Britney Spears' 15 Most Iconic Moments In Pop Culture History

Photo: Kevin Kane/Getty Images.
If Michael Jackson was the King of Pop, then Britney Spears is its princess. Sorry, Xtina, Katy Perry, and, yes, even you, T.Swift: Britney is the original royal pop star. Her meteoric ascent to chart-topping fame was followed by a tumultuous period in her personal life, which, many would argue, began in 2004 with her getting hitched to a childhood friend at a Vegas chapel for a grand total of 55 hours — followed by her marriage to Kevin Federline later that same year.
By all accounts, the Britney Spears we all fell in love with is alive and well today. Her lucrative Las Vegas residency, Britney: Piece of Me, kicked off in 2013 and will run until at least 2017. Early this month, she released her first app. She's been hard at work on a new album, which is rumored to drop later this year. On Sunday, Spears will receive the Millennium Award at the Billboard Music Awards, where she'll perform a medley of her greatest hits. In honor of the accolade, here are 15 of Britney Spears' most iconic pop culture moments. It's Britney, bitch.
Advertisement
1 of 15
"...Baby One More Time" (1998)

Oh, baby, baby. This was the single, music video, and album that started it all, folks. Back in '98, Britney broke onto the scene as an unknown singer with a killer voice — and a shockingly sexy image for a 16-year-old. The "Baby" video is now the pinnacle of the naughty Catholic school girl in our pop culture lexicon.
2 of 15
Britney + *NSYNC = Magic (1999)

At the 1999 MTV VMAs, the boy band sensation joined forces with the hottest new thing in pop with an epic mashup of "...Baby One More Time" and "Tearin' Up My Heart." A musical match made in heaven. And it became apparent that it was a romantic match, too. This was the year that pop's first It couple, Spears and Justin Timberlake, started dating.
Advertisement
3 of 15
Photo: Courtesy of Rolling Stone.
Her First Rolling Stone Cover (1999)

People are confounded by an overtly sexual 17-year-old girl and self-proclaimed virgin. That enticing tension is captured here in her first RS cover story, a veritable pop culture milestone. (Note the purple Teletubby.) "What’s the big deal?" she said at the time. "I have really strong morals, and just because I look sexy on the cover of Rolling Stone doesn’t mean I’m a naughty girl."
4 of 15
"Oops!...I Did It Again" (2000)

Had the world even seen a red, skintight latex bodysuit before the "Oops" video kicked off the new millennium with this sensual space jam? It features an ethereal Britney, moments of humor, and the sexiest astronaut, ever.
5 of 15
"Stronger" (2000)

The world didn't know what a dynamic pop force it was reckoning with until it saw Britney slay the choreography in the sleek video for this empowering anthem — with little more than a chair. And the game-changing minimalist concept was all her. “She said, 'I would like to dance in a chair and drive in a car and break up with [my] boyfriend,'" said director Joseph Kahn.
6 of 15
Photo: Jeffrey Mayer/WireImage.
All-Denim Everything (2001)

If there is one couples look that epitomizes the red-carpet travesties perpetrated by celebrities in the early 2000s, this is it. Spears and then-boyfriend Justin Timberlake wore matching denim ensembles to the American Music Awards, a show stolen by JT's COWBOY HAT MADE OUT OF JEANS.
7 of 15
"I'm A Slave 4 U" (2001)

Two words for you, people: Live python. A century from now, Britney's exotic spectacular will still be remembered as one of the most controversial MTV Video Music Awards performances of all time. The outrageous stunt riled up everyone from scandalized parents to animal-rights protesters (the performance featured several other live animals, including a white tiger). It also signified Britney's concentrated pivot from girl next door to wild thang.
Advertisement
8 of 15
Crossroads (2002)

Yes, haters, Crossroads makes the cut. Britney's big-screen debut didn't make any Best Movies of The Year lists, but it made a respectable $60 million at the box office and earned Brit an A for genre-crossover effort. Plus, how many pop singers can say they've starred alongside actors like Zoe Saldana in a film written by the great Shonda Rhimes (albeit pre-#TGIT) and helmed by the director behind Billy Madison?
9 of 15
Photo: Picture Perfect/REX/Shutterstock.
A Star On The Hollywood Walk Of Fame (2003)

It's a seminal moment in any artist's career. But at just 21 (and a mere five years into her career), Britney Spears became the youngest musician ever to receive the honor.
10 of 15
The Kiss (2003)

Remember that time Madonna locked lips with Britney and then Christina Aguilera at the MTV Movie Awards? Because literally everyone who was alive in 2003 does. The three divas belted out "Like A Virgin" in the least virginal bridal get-ups of all time. And then, they kissed and no one knew what to think. (OH MY GAWD WHAT ARE THEY, LESBIANS?!) 13 years and several experimental Miley Cyrus performances later, it would be NBD. But this is one onstage smooch we will never forget. (Also, the cutaway to JT's reaction: Priceless.)
11 of 15
That Big-Ass Pepsi Deal (2004)

Sorry, but it's a fact of modern life that being the face of a brand is a huge help when it comes to securing pop-icon status. The singer made millions on her contract with the soda company. All of the Britney Pepsi commercials were kind of amazing, but we especially love this epic Super Bowl ad featuring Brit, Beyoncé, and Pink as gladiator rock stars. (Britney, apparently unable to stay away from the Coca-Cola, was replaced by none other than Bey.)
12 of 15
"Toxic" (2005)

OMG, best video ever. We thought it then and we stand by it now. Secret Agent Britney exacts revenge on her scumbag boyfriend and bedazzles her naked body in a scandalizing video MTV deemed too racy to play any time but late-night. And the song nabbed the singer her only Grammy, ever. (I know, WTF?) Do yourself a favor and watch this gem again, 11 years later.
Advertisement
13 of 15
Britney and Kevin: Chaotic (2005)

"Can you handle our truth?" is the question Britney and then-husband Kevin Federline posed to the world with their five-episode reality show — a mashup of low-quality home videos presented as a candid portrait of their relationship. The world answered with a resounding "no."

Critics referred to the as a "totem to the pop singer's narcissism" that "evokes a vagina devouring everything in its path;" "a self-indulgent, mindless piece of drivel;" and "a visual assault of nauseating camera angles" that "makes Jessica [Simpson] and Nick [Lachey] look like Mensa candidates." But even pop culture fails can be iconic.
14 of 15
Photo: Courtesy of the Daily News.
The Shaved Head (2007)

You're right, Britney shaving her own head at a random Tarzana, CA, salon has nothing to do with her talent. But this shot represents the hideous underbelly of the pop culture pressure-cooker that churned out a severely unwell young woman — not to mention our culture's voracious appetite for putting pop goddesses on a pedestal, only to watch them with rabid fascination as they stumble from grace and into rehab.

Her personal struggles manifested as a public meltdown. This particular media free-for-all was just one point in Spears' erratic and horrific downward spiral that began years earlier, which included: A 55-hour marriage, hard partying, multiple trips to rehab, another divorce, ugly custody battles, drug use, child welfare investigations, multiple car accidents, and involuntary psychiatric commitment.
15 of 15
Circus (2008)

Britney embraced the circus around her and became its ringmaster — channeling the madness into a Ringling Brothers-worthy album and world tour. ("All eyes on me in the center of the ring just like a circus / When I crack that whip everybody gonna trip just like a circus.")

A full decade after her debut, Britney's sixth studio album dominated the charts upon its release at the end of a very rough couple of years. The release and elaborate tour, both critical and commercial successes, were hailed as her big comeback. Circus produced hits, including "Radar," "If U Seek Amy" (the best naughty phonetic double entendre, ever), and "Womanizer" — her first single to hit No. 1 on the Hot 100 since "...Baby One More Time."
Advertisement

More from Pop Culture