See PEOPLE's 50th Anniversary Cover Stars Side by Side with Their First PEOPLE Cover

As PEOPLE celebrates its 50th anniversary with 11 celebrity cover stars, look back at their past cover stories through the years

PEOPLE is marking its 50th anniversary with some fan-favorite cover stars.

In honor of the milestone edition of the magazine, PEOPLE enlisted 11 celebrities (and one adorable corgi) in fields ranging from music, movies, TV, sports and more to appear on the cover.

Sexiest Man Alive alums Matthew McConaughey, Dwayne Johnson and John Legend reflect on their careers (and hunky titles), while Hollywood legends like Serena Williams and Oprah Winfrey open up about their trailblazing careers.

Though each of the celebrities has graced the cover of PEOPLE on countless occasions, we’re turning back the clock to look back at their first big, solo PEOPLE cover story.

Remember when a little Drew Barrymore graced the cover with Ricky Schroder and Henry Thomas? What about when Nicole Kidman appeared on the Most Beautiful People issue?

Take a trip down memory lane as you see PEOPLE’s 50th anniversary cover stars side by side with their first cover.

Reese Witherspoon’s PEOPLE Cover Story, Now and Then

One of Reese Witherspoon's first PEOPLE covers came in April 2002, when she was featured as one of "Hollywood's young brides." At the time, Witherspoon was married to actor Ryan Phillippe, with whom she later welcomed two children: their daughter Ava and their son Deacon.

Her first solo PEOPLE cover story came a year later as she was promoting Legally Blonde 2. "It was surreal," the actress told PEOPLE of her first cover story. "You can’t believe it’s happening. It’s like when your name is in a crossword puzzle. (It’s because I have a lot of vowels in my name!}"

Jennifer Aniston’s PEOPLE Cover Story, Now and Then

One of Jennifer Aniston’s first PEOPLE covers was notably alongside her Friends costars in April 1995 as the cast took the magazine behind the scenes of the hit sitcom.

For PEOPLE's 50th anniversary issue, Aniston reflected on the "magic" of the iconic show and the fun of shooting the cover together, noting it was such an "exciting" time in her life.

"It’s still exciting," she added, "but we’ve had more experiences. We’ve learned more lessons. There’s a little more behind us."

Viola Davis’s PEOPLE Cover Story, Now and Then

One of Viola Davis' first PEOPLE covers was in March 2017, in which she reflected on her incredible journey as an actress as well as her historic Oscar win for Best Supporting Actress in Fences. “‘I cannot believe my life,'” she said at the time. “I just can’t. I’m so blessed.”

Fast forward to her cover story for PEOPLE's 50th anniversary and Davis is still amazed by the trajectory her career has taken. Reflecting on her Oscar win, specifically, she said the moment was like "pulling a rabbit out of the hat."

"Viola, you dreamed the biggest dream in your life and you made it happen," she explained. "And my mom, who's in memory care now, what I remember with this dress - when I put it on, she cried. I remember her crying because I think she felt the same way that I felt. Little country girl from St. Matthews, South Carolina, that she birthed me and she birthed this."

Nicole Kidman’s PEOPLE Cover Story, Now and Then

In May 2002, Nicole Kidman graced the cover of PEOPLE's Most Beautiful People issue. In the cover story, Kidman opened up about feeling comfortable in her own skin amid a time of transformation, in both her personal life and career.

"I don't feel comfortable saying, 'Okay, now I'm going to be beautiful,'" she said in the issue. "That leaves me feeling shy and embarrassed. I can do it as a character, but I would never do it as Nicole. I'm not really into the full-on seduction stuff. I much prefer just being who I am."

In PEOPLE's 50th anniversary issue, Kidman opened up about her 25 years in Hollywood and all she's done both on and off screen.

"I've shared my ups and downs with the world and also shared all of my work," she noted. "That's been my life...my children, my husband [Keith Urban] and my work."

Michael J. Fox’s PEOPLE Cover Story, Now and Then

Michael J. Fox had one of his first PEOPLE cover stories in April 1987, two years after the incredible success of his film Back to the Future. Since then, he has appeared on countless covers of PEOPLE, noting that the magazine has been a "weird chronicler" of his life in a sense.

"I would imagine if I looked back at it, it would pick things out," he told PEOPLE for the 50th anniversary issue. "I remember that. I remember that. I remember that as well. I know not everybody has that library of their life at their disposal, but PEOPLE has provided one for me, and I appreciate it."

Oprah Winfrey’s PEOPLE Cover Story, Now and Then

One of Oprah Winfrey’s first PEOPLE cover stories was in 1987, a year after her hit talk show The Oprah Winfrey Show aired. In the issue, she opened up about her past as well as her journey as a trailblazer for women everywhere.

In PEOPLE's 50th issue, she reflected on her past with gratitude. When asked what advice she'd give to her younger self, Oprah replied: "Hold on, girl. Hold on to yourself."

"The most important thing is to remain centered so whether you're on the cover of PEOPLE or not, your identity isn't tied to what the rest of the world says it is," she continued. "Being able to not get confused by what the external says about your internal self is the most important thing for anybody who's going to take the fame ride."

Dwayne Johnson’s PEOPLE Cover Story, Now and Then

Dwayne Johnson notably appeared on the cover of PEOPLE in November 2016 when he was named PEOPLE's Sexiest Man Alive, a title he has been quite proud of in the years following.

"At the end of the day, you’ve got to give the people what they want!" Johnson told PEOPLE of his sexy achievement. "Guys usually try to downplay it, but don’t give me that s---. It’s cool! It’s awesome! And I’ve been saying it since birth: I am, in fact, the sexiest man alive. And very humble, so it goes hand-in-hand."

Drew Barrymore’s PEOPLE Cover Story, Now and Then

Drew Barrymore was just a little kid when she appeared on PEOPLE in November 1984. The cover story, which also featured Ricky Schroder and Henry Thomas, focused on child stars and their rise to fame in Hollywood.

For PEOPLE's 50th anniversary issue, Barrymore opened up about growing up in the spotlight at such a young age, noting the magazine has been "a safe place" for her amid the highs and lows in her life.

"[It's] a real marker of what the heck is happening in my life," she explained. "I've done covers of PEOPLE that have shown that I'm flawed and figuring it out, that I'm trying to get my life back on track, that I've become a mom, that I've gotten married, that I'm doing something right at work or starting a new endeavor in this talk show. At every interval that's been symbolic in my life, there is a PEOPLE Magazine cover to show for it.”

Matthew McConaughey’s PEOPLE Cover Story, Now and Then

Matthew McConaughey is yet another Sexiest Man Alive alum gracing the cover of PEOPLE's 50th anniversary issue. The actor was given the title in November 2005, a transformative time in his career as he began to pivot away from comedies and move into more dramatic roles like 2011's The Lincoln Lawyer and his Oscar-winning turn in 2013's The Dallas Buyer's Club.

As PEOPLE celebrates its 50th anniversary with him on the cover, his life has transformed even more since that 2005 issue as he's gotten his greatest gig of all: being a dad of three.

"I can't think of anything more important," McConaughey tells PEOPLE about raising his children alongside wife Camila Alves. "Having children, I know, has made me a better artist and a better actor. Kids see things for the first time all the time. Their questions are innocent. I've become a better storyteller because I have kids."

John Legend’s PEOPLE Cover Story, Now and Then

John Legend marks the third Sexiest Man Alive on PEOPLE's 50th anniversary cover. The singer was given the honor in November 2019, the same year he was the winning coach on The Voice and a year after he welcomed his second child with Chrissy Teigen.

When asked what advice he'd give his younger self, Legend noted that he wouldn't have much to say. "I look back and I'm like, 'It all worked out,'" he explained. "Even when things didn't work out in the moment, it's all led me to where I am. I don't really have a lot of advice for my younger self. I'm like, 'You’re going to mess up, and you’re going to figure it out.' Eventually I got to be on the cover of the Sexiest Man Alive issue, which I never would’ve dreamt of during this time."

Serena Williams’ PEOPLE Cover Story, Now and Then

PEOPLE's 50th anniversary issue actually marks Serena Williams' first PEOPLE cover, however, she has been a mainstay in the pages of the magazine since she was a teenager (including her 1999 spread above documenting her U.S. Open victory). She also covered Teen PEOPLE in 2000 for a special Olympics issue!

Speaking to PEOPLE about that 1999 U.S. Open win that turned her into a household name, Williams noted that her life changed completely as a result.

"That win really propelled me to the next level and it propelled me to being just…everywhere," she said. "It had been so long since an African American had won a Grand Slam — it had been a very, very long time. And I was the first to do it since Althea Gibson in the 50s. It pushed so many more amazing young Black women into the sport. And it was fun."

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