Britney Spears' most outrageous VMAs moments: From Madonna kiss to 'naked' outfit

Britney Spears was a consistent performer, winner and presenter at the MTV VMAs for almost two decades - with plenty of scandals and mishaps landmarking her appearances.

Britney Spears

Britney Spears' striptease at the 2000 awards caused controversy (Image: GETTY)

As the 2023 VMAs get underway, Daily Express US delves into Britney Spears’ most outrageous appearances at one of music’s biggest awards shows throughout her sensational pop career. 

2000 - The ‘near-naked’ look

The 41-year-old made a splash at her second-ever VMA appearance when she performed a medley featuring her hit Oops..I Did It Again combined with The Rolling Stones’ Satisfaction, but the cover remix wasn’t what sparked a frenzy that evening. 

The singer started her performance in a sparkling pinstriped suit which slowly began to fall off as she continued singing. 

The audience and viewers at home thought they were witnessing a wardrobe malfunction of epic proportions as her trousers slipped down, exposing a part of her thigh and behind.

The then-18-year-old revealed it was somewhat intended as she quickly ripped off the tear-away items to reveal a nude-illusion outfit, with skin-tight pants and a bikini-styled top the same color as her skin.

Britney Spears

Britney's performance with a live python stirred a frenzy (Image: GETTY)

Britney’s “near-naked” moment became so iconic her nude-illusion outfit has been on display at the Rock and Roll Hall of Fame since the performance. 

2001 - The snake charmer

Undoubtedly one of Britney’s most notorious moments arrived at the 2001 VMAs when the singer brought out a special guest star for her I’m a Slave 4 U performance; an albino Burmese python.

Many theorized that it had been a plastic or puppeteered prop, but the Toxic singer recently opened up on the terror she felt performing with a live snake around her shoulders.  

She wrote on her Instagram last week: “One of my favorite performances was with an albino python. I still remember how scared I felt when I was handed this snake and took the stage!!!"

Britney Spears

Britney said she was 'blessed' with the opportunity to kiss Madonna (Image: GETTY)

She also noted that she’ll be opening up about the heart-racing performance in her tell-all memoir, The Woman in Me, which is set to be released next month. 

2003 - The three-way kiss

During a sensational performance with Madonna and Christina Aguilera, fans watching at home were treated to an up-close look as Britney and the Like A Virgin singer locked lips in a shocking moment on stage

The broadcast then switched to a view of Justin Timberlake, Britney’s former flame at the time, sitting in the audience as he watched the events unfold.

However, in reality, there was a far more scandalous affair unfolding on stage as Madonna also turned to Christina for a three-way smooch.

Britney Spears

Britney's 2007 performance was meant to mark her 'comeback (Image: GETTY)

Speaking to Entertainment Tonight after the performance, Britney admitted that the move “could cause controversy” but felt “blessed” for the “awesome” opportunity to kiss someone she’d looked up to for so long.

2007 - The fumble

During one of her most trying years, Britney was also given the responsibility of opening the 2007 VMAs, shortly after pictures of her shaving her head covered magazines and websites across the globe. 

She took to the stage performing Gimme More in a tiny black and metallic bikini but was visibly uncomfortable throughout the routine. 

While she looked unsteady on her feet in black stiletto boots and unsure of the dance, fans were mainly focused on the bizarre bright blue-coloured contacts giving the singer an other-worldly appearance. 

Britney Spears

Some viewers believed Britney and Miley Cyrus were feuding at the 2015 awards (Image: GETTY)

A source told People at the time that Britney had changed her outfit last minute and was “just plain nervous” as the performance was meant to mark her comeback following the scandalous year she had been having. 

The fumbling performance also earned the VMA host Sarah Silverman some backlash as her opening monologue featured punchlines aimed at the then-25-year-old, including calling her children “adorable mistakes”.

2015 - The Miley vs Nicki feud

In 2015, all eyes were on Miley Cyrus and Nicki Minaj as the rapper confronted the host at the end of her acceptance speech for the Best Hip Hop Video but Britney had also been seemingly dragged into the fray earlier in the evening. 

The mother-of-two was presenting the first award of the evening, with Miley introducing her as “my emergency contact and someone who always picks up when I call”. 

As cameras turned to Britney on the stage, the singer quipped: “Okay Miley, to be fair, I did think it was Taylor Swift who was calling me.”

Britney Spears

Britney ended her 2017 performance by awkwardly dodging a kiss from G-Eazy (Image: GETTY)

2016 - The frustration 

In what would become her final VMA performance to date, Britney took to the stage in 2016 alongside G-Eazy to perform a medley of her recent releases including Make Me and Me, Myself & I. 

As G-Eazy rapped his verses in both tracks, Britney stepped off stage for a quick wardrobe change and returned with a handheld microphone while the one on her headset she had used for the first half of the performance hung around her neck. 

They began singing the chorus together but soon confusion flooded Britney’s face as she kept glancing down at her microphone and by the end of her lines the singer was visibly frustrated as she pointed accusingly at her microphone and dropped her head in disappointment.

While the performance continued to be marred by technical difficulties, with Britney seen belting into the microphone at one point with very little of her vocals being heard through the speakers, fans were quick to slam the singer for lipsyncing and miming her performance. 

Would you like to receive news notifications from The Express?