Britney Spears, Justin Timberlake & More Couples Who Attended the VMAs

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Over the past four decades, many unforgettable duos have graced the stage at the MTV Video Music Awards.

At the 2003 show, Madonna shared a kiss with both Britney Spears and Christina Aguilera. Kanye West was spotted carrying a bottle of Hennessy and taking the microphone from Taylor Swift during her 2009 acceptance speech. Beyoncé made headlines by revealing her pregnancy five months before giving birth to Blue Ivy in 2012, and Britney Spears created quite a stir when she brought an albino Burmese python named Banana with her for her iconic 2001 performance.

The pop star explained in her 2003 memoir, “The Woman In Me,” that she mentally encouraged herself, “Just dance, just use your legs and dance,” during a performance. However, what the audience didn’t realize was that as she was performing, a snake suddenly moved its head directly towards her face, emitting hisses.

At that instant, she expressed, “I was contemplating, ‘Are you genuinely doing this now? The serpent’s tongue is darting out at me, in this very moment. Indeed. Now. Fortunately, I managed to return it then.

She won’t deny it wasn’t her favorite moment; she’s not trying to hide it. 

And yet, it’s not entirely implausible that she and the serpent would grace the red carpet together at the legendary awards show. After all, celebrities such as Selena Gomez and Justin Bieber (she interviewed him during their relationship in 2011), Britney Spears with her partner Justin Timberlake, Jessica Simpson and Nick Lachey have all been snapped by photographers at this annual gathering.

However, it could be that the award for the least successful pair would potentially go to Christina Applegate and Brad Pitt. Before Applegate was married and had children, she was paired with Pitt who was yet to gain fame from movies like “Interview with the Vampire”. During the 1989 show, she confessed in a 2015 episode of “Watch What Happens Live” that she ended their relationship.

According to Sebastian Bach’s admission on the radio show “Elliot in the Morning,” he was once considered more attractive, or a “hotter catch,” during the ’80s compared to Brad Pitt. In simpler terms, the person who outshone Brad Pitt’s stylish ’80s hairstyle was none other than Sebastian Bach himself.

During a particular period, Sarah Jessica Parker was present alongside her then-boyfriend, Robert Downey Jr., while Cher cozied up with Richie Sambora just a year prior. Prior to stepping out on the VMAs red carpet on September 7th, take a stroll down memory lane and enjoy this nostalgic journey.

At the 2000 MTV VMAs, despite not sporting their famous denim ensembles, the reigning monarchs of pop music managed to thrill fans with their shared stage presence.

It wouldn’t be truthful of us to claim that we haven’t felt a small pang of nostalgia for this couple…their relationship ended in late 2017 after a six-year on-again, off-again period. Here they are at the 2011 MTV VMAs.

Speaking of denim, looks like these two paid homage to Britney and JT at the 2014 MTV VMAs.

Approximately two months prior to their breakup and ending their romantic journey, which was full of excitement and an engagement, the renowned pop star and the performer from Saturday Night Live attended the 2018 MTV Video Music Awards together on the red carpet as a couple for the first time.

For approximately two years, the ex-SNL cast member and Larry David’s child were romantically involved, but they separated in the year 2018. However, their relationship was publicly displayed at the MTV Video Music Awards in 2017.

As a devoted admirer, I’d like to mention that Miley Cyrus’ younger sibling and a renowned rapper walked their first red carpet together at the 2018 MTV Video Music Awards, just weeks into their relationship… only to part ways a few weeks later.

The love story between them was brief, lasting only three months up until October 2008. During this period, they managed to go on a date at the MTV Video Music Awards, where his bandmates, Nick Jonas and Kevin Jonas, were also present.

During the 2004 MTV VMA red carpet event, their body language suggested that they might have been permanently parting ways. They appeared together at the 2005 show as well, but their relationship ended a year after that amicable encounter.

Prior to her romance with Robert Pattinson from the “Twilight” series, the actress (now married to screenwriter Dylan Meyer) was in a relationship with her co-star from the film “Speak”. They made a public appearance together at the 2008 MTV Video Music Awards.

In the same year, 2014, the model and the rapper jointly went to the MTV Video Music Awards (VMAs). However, a month later, she initiated the divorce proceedings.

In 2006, before his marriage to Kim Kardashian, Kanye had been engaged to another fashion designer. They both attended the MTV VMAs in 2007, and they ended their six-year relationship the following year.

Prior to the musician being romantically involved with Priyanka Chopra and Christian McCaffrey being paired together, they appeared as a couple at the 2014 event.

In 2014, the rapper was accompanied by her boyfriend at the MTV Video Music Awards. Exactly a year after, they became engaged, but called it quits in 2016.

It was getting a bit “Hot In Herre” when Longoria posed with the musician at the 2005 event. 

A year prior to ending their two-year relationship, Kanye West and his girlfriend attended the 2009 concert where he briefly borrowed Taylor Swift’s microphone. After that, you’re welcome to continue scrolling.

In 2005, which is rumored to be the year they were dating, these two famous figures shared the screen in the movie “Elizabethtown” and made a dazzling appearance on the red carpet at the MTV Video Music Awards.

During the 1997 MTV Video Music Awards, these two individuals had already cast a spell of sorts. It was at this event that Apple delivered her notorious “the world is full of crap” acceptance speech.

While making their journey towards finding their lifelong partners, Simpson and Cabrera graced the 2004 MTV Video Music Awards.

In 2008, the star popped up at the award show again on the arm of her then-husband. 

In simpler terms, by today’s standards, their relationship feels outdated, but back in 2005 during the MTV Video Music Awards, they were known for leading extravagant lives as a couple.

This former Mr. and Mrs. made quite the splash on the MTV VMA red carpet in 1999. 

As a lifestyle aficionado, I’d like to share an intriguing tidbit from the past. Once upon a time, in the vibrant year of 1989, I found myself, as part of a new romantic duo, gracing the red carpet at the MTV Video Music Awards alongside the iconic musician once known as Bon Jovi’s guitarist. Unfortunately, our journey together didn’t last much longer, and we called it quits the following year.

In 2001, the actress was back at the iconic show with a new rock star. 

During the brief span of just under a year, this pair made an appearance on the 2008 MTV VMAs red carpet side by side. However, they parted ways about two months afterwards.

Prior to her marriage to Matthew Broderick, the actress from Sex and the City was dating the Avengers’ star. Their relationship spanning over seven years continued until 1991, and during that time, they appeared together at the 1990 MTV Video Music Awards.

According to the tale, these two individuals decided to go on a single date, but instead of choosing a conventional location, they opted for the 1989 MTV Video Music Awards as their backdrop. However, she abruptly ended the date to meet an unidentified man, and as a result, the duo never went out together again.

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2025-09-07 19:23