Britney Spears: The Evolution Of A 90’s Icon In Pictures

1 Britney and Christina

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This picture is from 1994.

The two singers were good friends, both being part of the Mickey Mouse Club.

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2 Basketball Player

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This picture is from 1997.

Britney was part of the basketball team at her school, Parklane Academy.

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3 Teenage Shooting

Britney Spears: The Evolution Of A 90’s Icon In Pictures
William Rutten
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This picture is from 1999.

Britney had then participated in a shooting with the photographer William Rutten.

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4 “Sometimes” Music Video

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It was on April 9 and 10, 1999 that Britney filmed the video for her song “Sometimes”.

The video was shot at Paradise Cove in Malibu and was released on May 6, 1999 on Total Request Live.

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5 School Dance

Britney Spears: The Evolution Of A 90’s Icon In Pictures
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This photo is from January 11, 1999.

Britney was then participating in the American Music Awards.

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6 Promotional Photoshoot

Britney Spears: The Evolution Of A 90’s Icon In Pictures
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This picture of Britney was taken in 1999.

The singer was participating in a promotional photoshoot in Munich.

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7 #FreeBritney

Britney Spears: The Evolution Of A 90’s Icon In Pictures
The Daily Beast
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This picture was taken in June 2000.

It was the singer’s personal assistant, Felicia Culotta, who captured the shot on the set of the music video “Lucky”.

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8 Hanging Out

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In this photo, we can see Britney surrounded by her lover of the time Justin Timberlake, but also Fergie and Lance Bass, as well as some friends.

Stars also take the time to spend good moments with their friends between their various obligations!

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9 First Serious Relationship

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This photo was taken in 2000 while Britney was attending the MTV Music Video Awards at Radio City Music with her then lover, Justin Timberlake.

Britney and Justin were a couple from 1999 to 2002.

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10 Floral Cowboy

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This picture of Britney was taken in 2000.

She appeared on The Today Show, and pleased her fans with a little performance.

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11 Crazy 2K Tour

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This picture was taken in 2000.

Britney was then in the middle of her Crazy 2K Tour in Waikiki.

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12 Denim Shirt

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Everyone knows Britney’s love for denim clothing!

Doesn’t she look great in this picture? Absolutely simple and beautiful!

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13 Control Freak

Britney Spears: The Evolution Of A 90’s Icon In Pictures
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This picture was taken on September 7, 2000.

Britney had just finished a show and then changed into this TIGI Bed Head Control Freak crop-top.

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14 Happy Girl

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This image is from the documentary “Framing Britney Spears”, February 5, 2021 episode of The New York Times Presents.

We can see a young Britney happy and smiling!

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15 Wild Performance

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During the VMAs of 2001, Britney had made a performance out of the ordinary which marked the spirits.

Not only was her look repeated several times, but the fact that she performed “I’m a Slave 4 U” with an albino Burmese python in her arms surprised many!

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16 Young Woman

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This type of shirt was very popular in the early 2000s.

As a fashionable young adult pop star, Britney had obviously proudly worn her “Jesus is my homeboy” t-shirt!

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17 Behind The Scene

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This picture is a behind the scene from the video shoot of the song “Oops! I Did It Again”.

The video was shot in 2001, when the singer was 19 years old.

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18 Crossroads

Britney Spears: The Evolution Of A 90’s Icon In Pictures
The Guardian
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Britney’s first film starring role was as Lucy Wagner in the movie Crossroads (2002).

The film was a box office success, and the singer’s acting talents were revealed.

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19 Controversial Kiss

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That moment when Britney and Madonna kissed at the 2003 VMAs made people talk a lot.

During this number, Madonna also kissed Christina Aguilera, but this kiss, unlike the one with Britney, went rather unnoticed.

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20 Family

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The Telegraph
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In this photo, we can see Britney with her parents, Jamie and Lynne, and her brother Bryan.

They were all gathered in a Hardwood Suite at the Palms Casino Resort in Las Vegas the launch party for the new Palms Home Poker Host software co-created by Jamie.

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21 Britney and Paris

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Britney and Paris Hilton have been friends for many, many years.

They even spent time together in Malibu during the summer of 2020.

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22 Tribute

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This photo was taken in 2017 at the Radio Disney Music Awards, when several singers performed a medley of Britney’s greatest hits.

In this photo, alongside the singer, are, from left to right: Kelsea Ballerini, Sofia Carson, Hailee Steinfeld, and Jamie Lynn Spears.

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23 We Are All Dreamers

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The Blast
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Britney shared this photo on her Instagram account on December 22, 2017.

In the caption, she wrote, “We are all Dreamers. Tell Congress to pass the #DreamAct”.

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24 Proud Mother

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This photo was taken in London in August 2018.

It shows Britney proudly posing with her two sons, Jayden and Sean.

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25 Red Carpet

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This photo was taken on July 22, 2019 in Los Angeles.

Britney walked the red carpet there for the premiere of Once Upon a Time in Hollywood.

Anita Parker

Anita is the joy of life incarnate. Always ready to go out and take on challenges, she likes to talk about everything through her articles, whether it's her favorite beauty products or her outings to restaurants.

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