From Yellow Pythons to ‘that’ Madonna Kiss: A Brief History of Britney’s Most Iconic Moments

Image via Edge Publicity
Words by Henry King O’Reilly

In the late nineties there was one name on the lips of every mainstream media outlet…Britney Spears. The pop superstar is one of music’s biggest names and is responsible for some of the nineties and noughties most defining, and controversial, moments.

Image from “…Baby One More Time” music video

The Music Video That Changed Everything

In 1998 Britney exploded onto the pop scene with one of the biggest songs in music history. “…Baby One More Time” is a celebrated song in its own right, but it becomes truly iconic when paired with its provocative video. Dressed controversially in a schoolgirl uniform, Britney transformed the way the media and 21st century culture looks at that outfit. Britney became infamous after this video and looked set on a path of non-stop stardom. Every girl wanted to be her, and every guy wanted to date her. She became an idol overnight and not many people can define a generation with the release of their first single. What sparked a lot of controversy, however, was just how young Britney was when she was performing very provocative and explicit dances. Britney was 16 when she appeared in the now famous music video with many people arguing that this was inappropriate behaviour for a child and highlighted how vulnerable Britney was about to become.  Despite the controversy there can be no doubt that the release of “…Baby One More Time” and its music video is one of the most defining moments in music history and a moment that will be a staple of the 190s for years to come.

Image via Getty Images

Oh Britney, What Were You Thinking…

Britney’s rollercoaster relationship with Justin Timberlake defined the height of her career. The chart-topping power couple took the media by storm even performing together with Aerosmith for their legendary song “Walk This Way” at the XXXV Superbowl Halftime performance. However, it was later in the year that this iconic moment took place. Britney and Justin rocked up to the 2001 AMAs taking matching outfits to the next level. Britney and Justin showed up in fully matching denim outfits with Britney in a floor length denim dress and Justin accompanying the look in a full denim suit, matched with a denim hat. While the look was bold and arguably a crime against fashion it cannot be argued that this look was one of the most defining of Britney’s public appearances. However, only one year later the Disney Channel co-stars split amid rumours that Britney had been cheating on Justin with choreographer Wade Robson. Despite the split this is surely one the most defining appearance of the couples short lived relationship

Image via Kevin Mazur/Getty Images

Snake Charmer

How on Earth do you manage to choreograph a live performance to a song titled “I’m a Slave 4 U.” Well, if your name is Britney Spears you rock up to the 2001 VMAs in your finest green bikini top and sparkly hotpants with a seven-foot albino python around your neck. Yes, you heard me right: a SEVEN-FOOT ALBINO PYTHON. While this may seem too extreme for a normal person with a trained professional waiting meters away, imagine doing it in front of the world’s press and millions watching live. Britney did all this despite having an iconic VMAs performance ever. However, over the years Britney has grown older and realised this performance may not have been the smartest decision, telling E! News in 2016 “It’s insane! Why did I do that? It’s so dumb!” If you’re still struggling to understand the insanity of this, imagine Miley Cyrus or Katy Perry rocking up to the VMAs in the same fashion. While it looks unlikely that we will ever see a repeat of the stunt, Britney’s shocking and exhilarating performance is one that will go down in award show history.

Image via Rolling Stone

Cover Star

1999 was a big year for Britney, releasing her debut album …Baby One More Time which rocketed straight to number 1. With all this newfound stardom came the attention of the mainstream media. This included many magazine covers, but none were more controversial than her 1999 cover on Rolling Stone. This cover of Rolling Stone saw Britney lay across a bed scantily clad holding a Teletubby (for literally no reason.) To make this even weirder Britney was only 17 at the time dressed in nothing but lingerie in extremely intimate and revealing photos. This rightfully received extreme backlash, mostly from enraged parents of Britney’s mostly teenage fanbase who believed that this was not appropriate viewing for their children. Even Britney’s own mother didn’t know what she was letting herself in for, appearing on The Today Show saying “We were in shock at what was going on, and we were in awe. We didn’t have any choice in the pictures.” Whether this cover was the right decision or not there can be no arguments that this was the start of a lifetime in the spotlight for Britney Spears.

*That* Madonna Kiss

Like a child seeing their parent cheering them on at Sports Day, Britney always goes out of her way to impress at the VMAs. Having walked out on stage with a live python around her neck two years earlier, this time Britney was planning on making the headlines in an equally shocking way. The show opened with the pop queen and Christine Aguilera performing a medley of the Material Girl’s greatest hits including “Like a Virgin” and “Hollywood”, however, it was not their singing that drew all the attention. During the performance, the queen of pop leaned in, sharing a kiss with Britney seen the world over. This image became one of, if not the most iconic image of the VMAs and showed the world that the women of pop weren’t just here to take part, they were here to take over.

Still looking for more 90s nostalgia? Check out our article on Spice Girls fashion here!

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