15 Britney Spears moments that prove she will always be a pop icon

The first CD I ever received as a gift in the early two thousands was Britney Spears’s Oops!… I Did It Again. My brother and I fought over her poster, my friends and I at ballet fought over her perfume, and the only thing we all agreed on was the choreography from the Toxic video and the diary of her relationship with Justin. Born on this day exactly 44 years ago, the pop icon delivered unforgettable music videos, spectacular performances and record breaking albums at the height of her career, shaping the pop landscape and inspiring generations to follow in her footsteps. Yet this historic success had a dark side as well. Her long public battles with the pressures of fame, media control and personal struggles culminated in a conservatorship that lasted almost 14 years and placed her life and finances under someone else’s control. In spite of everything, Britney remained a symbol of resilience and a figure who redefined power in pop culture, and her release in November 2021 marked a new beginning and a reminder that personal freedom and creative agency can be reclaimed.

To mark her birthday, we look back at 15 unforgettable moments from Britney Spears’s life and career.

The Mickey Mouse Club

In her memoir, she described The Mickey Mouse Club as “a real boot camp for the entertainment industry. Exhausting dance rehearsals, singing lessons, acting lessons, time in the recording studio and school in between everything.” She shared clothes with Christina Aguilera, spent time with Ryan Gosling and got kissed by Justin Timberlake during a game of Truth or Dare. “The show was, honestly, a childhood dream. Incredibly fun, especially for a kid like me. But at the same time, incredibly demanding,” she added.

Early performances

In her memoir, Britney points out that the start of her career in the nineties, with performances, “traveling with the dancers [and] goofing around with the girls,” was the most beautiful part of her youth. She explains that she was still under less public scrutiny and had more freedom to be playful and do what she loved. That early honing of her craft and dance skills is what allowed her to become an uncompromising performer once she reached global fame.

…Baby One More Time

Released in 1998, her debut single became an overnight hit. The most brilliant part is that much of the music video’s concept was her own idea. From the choreography to the school uniform, cute guys and loads of dance scenes, she came up with it all, according to the video’s director Nigel Dick. “All the wardrobe pieces in the video were bought at Kmart, and I was told none of them cost more than 17 dollars. Looking back, that is probably part of its charm.”

Cameo in Sabrina the Teenage Witch

A beloved nineties TV series, Sabrina the Teenage Witch was a major cultural touchstone for teenagers. Spears’s cameo in 1999, right as she was becoming a huge star, was an important moment in her rise. Melissa Joan Hart and Britney were the same age and spent a lot of time together during that period, becoming friends. Hart later appeared in the Drive Me Crazy music video, from the soundtrack of her film of the same name.

Relationship with Justin

Their relationship would later turn turbulent, not to mention the fact that Justin Timberlake used their painful breakup to build his own brand and damage hers. But there is no denying that when Britney and Justin first appeared together at the VMAs, fans were delighted. They became a beloved celebrity couple, with audiences and the media following their every move, especially their coordinated outfits, including the iconic denim look. Costume designer Steven Gerstein said, “It was like their prom. They had the idea and we did what they wanted, not the other way around. The rest is history.”

Photo: Getty Images

Hosting with Christina Aguilera at the MTV VMAs

The media often emphasized the fact that both came from The All-New Mickey Mouse Club and pitted them against each other in problematic ways. Their joint appearance, obviously staged, where they chatted charmingly and introduced Whitney Houston, created a huge buzz among fans. The two singers would later have a public feud, but also reconcile.

Grammy Awards performance

Nominated for the first time in 2000, Britney both performed and delivered a memorable act at the Grammys. It opened with a film of young Britney watching the ceremony and imagining herself on stage, then transitioned into a performance of From the Bottom of My Broken Heart and a remix of the classic …Baby One More Time, complete with impressive dance moves and a large group of backup dancers, including robots. It was a remarkable feat for such a young star.

Super Bowl performance

Rock and pop royalty Aerosmith and *NSYNC performed together at the 2001 Super Bowl Halftime Show. Then Britney Spears, Mary J. Blige and Nelly joined them on stage to perform Walk This Way. Spears and Timberlake, who were dating at the time, even walked together for a few steps, showing their chemistry on stage.

The Madonna kiss at the 2003 MTV VMAs

Three icons sharing one stage was already enough for a spectacle. Then Madonna kissed Spears live on stage, which shocked virtually everyone. Unfortunately, there was a wave of backlash, mostly directed at Britney. Christina Aguilera was also frustrated because her kiss with Madonna was ignored when the camera cut to Timberlake’s shocked reaction instead. Calling it a “cheap shot,” Aguilera said in a 2018 interview, “I saw the covers the next day. It was like, ‘Oh, I guess they left me out of that.’”

Photo: Getty Images

Creating her own fragrance

Technically, Britney created more than one fragrance. But her first perfume, in a sweet pink bottle, remained the ultimate status symbol of early two thousands teenage culture. Curious was reintroduced to fans and sold in a box set with her memoir The Woman In Me in October 2023.

Cameo in How I Met Your Mother

In the third season of How I Met Your Mother in 2008, Britney appeared as Abby, a receptionist. Ted goes to a dermatologist’s office to remove a tattoo and becomes interested in the doctor, while Abby becomes interested in him. He is completely unaware, so Abby briefly gets involved with Barney. Reportedly, Spears was a fan of the series and requested the cameo herself. Her appearance boosted ratings and the cast was impressed by her comedic talent.

MTV VMA Awards 2008

In 2007, Britney performed Gimme More at the VMAs. It was supposed to be her big comeback, but she appeared visibly nervous and insecure. She later admitted she was dealing with postpartum issues and felt pressured to perform. In 2008, she won Video of the Year, Best Female Video and Best Pop Video, all for Piece of Me, marking her big return. Still, she was not ready. Although fans supported her fully, the people around her did not.

Free Britney

The Free Britney movement began shortly after Spears was placed under a conservatorship in 2008, controlled by her father. Advocates raised concerns over the fact that despite the extreme restrictions, she was touring worldwide, releasing albums and working on TV projects. Her conservators decided whether she would work because she could not sign contracts on her own. She was legally not in control of her life. The New York Times documentary Framing Britney Spears helped turn the movement into a global conversation and exposed how powerless she was. In 2021, after court proceedings, the conservatorship was finally terminated.

A new beginning

When Spears married Sam Asghari in 2022, many hoped she had finally entered a healthy and stable relationship with someone who would treat her as she deserved. The pair met in 2016 on the set of the Slumber Party video, and Spears calls him “a gift from God” in her memoir and says she was “immediately smitten.” Even after their divorce in 2023, Asghari wished her the best: “I hope she takes over the world,” he said.

Photo: Getty Images

A chance to tell her story

In her 2023 memoir, Britney wrote with raw honesty about the tragedies in her life, from being chased by paparazzi at the peak of her fame, to being exploited and hurt by partners, to how misogyny demonized her and, of course, the conservatorship that forced her to work without consent, controlled every day of her life and left her with no means to defend herself. The book became one of the fastest selling nonfiction titles in history, and for good reason. Fans around the world celebrated the fact that Britney finally felt strong enough to tell her story on her own terms. P.S. Universal Pictures is officially preparing a biopic about her.