Britney Spears' Most Iconic Moments

Publish date: 2024-06-28

If you weren't dancing around in your room in a belly shirt pretending to be Britney Spears in the '90s, were you even alive? From the moment the former Disney star stepped onto the scene with the now iconic "Baby One More Time" video, Spears has been a constant fixture of pop culture.  Just consider her relationship with *NSYNC frontman Justin Timberlake, that infamous kiss with Madonna at the MTV VMA's, and even the not so great year of 2007. In honor of Britney's 34th birthday today, we're taking a look back at some of her most standout moments—that can only be described as 'slaying it.' All hail the Princess of Pop. 

1) When she redefined the schoolgirl uniform. It's unclear how many private school girls got in trouble for tying their button-down shirts into a crop top after this video debuted, but I'm willing to bet the number was high. From the pom-pom pigtails to the belly shirts and hallway dance routine, we were all changed and the Britney revolution officially commenced. 

2) When she joined forces with *NSYNC for the ultimate performance at the 1999 MTV VMA's. It was the most epic joining of the two biggest forces in pop music at the time—and Britney slayed that choreography. 

3) When she made us all want to go out and buy a red latex bodysuit. The fashion piece that became suddenly collectible the minute the Oops I Did It Again video premiered. 

4) When she surprised everyone with her 1999 Rolling Stone cover. This was when we all learned that maybe she really was "not that innocent" with a sexy, slightly creepy shoot including baby dolls, Teletubbies and lingerie. Sexy, slaying-it Britney had officially arrived. 

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5) When she stripped down to a nude Dolce & Gabbana bodysuit at the 2000 MTV VMAs. Those abs. That hair flip. That belly ring. Those dance moves. 

6) When she and Justin Timberlake rocked those iconic denim red carpet looks. Has any other celebrity relationship ever topped this level of couple dressing? 

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7) When she made her acting debut in the Crossroads movie. Britney's starring role gave us all that "I'm Not A Girl Not Yet A Woman"-moment while also making us want to run away on a cross-country road trip with our BFFs. Still one of the biggest Oscar snubs of all time if you ask me. 

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8) When she joined forces with Pink and Beyonce for Pepsi's halftime commercial. And they all became the first pop stars to ever win a SuperBowl. 

10) When she performed "The Way You Make Me Feel" with The King of Pop. Michael Jackson and Britney were the performance pair you never knew you needed. 

11) When she famously locked lips with Madonna at the 2003 MTV VMAs. The Queen of Pop and the Princess of Pop united for one of the most memorable live performances of all time. 

12) When she overcame her fear of snakes in order to prove that she's a slave 4 u. The 2001 MTV VMAs performance that made us all want to do some sit-ups, buy a belly ring and tote around a reptile as an accessory. 

13) When she set a new standard with the "Toxic" video. Need we say anything else here? Peak Britney. 

14) When she showed us all how to handle a wardrobe malfunction like a boss. While on her Las Vegas residency tour, Britney reminded us all she's still got it while performing right through her wardrobe mishap. 

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Lauren Alexis Fisher is the Senior Editor at Cosmopolitan, overseeing digital content across fashion, lifestyle, beauty, sex, and culture. Previously, she was the Market Editor at Harper’s BAZAAR and has written for publications including WWD, Bustle, and W Magazine. When she’s not busy taste-testing her way through every dirty martini in New York, you can follow her on Instagram for bad jokes, good outfits, and annoying vacation pics. 

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