Flashback: Britney Spears on 'Rolling Stone' and More Iconic Celebrity Magazine Covers!

From Britney on 'Rolling Stone' to Demi on 'Vanity Fair,' take a look at back at the most memorable covers!

From Britney Spears' risque cover for Rolling Stone to Demi Moore showing off her pregnant belly on Vanity Fair, over the years, some of our favorite celebrities have graced magazine covers in photos that we could never forget. Do you remember them all?

Brooke Shields - Time (1981)

Brooke Shields Time Magazine Cover

Courtesy of Time

Fresh off her success from The Blue Lagoon in February of '81, the teen actress posed for the cover of Time, which was quite a feat for someone at such a young age. With her big hair and trademark eyebrows, it is no surprise that the magazine chose her to document their '80s look cover story! Now over 30 years later, Shields is still sporting a striking look as a model and actress -- but with two kids of her own!

Jodie Foster- Interview (1987)

Jodie Foster Interview Magazine Cover

Courtesy of Interview

A very youthful Jodie graced the cover of Interview in August of '87 at a time of great growth in her career -- she would star in Stealing Home and take her Oscar-winning turn in The Accused just a few months later. Flash-forward to today, and Foster is one of the most respected actresses -- and directors -- in Hollywood, and had the entire audience at this year's Golden Globes in tears when she started to finally open up about her sexuality.

Madonna - Vanity Fair (1986)

Madonna Vanity Fair Magazine Cover

Courtesy of Vanity Fair

The Material Girl had already been blowing up the entertainment world with big hits such as "Like a Virgin" and "Borderline," as well as a starring turn in Desperately Seeking Susan. But with the release of Who's That Girl in 1986, she went for a completely different look -- her short, bleach-blonde bob marked the beginning of Madonna's ever-evolving appearances, something Vanity Fair dubbed on the December cover as "Change of Face." And that is one thing that Madonna has continued to do ever since -- change.

Julia Roberts - GQ (1991)

Julia Roberts GQ Magazine Cover

Courtesy of GQ

With the successful release of Pretty Woman oppposite Richard Gere and Flatliners with Kiefer Sutherland in 1990, the decade got off to a great start for Roberts -- so it was no surprise when she rocked the cover of GQ in February of '91 to promote her latest project, Sleeping With the Enemy. The thriller was just the next jumping-off point for the actress, who kept on snagging killer roles. With multiple awards and plenty of blockbuster hits since, she is still one of the biggest film stars in the world.

Demi Moore - Vanity Fair (1991)

Demi Moore Vanity Fair Magazine Cover

Courtesy of Vanity Fair

This famous cover of Vanity Fair was shot more than 20 years ago in August of '91, and it is still referred to every time another pregnant celebrity poses nude for a magazine cover. Moore showed off her au natural look for this historic cover back when she was pregnant with her and Bruce Willis' second daughter, Scout. The family may have been through many ups and downs since then, but we do wonder how her now-21-year-old daughter must feel now, looking back at this cover.

Janet Jackson - Rolling Stone (1993)

Janet Jackson Rolling Stone Magazine Cover

Courtesy of Rolling Stone

The youngest of the Jackson family shot this iconic cover back in August of '93, but it is still talked about today for its racy depiction of a mystery man groping the pop star. It was later revealed that those were, in fact, the hands of Jackson's husband at the time: Rene Elizondo. Now that Jackson has a new hubby, could we soon see another iconic cover like this one?

Jennifer Aniston - FHM (1996)

Jennifer Aniston FHM Magazine Cover

Courtesy of FHM

No one will ever forget the hair trend known as "The Rachel," the 'do that Aniston sported in the early days of Friends and girls around the country were clamoring to get for themselves. The actress rocked her hot style on the cover of FHM showing that she wasn't just about her hair -- that she could be sexy, too! And she was off to a good start -- she ended up becoming the biggest star to come off of the hit sitcom when it ended 8 years later!

Heidi Klum - Sports Illustrated (1998)

Sports Illustrated Magazine Cover

Courtesy of Sports Illustrated

With Klum in the news so much lately (from her split with Seal to her new gig as a judge on America's Got Talent), you would think that she has been in our world forever. But, in fact, after being born and raised in Germany, she really became part of the American celebrity landscape back in February of '98 with her sizzling photo shoot for cover of Sports Illustrated. Looking back at this shoot, would we have ever guessed the huge star power she would soon create?

Britney Spears - Rolling Stone (1999)

Britney Spears Rolling Stone Magazine Cover

Courtesy of Rolling Stone

Since the singer made her pop music debut in 1999 with "Baby... One More Time," the world has witnessed her (many) ups and downs in her life -- from her 55-hour marriage to Jason Alexander in 2004 to her messy custody battle over kids Sean and Jayden with ex Kevin Federline. (And let's not forget the night she shaved her head.) Spears was always trying to prove that she was "not that innocent," and she got her point across on the cover of Rolling Stone when she posed -- in a very provocative way for a then-17-year-old -- for the magazine for the first time in April '99.

Angelina Jolie - Rolling Stone (1999)

Angelina Jolie Rolling Stone Magazine Cover

Courtesy of Rolling Stone

It's weird to think back to the days of Jolie before her family-filled world of Brad Pitt and their six children. But when you flash back to August, '99, her career was just beginning to take off when she posed for the cover of Rolling Stone as part of their Hot List, pegging her as the "Devil Doll." The bad-girl image was the one that Jolie loved and continued to crave, through her marriage to Billy Bob Thornton. Now with Jolie's work with The UN and all of her children, will we ever see her doing this kind of iconic cover again?

Connect with Us
Follow Our Pins

Yummy recipes, DIY projects, home decor, fashion and more curated by iVillage staffers.

Follow Our Tweets

The very dirty truth about fashion internships... DUN DUN @srslytheshow http://t.co/wfewf

On Instagram

Behind-the-scenes pics from iVillage.

Best of the Web