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19 Photos Of Britney Spears Through The Years That'll Fill You With Nostalgia

Often referred to as the “Princess of Pop,” Britney Spears is credited with influencing the revival of teen pop during the late 1990s and early 2000s. As if anyone could forget, the superstar’s first two studio albums, ...Baby One More Time (1999) and Oops!... I Did It Again (2000), became two of the best-selling albums of all time. Not to mention “... Baby One More Time” was named the “greatest debut single of all time” by Rolling Stone in 2020. Did anyone not have her poster hung up on their bedroom wall? An undeniable pop icon, the blonde bombshell born in Mississippi has sold over 100 million records worldwide and, according to Forbes, was the highest-paid female musician of 2002 and 2012. And, since the inception of the internet in 1983, the singer has topped the list of most searched celebrities seven times in twelve years, making her one of the most searched people on the planet.

Regardless of the ups and downs the singer has faced, she will always be the ultimate #queen. Here are 20 photos of Britney Spears through the years that are guaranteed to make you nostalgic.

1993 — Meet the Mickey Mouse Club Star

In 1993, at only 11-years-old, Spears acted and sang in Season 6 of the US variety show, The All-New Mickey Mouse Club. "It was a really good time," Spears told Entertainment Tonight about her experience on the show in 2018. "It was probably one of the most special times in my life." Along with fellow future stars Justin Timberlake, Christina Aguilera, and Ryan Gosling, Spears apparently impressed casting directors at the auditions, which landed her the iconic role.

1997 — A Star is Born

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At only 15-years-old, Spears signed with Jive Records in 1997, which launched a music career for the history books.

1998 — Oh, baby, baby

In January 1999, Spears released her debut album ...Baby One More Time, which debuted at No. 1 on the Billboard charts. Since she was only 16-years-old at the time, critics were outraged by the “sexy” schoolgirl outfit she rocked in her 1998 music video for “...Baby One More Time,” but Spears argued that other girls her age were dressing in far sexier outfits. "There are so many other teenagers out there that dress more provocatively than I do and no one says anything about them," she told Entertainment Weekly in 2001.

2000 — The Classic All-White Outfit

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At 2000 Grammy Awards, Spears was nominated for Best Female Pop Vocal Performance, Best New Artist, and Album Of The Year. At the Billboard Music Awards the same year, she won Best Female Artists, and that was only the beginning of the countless awards the pop princess would take home in the future.

2001 — The Iconic Denim Duo

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If there’s one iconic Britney photo fans can never forget, it’s this decked-out-in-denim snapshot of Spears and her then-boyfriend Justin Timberlake at the 2001 American Music Awards. The power couple dated from 1998 to 2002, at which point they split. When Timberlake released his “Cry Me a River” music video in November that year, it featured a Spears lookalike who cheats on him, which sparked speculation infidelity on her part caused their split. (Timberlake apologized for how he treated Spears in a 2021 Instagram post, however, hinting where there’s smoke, there’s not always fire.)

2001 — A Snakey Moment in History

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Remember when Spears danced with a real, live, python? The singer performed “I'm A Slave 4 U” at the 2001 MTV Video Music Awards, making award show performance history.

2002 — Not A Girl, Not Yet A Woman

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Spears tried her luck at acting in 2002 when she starred in her first feature film, Crossroads, alongside Taryn Manning, Zoe Saldana, and Anson Mount.

2003 — The Legendary Lip-Lock

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The kiss. The passing of the torch. Whatever you want to call it — the lip-lock Spears and Madonna shared at the 2003 MTV VMAs was one of Spears’ most unforgettable moments. Aside from showing Madonna some extra love, Spears released her fourth album in 2003 titled In The Zone, which featured her hits “Toxic” and “Me Against the Music.”

2004 — Wedding Vibes?

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Spears married childhood BFF Jason Alexander at the Little White Wedding Chapel in Las Vegas in January 2004 after a long night out on the town. "It was just crazy, man," Alexander told Access Hollywood. "And we were just looking at each other and said, 'Let's do something wild, crazy. Let's go get married, just for the hell of it." Yet 55 hours later, the marriage was annulled. The white outfit Spears wore to the MTV VMAs looked a little like a wedding dress, don’t you think?

2004 — Actual Wedding Vibes

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Spears married backup dancer Kevin Federline on October 6, 2004, after meeting him at an LA nightclub only two months earlier (and eight months after her first marriage was annulled). "I met her at a club in Hollywood, Joseph's. Our eyes met and that was it. We just hit it off right away," Federline told People in 2008. "I was madly in love with her. Everything just seemed so right. I didn't see it as too fast or too slow."

2005 — There’s A Bun In The Oven

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In 2005, Spears confirmed rumors that she was pregnant with her first child. She and Federline welcomed their baby boy, Sean Preston Federline, on Sept. 15, 2005.

2006 — And Anotha One

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Only a year after her first son was born, Spears and Federline welcomed their second baby boy, Jayden James Federline, on Sept. 12, 2006.

2008 — Get It, Girl: Award Season

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Spears released her sixth album Circus, featuring her hits “Piece of Me” and “Womanizer” in 2008. That September, she took home the prize for Video of the Year, Best Female Video, and Best Pop Video for “Piece of Me” at the MTV VMAS.

2011 — Another Day, Another Album

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On March 25, 2011, Spears released her seventh studio album, Femme Fatale, with Jive Records.

2012 — Don’t Judge Her

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Spears became a judge on Season 2 of the hit show X Factor US, appearing alongside British music mogul, Simon Cowell, record executive L.A. Reid, and Demi Lovato.

2016 — All About The $$$

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Spears landed a Vegas residency called Britney Spears: Piece of Me, and by the conclusion of her shows in 2018, she’d earned about $140M according to Billboard mag. Get it, girl!

2018 — New Year, New Beau

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The superstar made her relationship with model Sam Asghari public for the first time in 2018 when she took him with her to the GLAAD Media Awards in Beverly Hills. Not only did she have a gorgeous hunk on her arm, but the singer also took home the coveted Vanguard Award at the show.

2020 — Time For Some Quality Time

These days, Spears loves spending days with her sons. "My two lil men's birthdays are this week!!!!!! You guys are getting older and so big and are waaay cooler than me !!!!! I love you both to the moon and back," she wrote in a Sept. 12, 2020, Instagram post.

2021 — Keeping Fans In The Loop

Today, Spears continues to make headlines just being her unique and beautiful self. With numerous Instagram posts and stories detailing her everyday life, along with videos of her classic dance moves, Spears is keeping fans in the loop, and they still can’t get enough. Gimme, gimme more!