Michelle Pfeiffer, 1990
Eleven PEOPLE editors decided to put out a list of the 50 Most Beautiful People in the World, taking submissions from readers, fellow staffers and casting directors and modeling agents. Pfeiffer, then 32, received the top honor, though PEOPLE editors wrote they learned three things from the process: “That there is no such thing as perfect beauty. That people have blessedly different ideas about what’s beautiful. And that most people are beautiful in some way, and that’s about as beautiful as anybody really needs to be.”
Julia Roberts, 1991
Editors called the 23-year-old “a Botticelli beauty,” and model maven Eileen Ford seconded that superlative. ”She is one of the few new great beauties,” she said. “She doesn’t look like she’s been dragged through the mud like a lot of them now do.”
Jodie Foster, 1992
The actress, then 29, was fresh from her second Oscar win (for Silence of the Lambs) when she appeared on PEOPLE’s Most Beautiful issue. Sharing the honor were Mel Gibson, Elizabeth Taylor and Denzel Washington.
Cindy Crawford, 1993
Revlon model Crawford was a mere 27 — and married to Richard Gere — when she appeared on the cover. Her fellow cover models were Whitney Houston, Andrew Shue and Catherine Deneuve.
Meg Ryan, 1994
The actress, then 32, was still married to Dennis Quaid and promoting the film When a Man Loves a Woman when she made the cover of PEOPLE’s 50 Most Beautiful issue. Daniel Day-Lewis, Toni Braxton and — whoa! — Joey Lawrence (then on Blossom) also appeared on the cover.
Courteney Cox, 1995
Mel Gibson, 1996
The actor, then 40, had just earned his Oscar wins for Best Director and Best Picture (for Braveheart) when he appeared on the cover (alongside Michelle Pfeiffer, Brad Pitt and Brandy) for a second time.
Tom Cruise, 1997
Leonardo DiCaprio, 1998
Michelle Pfeiffer, 1999
Julia Roberts, 2000
Catherine Zeta-Jones, 2001
The new mom (to son Dylan, then 9 months old) was 31 and the star of Traffic when she landed the cover of PEOPLE’s 50 Most Beautiful issue, alongside Katie Couric and Benicio Del Toro.
Nicole Kidman, 2002
Halle Berry, 2003
The actress, then 36, had just made history as the first-ever African-American actress to win an Academy Award for Best Actress (for Monster’s Ball,) and was about to reprise her role as Storm in X2: X-Men United when she graced the cover. Also on the cover were Britney Spears and George Clooney (his third appearance!).
Jennifer Aniston, 2004
Julia Roberts, 2005
The 37-year-old star’s twins Hazel and Phinnaeus were just 5 months old when Roberts landed her next WMB cover, which declared her a “Hot Mama!”
Angelina Jolie, 2006
Jolie was 30 when she pulled double duty for the cover, which doubled in size from 50 to 100 Most Beautiful. Then pregnant with daughter Shiloh, the actress was named among the world’s Most Beautiful, and she, with then-partner Brad Pitt and children Zahara and Maddox, were called the World’s Most Beautiful Family.
Drew Barrymore, 2007
The newly single star — Barrymore had just split from longtime boyfriend Fabrizio Moretti — appeared on PEOPLE’s Most Beautiful cover for the first time at age 32. In an unprecedented move, she posed without makeup for a photo shoot featured inside the issue. Also posing sans makeup: Jessica Biel, Rihanna and Jessica Alba.
Kate Hudson, 2008
Christina Applegate, 2009
Jennifer Lopez, 2011
The singer arrived to her cover shoot in a helicopter — and obviously the glam didn’t stop there. The new mom, 30, didn’t share her cover space with any other beauties — but her issue did include an ode to the “beauty of the photobomb,” likely a WMB first.
Gwyneth Paltrow, 2013
Lupita Nyong'o, 2014
The inspiring Oscar winner – joined on the cover by Julia Roberts (again!), Jennifer Lawrence and Julianna Margulies – was a fun pick in part because of her amazing fashion sense. The then-31-year-old played dress-up in a bunch of gowns in a seriously glam video, and was filmed meeting her beauty icon, model Alek Wek.
Sandra Bullock, 2015
“That’s ridiculous,” was the 50-year-old’s reaction to earning the title that year. “What is beautiful is the honor of being Louis’ mother,” she added of parenting her 5-year-old son. “Be a good person, be a good mom, do a good job with the lunch, let someone cut in front of you who looks like they’re in a bigger hurry. The people I find most beautiful are the ones who aren’t trying.”
Jennifer Aniston, 2016
Earning the title for a second time gave the 47-year-old actress “this sort of very excited, teenage-y kind of moment,” she told PEOPLE. Her interview touched on aging — “It’s funny, it’s a really quick transition from not a care and now all of a sudden, we’ve got to really be mindful of what we put inside our bodies,” she said — and life at home with then-husband Justin Theroux. “He makes me laugh. He’s so interesting and so interested … and he’s just a good man.”
Julia Roberts, 2017
Covering the issue for a record fifth time (her 2010 cover was shared with Sandra Bullock’s baby news), Roberts told PEOPLE she was “flattered” by the title and believed the best is yet to come: “I think I’m currently peaking.”
In 2018, PEOPLE shifted the title from “Most Beautiful” to the “Beautiful Issue” — and Pink, 38, was the perfect person to usher in the new era. The mom of two talked about raising her children to be strong and how life with husband Carey Hart involves laughing a lot.
“[We] try not to take life too terribly seriously,” she said. “It’s all about our family unit and time spent together, and much less about external stuff.”
Jennifer Garner, 2019
Growing up in West Virginia, 2019 cover star Garner insisted her own style could initially be described as “band geek-chic,” she joked to PEOPLE. “I was so not one of the pretty girls that I just bypassed insecurity and didn’t see myself as attractive at all. It was not part of my life.”
Yet the actress was grateful to her family for keeping her so grounded. “I felt good about myself back then! That is the lucky trick,” she added. “Looks weren’t a big deal in my family. I don’t think my parents ever said ‘You’re pretty’ and so we just didn’t think about it.”