Britney Spears turns 44! See the original pop princess' life in 5 iconic photos


The 'Oops!…I Did It Again' singer, who is known as the 'Princess of Pop', turns 44 as she lives outside of the public eye.


britney spears black lace dress smiling billboard awards 2016© Lester Cohen/BBMA2016
Tess HillNews and Features Writer
December 2, 2025
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Britney Spears is celebrating today! The iconic pop princess, and iconic Sagittarius, turns 44. Britney broke into the entertainment industry when she was just 11 years old and debuted with her best selling album, …Baby One More Time in 1999.

The singer's four decade life has had its fair share of hardships. After public scrutiny and struggles with her mental health, Britney was placed under a conservatorship from 2008 until 2021 after she publicly testified against her family.

These days, Britney has withdrawn from the typical celebrity life, residing in California and sporadically posting to her 42 million Instagram followers. To celebrate her 44th birthday, HELLO! looks back at the five most iconic photos of Britney's life.

© Getty

Britney perfected the early 2000s look

Her first album was released in 1999, but Britney was on every early 2000s girl's mood board. She strutted on stage with her mic attached to her head, and made history. During her 2000 Oops!... I Did It Again tour, she wore a silver set that showed off her mid-drift.

© KMazur

Her very first Grammys

The pop princess performed for the first time at the Grammys in 2000, where she put on a memory display of "…Baby One More Time" and "From the Bottom of My Broken Heart." To the ceremony, Britney wore a white Randolph Duke gown, which she accessorized with a white fur stole from Oscar de la Renta and a diamond necklace.

© Getty

The denim on denim look no one will forget

In 2001, while she was in a relationship with Justin Timberlake, Britney wore an outfit for the history books. She and Justin showed up to the American Music Awards in Canadian tuxedos. Britney wore a denim gown, with a silver belt embellishing her waist, while Justin wore a denim suit paired with a denim hat.

The couple dated for three years, from 1999 to 2002, after first meeting on the set of The All-New Mickey Mouse Club in 1992.

© Getty

Britney and the snake

Also in 2001, the singer performed at the VMAs with an albino Burmese python named Banana to her hit song, "I'm a Slave 4 U." In her memoir, The Woman in Me, Britney explained: "The plan was for me to sing 'I'm a Slave 4 U,' and we decided I would use a snake as a prop. It's become an iconic moment in VMAs history, but it was even more terrifying than it appeared."

She continued: "All I knew was to look down, because I felt if I looked up and caught its eye, it would kill me."

© Alamy Stock Photo

The Woman in her

Britney's life is one that should be written about. And on October 24, 2023, two years after her conservatorship ended, the singer released her memoir, The Woman in Me. Britney details her intense childhood, her many relationships with the men of Hollywood, and her public mental health breakdowns. Within a week of its release, the memoir became a #1 New York Times best-seller. As of 2024, a film adaptation directed by Jon Chu of Wicked is currently in the works. 

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