10 Memorable Young Britney Spears Moments

When thinking about the most danceable pop hits of the 2000s or the most quintessential and sought after Y2K outfits, one name comes to mind: Britney Spears.

The Mississippi native, 41, rose to fame at the turn of the century, and garnered millions of fans after sharing her vocal and choreography talents (as well as some unforgettable style moments), and as early aughts nostalgia dominated 2022, it’s hard to look back at that time without highlighting the “Princess of Pop” as a major inspiration.


From returning to music following her conservatorship freedom to tying the knot with husband Sam Asghari, Spears had a very memorable 2022. With that said, we rounded up ten of our favorite moments from the early days of the pop superstar’s career to help celebrate why she’s still a pop culture icon, in every sense of the word.


10 Memorable Young Britney Spears Moments

1. First Mickey Mouse Club Appearance — 1993

The show that started it all! In 1992, Spears got her first major gig while starring on the Mickey Mouse Club and giving viewers a glimpse of her many talents and charisma. She joined fellow cast members, including future boyfriend Justin Timberlake, Christina Aguilera, Keri Russell, Ryan Gosling and more.

After the show was cancelled in 1994, she went back to Mississippi to graduate high school, and then eventually impress her future record label with her vocal talents, leading to the release of her debut record, …Baby One More Time in January 1999.


2. “…Baby One More Time” Video Release — 1999

From its catchy lyrics to its infectious melodies, Spears’ lead single off her first album was a major hit, and often cited as one of the most influential pop songs and records of all time.

The accompanying video, which featured Spears dressed in a series of ab-baring, figure-flaunting outfits (such as a revamped schoolgirl uniform, a bright pink crop top and white pants, a sporty yellow tank and low-waisted red track bottoms, etc) also gave young viewers plenty of turn-of-the-century style inspo! The video also helped highlight Spears’ dancing skills and ultimately, now proves that she was always destined for superstardom.


3. Controversial Rolling Stone Cover — 1999

Spears has stunned on countless magazine covers over the years, but one of her most unforgettable cover shots is the one used for the April 1999 issue of Rolling Stone. Ever since its debut, the pic of then-18-year-old Spears lying on a bed with pink sheets while wearing a black bra top, polka-dot white short-shorts, and holding a Teletubbies stuffed toy and corded phone has sparked controversy.

To make matters even creepier, the cover story was titled, ‘Inside The Heart, Mind & Bedroom of a Teen Dream,’ which many fans still find inappropriate to this day, considering her age at the time and the rumor that she was pressured into posing for the shot, and never consented to it. Spears reportedly told the shoot photographer David LaChapelle that she “didn’t feel comfortable” with the sultry photo. Since the cover was released, it is instantly one of Spears’ most memorable, for many reasons.

As seen in Framing Britney Spears, the 2021 New York Times documentary (about her conservatorship battle and years-long struggles to cope with overwhelming fame since childhood), the over-sexualized image of Spears promoted by press at the time led to her 2007 breakdown and tumultuous personal life.

4. First Grammy Awards Appearance — 2000

While we now know Spears to be a Grammy winner and recipient of 8 nominations, there was a time when she was once a newcomer and graced the award show in a curve-hugging, glamorous white Randolph Duke gown.

While walking down the red carpet in February of 2000, Spears stunned fans in the Old Hollywood-esque frock that featured cut-outs along its halter neckline and a waist-emphasizing fit. With this dress, she paired a fur piece from Oscar de la Renta, silver heels and a sparkling diamond necklace.

Wowing viewers even more, Spears also performed at the ceremony, delivering an impassioned medley of her songs “From the Bottom of My Broken Heart” and “…Baby One More Time” while also completing an impressive choreographed routine. (We’ve been in awe of her ever since!) While Spears didn’t take home a trophy that night, she was notably honored with nominations for Best New Female Artist and Best Female Pop Vocal Performance for “…Baby One More Time.”


5. Iconic Matching Denim Outfit With Justin Timberlake — American Music Awards 2001

Spears confirmed her relationship with fellow singer and former Mouseketeer Justin Timberlake in 1999 after the two went public. In 2001, she opened up about their romance in an interview with The Observer. 

She said at the time, “With him, it’s still the same as I felt two years ago. But it is a deeper love now than when I was younger.” She went on, adding, “Like, we’ve gone through so much together and we’ve known each other since we were 12 years old. We know each other inside and out.” As the two dated while their careers skyrocketed, they also gave us plenty of pointers when it comes to Y2K couple fashion.

Perhaps their most memorable, coordinated outfits moment has to be their matching all-denim ensembles worn to the American Music Awards in 2001. As the dynamic duo graced the red carpet, they both wore entirely denim pieces (even down to some of the accessories!), with Spears rocking a strapless denim gown and sparkling silver belt and Timberlake donning a classic Canadian tuxedo look.

6. Super Bowl XXXV Halftime Show With Aerosmith — 2001

During the 2001 Super Bowl face-off between the Baltimore Ravens and the New York Giants, Spears made an epic appearance during the “Kings of Rock and Pop” halftime show, which was headlined by Aerosmith and *NSYNC. Spears, Nelly and Mary J. Blige all joined the talented group as special guests for a medley.

Fans will recall how Spears lent her vocal talents to a rendition of “Walk This Way” while singing with Steven Tyler and wearing a low-cut black crop top and low-waisted white pants with black stripes on the sides. For the performance, Spears once again showed off her vocal talents and dancing skills, all in early aughts fashion.

7. MTV VMAs Performance With Snake — 2001

Who could ever forget Spears’ 2001 MTV VMA “I’m a Slave 4 U” performance when she brought out a real, living snake to accompany her choreography routine? Spears sang, danced and emphasized her washboard abs in a lime green halter top with the massive serpent wrapped around her body, standing out as one of the most memorable VMA performances ever.

This only amplified Spears’ dedication to her craft and talents. After all, who else could perform such an extensive routine, hit impressive vocal notes and carry an amelanistic Burmese python all at once?



8. Crossroads Movie Release — 2002

Spears made her film debut in the teen drama flick Crossroads alongside a star-studded cast, including Zoe Saldana, Kim Cattrall, Taryn Manning and more. Spears portrayed Lucy Wagner, who ventures on a road trip with her friends following their high school graduation.

Although the film received mostly negative reviews from critics at the time, Spears’ performance was praised by many. Ultimately, she proved that she truly is a triple threat and has a knack for comic delivery and acting!



9. Spears & Timberlake Break-Up — 2002

Spears and Timberlake surprised fans after breaking up in March of 2002, and both singers were interviewed about their split multiple times in the months following. In November of that year, Timberlake opened up about their tumultuous breakup in an interview with Barbara Walters.

“I remember when we decided we were going to go our separate ways, we sat down and I said to her, ‘If there’s ever a moment where you ever need me, you can rest assured that I will be there, because I love you as a person and I will always love you,'” he said, per Us Weekly. Timberlake alsopromised her that [he] wouldn’t say specifically why [they] broke up.”



Timberlake also came under fire after laughing when Walters asked about his sex life with Spears. In December of 2021, the “Toxic” singer detailed how difficult and memorable the breakup was for her, and how she could still recall the pain years later. “Something I never shared when I had that big breakup years ago was that I couldn’t talk afterwards,” she wrote on Instagram (in a since-deleted post). “I never spoke to anyone for a very long time,” she added.

In a 2003 interview with W Magazine, Spears explained how hurt she felt after Timberlake went on The Star & Buc Wild Morning Show in the previous year and revealed that Spears lost her virginity to him. “I’ve only slept with one person my whole life,” she said at the time, per Entertainment Weekly, adding that she did wait “two years into [her] relationship with Justin” to have sex.

In February of 2021, following the highly viewed Framing Britney Spears documentary (which highlighted Timberlake’s gross and unflattering comments about Spears) the actor responded to criticism from fans and apologized publicly to Spears.

10. Spears Kisses Madonna On MTV VMAs Stage — 2003

Throughout her career, Spears has often cited Madonna as a major inspiration and influence on her artistry and music. At the MTV Video Music Awards in 2003, Spears locked lips with her idol after the two sang and danced together on stage. The quick mid-performance kiss made headlines in the days following it, and Spears sat down for an interview with CNN at the time.

In the interview, the “Circus” singer said, “I didn’t know it was going to be that long and everything.” She added that she and Madonna decided to “just feel it out and see what happens” during the performance and that they thought of the idea while rehearsing for the show.

“I’ve never kissed a woman before,” Spears continued. When asked if she would ever do it again, Spears replied, “No, I would not do it,” but then went on, “Maybe with Madonna.” Years later in 2022, Spears delighted fans after she and the fellow pop legend recreated their famous kiss, this time at Spears’ wedding to longtime beau Sam Asghari.

Spears’ 2023 Plans

As seen on Spears’ Instagram account, the “Stronger” crooner is currently thriving after celebrating a full year of freedom from her conservatorship (that launched the #FreeBritney movement and garnered millions of supporters). From sweet photos with her husband to sultry pics showing off her toned figure, Spears seems happier than ever.




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The “Gimme More” artist will also soon celebrate the premiere of her upcoming Broadway show— Once Upon a One More Time— a new musical scored by a plethora of her beloved hits. The show will open at the Marquis Theatre in New York City on June 22, 2023, with preview performances beginning on May 13th.

In a statement, Spears opened up about her joy in sharing more about the project, which will include familiar Disney characters within it (picture Cinderella, Snow White and more singing Spears songs!)


“I’m so excited to have a musical with my songs — especially one that takes place in such a magical world filled with characters that I grew up on, who I love and adore,” Spears said in a statement about the show. “This is a dream come true for me!”