I thought of myself as toxic with kids; I just had no relationship with them. So this was the first time I had a relationship with kids, and I loved it.”
Finding the man who would make her a mother took a little while. After an on-off relationship with actor Justin Long, who she appeared with in He’s Just Not That Into You and Going the Distance, she got together with art consultant Kopelman in 2011. They married in 2012, the same year Olive was born, with Frankie coming along two years later.
From the outset, Barrymore was determined to give her girls a safe, secure childhood, far removed from her own wild start. “That’s what made me so nervous when I became a parent,” she admits. “[Children] are the great lessons, but they can do a number on your confidence. I didn’t really know what childhood was like but wanted so badly for my kids to have a childhood. I don’t know what anonymity looks like, what going to school regularly looks like. I don’t know about consistent bedtimes and rules. I never had any of that.”
As the girls approach adolescence, Barrymore tries to find the right balance. “They are who they are, and they’re their own people,” she explains. “I’m not desperate to impose upon them at all who they should be, but sometimes I feel it’s my responsibility to show them how to be and that there’s just no room for not being kind to people or gracious or grateful. If I had one battle to choose, it would just be that they’re kind, good, humble, grateful people and that they feel safe.”
Drew’s 40s
Barrymore’s 40s began with highs — she released her memoir Wildflower, which became a bestseller — and lows: In 2016, she and Kopelman divorced, which hit her hard. “I didn’t realize that I would find myself in a very personal space that felt as challenging as when I was 13,” she says. “I didn’t think that was going to come my way again. And it really threw me off my feet, and my girls gave me the ability to go, ‘It really isn’t about you anymore.’ There just came a time when I was like, alright, this is the most real thing: to be a good mom.”
Barrymore says she “lost sight” of how to cope. “I had to figure it out for the sake of my children. The good news is I did! If there was a ‘little girl lost,’ it was like ‘woman lost.’ And I just thought, being lost is not acceptable; you’ve got to find yourself.”
And so she did. One step was quitting alcohol at 44. “I had to stop,” she says. “I just don’t drink. That is poison for me. And when I stopped, there was so much work to do. For me, it was like, if I get rid of this, the real work can start.”
Out of the ashes of her marriage came a huge number of professional achievements: she launched her cosmetics brand, Flower Beauty, and, in 2020 — right in the thick of the pandemic — her talk show, The Drew Barrymore Show. It’s billed as “optimism TV” — and that is so Drew. “I was so excited and grateful that I had something to try and build,” she says. “What a wonderful, intentional distraction and possibility that was. It was just such a wild time.”
The show was like a lifeline for Barrymore, who felt “so alone” following her divorce. “I knew that if I made it all about my kids, that was dangerous,” she says. “I needed to find my resources of stability and strength. I had them professionally and for my friends, but I didn’t have them for myself.”
The tail end of Barrymore’s 40s has been much happier. “Where I found myself was a place where I’ve never been so upset,” she reflects. “I’ve never been that down on myself. And it was a real wake-up call that this is no way to live. Things happen. You can get through them. Please do not be so lost and mean to yourself that you don’t know your way up. The revelation in the early 40s was not about alcohol or divorce. It was like, it’s f—ing game time to get my s— together and be the most solid person I can be.”
Now, she’s enjoying the stability of working in TV, being around for her girls and quietly dating as a single mom. “I’d love somebody who inspired me,” she says. “Who knows as much as I do or has worked on themselves as much as I have. I cannot go backwards.”
Although she’s “open” to a relationship, she’s perfectly happy single, saying, “I never feel like something’s missing.” Calmer and more content than ever, Barrymore tells Us, “I was so capable of having fun and experiencing joy, but I don’t know if I was happy. There’s such a big difference, and now I’m actually happy. This decade has truly helped me find ways into choosing happiness, and I have to choose it every day over and over again.”
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