PEOPLE's Most Beautiful: A Look Back at the Covers

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.”

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.”

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.

Crawford was a mere 27 when the Revlon supermodel (and then-wife of Richard Gere) appeared on the cover. Her fellow cover models were Whitney Houston, Andrew Shue (of Melrose Place) and Catherine Deneuve.

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.

No Arquette, no Dirt: She was only 30 (and four years into a romance with Michael Keaton) when her role as Monica Gellar on Friends landed the actress the cover (with Halle Berry and George Clooney).

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.

Cruise was 34 — and still married to Nicole Kidman — when he graced PEOPLE’s 50 Most Beautiful cover with Toni Braxton (her second appearance) and Drew Barrymore.

He was the king of the world at 23, starring in the mega-hit Titanic and on the cover of the Most Beautiful issue. Sharing the cover were Gwyneth Paltrow and Julia Louis-Dreyfus.

The actress was 41 when she graced PEOPLE’s cover a second time. Sandra Bullock and Ben Affleck also shared it.

Fresh from three hit films — Notting Hill, Runaway Bride and Erin Brockovich — Roberts was only 32 when she appeared on the 2000 cover, alongside George Clooney and Faith Hill.

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.

One year after her divorce from Cruise, Kidman, then 34, had just won a Golden Globe Award (and scored an Oscar nod) for Moulin Rouge. Her fellow cover stars were Josh Hartnett and Jennifer Aniston.

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!).

The actress talked with PEOPLE about the end of Friends — and her life with then-husband Brad Pitt. Sharing the cover with Aniston, then 35, were Beyoncé, Johnny Depp and Pitt.

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!”

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.

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.

Hudson’s 4-year-old son Ryder dominated the conversation when the actress was named Most Beautiful at age 29. Sharing cover space with her: Halle Berry and Patrick Dempsey.

With her cancer battle behind her, Applegate then 37, was radiant on her PEOPLE cover, shared with Jennifer Lopez, Robert Pattinson and Cindy Crawford, among others.

Lopez’s cover reveal was extra-special: it happened during American Idol, which she was judging at the time. The mom of two, then 41, was joined by Mila Kunis and Ashton Kutcher on her issue.

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.

Though Paltrow’s cover was polarizing to readers, her message on natural beauty (and staying fit) was a simple one. The mother of two, then 40 — and joined on the cover by fresh faces Jennifer Lawrence and Kerry Washington — also touched on the topics of motherhood and cooking with her late father.

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.

“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.”

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 husband Justin Theroux. “He makes me laugh. He’s so interesting and so interested … and he’s just a good man.”

Covering the issue for a record fifth time (her 2010 cover was shared with Sandra Bullock’s baby news), Roberts told PEOPLE she’s “flattered” by the title and believes the best is yet to come: “I think I’m currently peaking.”