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Most Beautiful 1990: Being named one of the World's Most Beautiful celebrities in 1990 came as something of a shock to Pfeiffer. the actress told PEOPLE. "It's the way my mouth sort of curls up, or my nose tilts up." Landing on the cover – again – nine years later, Pfeiffer told PEOPLE of her younger self, "I did nothing beauty-wise. People were horrified by how I treated my skin."
Now: The 58-year-old actress sees the upside to aging. "[Part] of feeling sexy is feeling comfortable in your own skin, and less inhibited," she told InStyle, "and that goes along with getting older."
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Most Beautiful 1992: "My face must have dropped in the last five years," joked the then 29-year-old beauty, who had just earned a Best Actress Oscar for The Silence of the Lambs and won raves for Little Man Tate, her directorial debut. "Suddenly I got bones that I never had before. Now I really enjoy putting care into my clothes, my makeup, my appearance."
Now: Fifty-four and a mom of two, the actress says she isn't likely to try cosmetic surgery to keep her looks in check. "For me, it's really a self-image thing," she told More magazine. "I'd rather have somebody go, 'Wow, that girl has a big nose,' than 'Wow, that girl has a bad nose job.'"
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Most Beautiful 1993: The 27-year-old supermodel was on a roll that year: She was the face of Revlon, had a hosting gig on MTV's House of Style and was married to future Sexiest Man Alive Richard Gere (he earned that distinction in 1999).
Now: In the decades following her Most Beautiful cover, Crawford got divorced, remarried and launched successful home furnishing, fashion and skincare lines. She also developed a good attitude about getting older. "I take care of myself, but I don't want to be obsessive," the 51-year-old mom of two told Allure. "I'm all for fighting the good fight, but I don't care how much you work out or how much cream you put on – things change."
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Most Beautiful 1994: When handed the title, the actress said, "Beauty is a very oddball subject to talk about in terms of yourself." Her Sleepless in Seattle costars happily did it for her, though, with Rosie O'Donnell calling her "completely adorable" and Tom Hanks saying she's a "formidable presence" and "not a little wisp of a blondie." Voted "cutest" by her classmates at her Connecticut high school, she told PEOPLE, "I've never thought of myself that way."
Now: Though she kept her résumé packed through the 1980s and '90s, Ryan retreated from the spotlight following her split from Dennis Quaid, moving to New York, scaling back on projects and interviews and quietly adopting a daughter, Daisy, in 2006, while raising her now-adult son Jack Quaid. The 55-year-old recently stepped back in front of the camera, though, for Ithaca, a World War II-era film she also directed and debuted at the Middleburg Film Festival in Virginia.
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Most Beautiful 1995: Back in the '90s, the Friends star admitted to being a facial product fanatic. "I have 150 cleansers in my bathroom," Cox said. But she was low-key about the rest of her beauty regimen. "I only have to do three things to look halfway decent: Curl my eyelashes, fill in my eyebrows and put some lipstick on," she shared.
Now: At 52, the actress, who has a daughter with ex David Arquette, has stopped her skincare experiments and sticks with a wash and moisturizer by Mila Moursi, her facialist. But, as she told Redbook, she also uses this trick: "I pour a little neroli or lavender oil onto a hot towel and use it to wipe off my makeup. It opens up my pores, and then my face cream sinks in better."
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Most Beautiful 2000: With her girl-next-door looks and laid-back charm, it's no surprise that the Georgia belle graced four World's Most Beautiful covers (1991, 2000, 2005 and 2010) – a PEOPLE record. In 1993, The New York Times gushed about the Pretty Woman star, writing, "Her skin is as clear as one of those High Sierra streams where the rare golden trout still swim."
Now: How does the actress, 49, keep her famous smile healthy and bright? With baking soda! In general, the busy mom of three has little time for a more complicated beauty routine. "I'm happy if I have on moisturizer and ChapStick," she told InStyle.
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Most Beautiful 2001: Zeta-Jones has made no secret that looking good takes effort. "I think beauty is a gift that you have to make the most of," she said. "I've worked hard at trying to look my best." She had a little help: night moisturizer. "Sometimes I look like a seal because I'm so lathered in the stuff."
Now: At 47, Zeta-Jones is still a stunner. She told Australian Vogue, "[and] with a little help from our friends, it makes it even better." Those "friends" include the honey and sugar she uses to moisturize and exfoliate her entire body. "You wash it off and your skin is gorgeous," she said.
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Most Beautiful 2002: "I was the plain one," proclaimed Kidman, talking about growing up with a younger brunette sister. By the time the Oscar winner graced PEOPLE's cover, she knew her porcelain skin was an asset. "Nicole won't even cross the road without a hat," said pal Naomi Watts. "She's really disciplined about that and it pays off. Her skin is like a perfect china cup."
Now: Happily married since 2006 to country star Keith Urban, with whom she has two girls, the 49-year-old actress still makes suncare a priority. "It is the worst thing in terms of aging," she told Marie Claire, "so I wear a lot of sunscreen, and I never go in the sun."
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Most Beautiful 2003: The woman who'd made history the year before as the first African-American to win the Best Actress Oscar (for Monster's Ball) described herself as "very imperfect but okay with my imperfections." When asked to name her apparent flaws, she said, "Where do I start? I would get a nose job" – plus "a boob lift."
Now: When does the 50-year-old mom of two think she looks her best? "I feel the most beautiful whenever I'm doing things that I love," she told PEOPLE. "I love work, I love being around children, I love reading."
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Most Beautiful 2006: When she was featured on PEOPLE's cover, Jolie had already distinguished herself as a humanitarian who regularly went on missions to developing countries, distributing food to the poor, even sleeping on frozen ground after a hard day's work. Her beauty regimen was just as un-diva-like: a little face powder, mascara and a dab of Vaseline on her lips.
Now: Jolie, 41, has continued traveling the world as a special envoy of the United Nations High Commissioner for Refugees. "I am a proud American and I am an internationalist," the actress said during a March 2017 speech for the UNHCR. "I believe anyone committed to human rights is. It means seeing the world with a sense of fairness and humility and recognizing our own humanity in the struggles of others." In September, Jolie will head to England to teach a Master's class at the London School of Economics' Centre for Women, Peace and Security.
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Most Beautiful 2007: Saying she felt most beautiful "right after I've worked out and I'm sweating all over the place," the former child star described the happy results: "I feel like I've changed the shape of my body temporarily into something more flexible and strong."
Now: The actress, 42, who’s mom to daughters Olive, 4, and Frankie, 2, has added another title to her credits: businesswoman. In 2013 she started a cosmetics line called Flower and spends time doling out beauty tips.
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Most Beautiful 2008: The natural beauty confessed to PEOPLE at the time, "I don't even remember the last time I got a manicure." Her priority: spending free time with then-5-year-old son Ryder rather than in a salon. Still, when she did get a facial or leg waxing, "I always think, 'I should do this more often.'"
Now: At 37, the mom of two (she welcomed second son Bingham in 2011) tells Self, "Some of my girlfriends get lasers and things, and I say, go for it, babe. It's important for women to find confidence. Whatever makes people happy."
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Most Beautiful 2009: After being diagnosed with breast cancer and undergoing a double mastectomy a year earlier, the actress was learning to appreciate her new body: "I don't have to wear a bra!" she said. "And the gals look good in tank tops." Helping her heal: boyfriend Martyn LeNoble, who made her feel "beautiful."
Now: Applegate, 45, who once told Cosmopolitan, "I never looked in the mirror and thought I was a pretty girl," married LeNoble (with whom she has daughter, Sadie, 5) in February 2013. Also in 2013, she returned to the big screen in Anchorman 2: The Legend Continues. "I kind of thought, 'It’s 10 years later, if I’ve got 10 more pounds on me than [in] the first one then I think it’s completely acceptable,' ” she told Fitness.
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Most Beautiful 2011: Then a judge on American Idol and married to Marc Anthony, Lopez said she was "at my happiest" when home with her husband and their toddler twins. "Just being able to touch my face and rub my eyes and put my fingers in my hair and not having to worry about messing it up. It’s so much better.” She also reminded readers that looking good is "part of my job," saying the workouts, portion control and beauty regimen could be tough. “I don’t want anybody thinking it’s easy. It does take time and it’s hard work. HDTV wide-screen is nobody’s friend!”
Now: Lopez's "toddlers" are full-blown kids at age 9, she has the hit NBC series Shades of Blue, a Vegas residency, an upcoming reality competition series World of Dance and she's happily dating former New York Yankee Alex Rodriguez. She's since split from Anthony, though the two are "like best friends," the 47-year-old said. "We share something very special in the kids, and we know that. I'm always gonna be there for him, he's always gonna be there for me."
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Most Beautiful 2012: It was only a matter of time before Beyoncé earned the title of World's Most Beautiful. But it was after she welcomed daughter Blue Ivy that the songstress slash actress slash mogul actually felt worthy of the title. "I feel more beautiful than I've ever felt because I've given birth," she told PEOPLE. "I have never felt so connected, never felt like I had such a purpose on this earth."
Now: Thirty-five years old, Beyoncé continues to wow her fans with her music and its message, so it's safe to say that Queen Bey is as beautiful as ever. The singer is also currently expecting twins with husband Jay Z.
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Most Beautiful 2013: That year, Paltrow was promoting her new cookbook, It's All Good, her new film, Iron Man 3, and her partnership with trainer Tracy Anderson. The mom-of-two (and wife of Coldplay's Chris Martin) was also feeling happy and healthy. "I'm more in proportion now than I was when I was 20, so I feel better in a bathing suit now than I did before I had kids," she said. "But I think one of the most beautiful things about growing up is this self-acceptance that starts to happen." Her tips for staying beautiful included taking a nightly bath and washing her face with a hot washcloth.
Now: The 44-year-old has majorly grown her footprint in the lifestyle space thanks to her website and newsletter goop, which expanded into a skincare line and soon, a clothing collection. Though she consciously uncoupled from Martin, the two remain some of Hollywood's friendliest exes and co-parents, and in 2014, she moved on with producer Brad Falchuk. She also continues to induce #FOMO with her Instagram account, which chronicles her travels — and delicious meals.
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Most Beautiful 2014: She stunned on red carpet after red carpet during awards season, eventually nabbing the Oscar for Best Supporting Actress for 12 Years a Slave. Being named World's Most Beautiful, Nyong'o hoped she would help to challenge antiquated perceptions of beauty. "It was exciting and just a major, major compliment," she said of the title. "I was happy for all the girls who would see me on [the cover] and feel a little more seen."
Now: Her career hasn't stopped since: The 34-year-old was a part of what is now the best-selling film of all time, Star Wars: Episode VII - The Force Awakens (and will return in Episode VIII), and lent her voice to the live action adaption of The Jungle Book, as well as making her Broadway debut in the play Eclipsed.
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Most Beautiful 2015: When she was named PEOPLE's Most Beautiful Woman in 2015, the actress simply laughed. "No, really. I just said, 'That's ridiculous,'" she told PEOPLE. What really makes Bullock feel beautiful is her role as mother to her son, Louis. "What is beautiful is the honor of being Louis' mother," she said.
Now: Sandra has her hands full at home – she welcomed a sibling for son Louis last year, daughter Laila, who she adopted. “When I look at Laila, there’s no doubt in my mind that she was supposed to be here,” the 52-year-old told PEOPLE of her daughter.
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Most Beautiful 2004 & 2016: Aniston, who'd just wrapped up her wildly successful sitcom Friends when she landed on the cover of PEOPLE as the WMB for the first time, confessed to plastering on makeup in her younger, more insecure days. When she finally stopped, "I'd have people say, 'God, you look so much better.'"
When she was honored with the title for the second time last year, Aniston defined beauty as: "Inner confidence. Peace. Kindness. Honesty. A life well-lived. Taking on challenges and not feeling shame for things that haven't gone the way you felt they should have. And not feeling like a failure or allowing people to critique your life and make you feel like you've failed at something. That's just toxic noise."
Now: In January, Aniston revealed to Variety that she's considered returning to the small screen. "I've thought about it a lot," the 48-year-old said. "That's where the work is. That's where the quality is. At this point in my career, I want to be part of wonderful stories, exciting characters, and also just having a good time … When you're in your 20s, going away from home was an adventure — meeting new people, seeing other parts of the country or world was so exciting. Now it's really about wanting to stay closer to home and just enjoying your time."
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