Britney Spears and Justin Timberlake: A complete history

Lets take a look back at one of the music world's most famous couples.
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Britney Spears and Justin Timberlake are undoubtedly two of the hottest stars of their generation. Both have had long and successful independent careers and now have their own families but once upon a time, Britney and Justin’s lives were closely connected.

WATCH BELOW: Justin Timberlake reveals he regrets THAT double denim moment with Britney Spears

Their relationship began as cute cast members of the American variety show The Mickey Mouse Club and later blossomed into romance.

Justin and Britney first met on the show when they were 10 or 11 years old, but it wasn’t until seven years later when sparks flew between the two Mouseketeers. Timberlake was then touring with his boy band NSYNC and Britney was the opening act.

The two would then start a high-profile relationship. They dated from 1998-2002, as both were becoming big musical stars and were definitely the music industry’s hottest ‘Royal’ Couple during that period.

Rumour has it that Justin was Britney’s first lover. The starry-eyed pop star was quoted as telling The Observer in 2001:

“When people get too personal it bothers me. But I’m not ashamed at all to say that I love him from the bottom of my heart. As far as love is concerned, with him, too much is not enough. He’s everything”.

Unfortunately, the fairy tale ended a year later. It was a sudden break up and it was reported that the cause of the split was that Britney cheated on Justin with choreographer Wade Robson.

Timberlake was quoted in an interview with The Telegraph soon after:

“The break-up was absolutely heartbreaking for me. I can’t just have meaningless relationships with women. I have to find miss right in order to have a relationship. There’s got to be that big moment when she comes along.”

Although their love affair is pop culture history now, here we recall some of the best moments of the Britney Spears Justin Timberlake relationship:

1. The 2001 Super Bowl Halftime Show

In 2001 the world got to see Justin and Britney perform live together at the Super Bowl Halftime Show. Justin sang a series of songs including ‘Bye, Bye, Bye’ with his boy band NSYNC and Britney showed up looking super cool in a football inspired sleeve, crop top and tight pants.

The two of them sang ‘Walk This Way’ with other great artists including Mary J. Blige, Nelly and rock group Aerosmith who had a monster hit in the 90’s with ‘I Don’t Want to Miss a Thing’. Some say that Halftime show was one of the greatest in recent Super Bowl memory, never to be replicated.

2. So in love

Back in the day, Justin and Britney were the picture-perfect example of a couple in the throes of young love. They wore matchy-matchy sports jerseys inscribed with Stinky (for him) and Pinky (for her) which were their nicknames for each other.

Justin sported JT loves BS shirts during his Pop Odyssey World Tour, gave her lots of jewellery and spelled out her name with rose petals during a birthday surprise. Britney, for her part, didn’t mince words when she told Oprah Winfrey: “I would love to be with him forever.” 

Matching Shirts
Stinky and Pinky in their happier days. (Credit: Getty)

3. The now famous denim date

Justin and Britney’s matching outfits are today’s version of #RelationshipGoals. Their most memorable matching outfits have become famous – think their twinning denim ensemble at the 2001 American Music Awards.

Their denim red carpet look is perhaps the most iconic of all Justin & Britney photos and a Belgian fashion brand even made a t-shirt out of it. Fast forward to 15 years later and Katy Perry paid tribute to the couple when she sported the same look in the 2014 MTV VMAs.

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Justin and Britney’s denim ensemble (Credit: Getty)

4Cry me a river

After three loved-up years together, everyone was expecting Justin and Britney to get engaged. In 2002, the lovestruck duo had a photoshoot with Hello Magazine and Justin’s family even joined in. Alas, by the time Hello came out with the feature, the pair had already broken up.

Friends said it all unraveled very suddenly. Rumours were rife that Justin hit the roof when he learned of Britney’s infidelity from the very guy she had a fling with. 

Justin dealt with his heartache in words – everything that happened is captured in his hit song ‘Cry Me A River’ which he wrote in the year following the breakup. The meaning of the song says it all and the video even featured a girl in a sports cap, which was Britney’s fashion trademark.

“You don’t have to say what you did I already know, I found out from him now there’s just no chance with you and me there’ll never be don’t it make you sad about it? You know that they say some things are better left unsaid It wasn’t like you only talked to him and you know it don’t act like you don’t know it and all of these things people told me keep messin’ with my head (messing’ with my head) should’ve picked up honesty then you may not have blown it”.

5. Britney replied with ‘Everytime’

Reports said Britney and her family were “mortified” that Justin got too personal with a song like ‘Cry Me A River.’ There could be no doubt that the song was about her. She wrote ‘Everytime’ in reply.

‘Everytime’ meaning

The song is definitely gentler and kinder, and there’s even a hint that she is pining for a lost love and asking for forgiveness.

The popstar worked on the song with her then backing vocalist Annet Artani who broke up with her boyfriend at the same time as Britney. ‘Everytime’ is a beautiful ballad which has a haunting element to it. It was released in 2004 and went as far as No. 15 in the Billboard Hot 100.

“I make believe that you are here It’s the only way I see clear what have I done you seem to move on easy and everytime I try to fly I fall without my wings I feel so small I guess I need you baby and everytime I see you in my dreams I see your face, you’re haunting me I guess I need you baby I may have made it rain please forgive me my weakness caused you pain And this song’s my sorry”

Even now there are still fans out there who would love to see a Justin and Britney reunion. There seems to be little prospect of that though as Justin is completely in love with his wife Jessica Biel and their son Silas.


As for Britney, its no secret that her life went on a downward spiral after her breakup with Justin. Although clearly devastated at the time she has since picked up the pieces, raising two boys and is making a successful comeback. 

These days she is dating personal trainer Sam Asghari.


Team Britney or Team Justin?

Young love can be careless and fickle. Some of us will always wonder “why would Britney do such a foolish thing, kiss another boy?” “…and why would Justin never forgive her, if it was love?”

It’s 2018 and 16 years since the cheating drama went down. We’re still hoping a Britney Spears Justin Timberlake reunion will come about, even if it’s just of the musical kind, like collaborating on a concert or a song. Oops they did it again?

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