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Justin Timberlake & Britney Spears: Everything You Need to Know

The most iconic pop culture relationship of all time
Instagram @britneyjustinn

Britney Spears. Justin Timberlake.

Two of the biggest names in pop music and, for a short time, the most iconic couple the world had ever seen. No disrespect to Jessica Biel (Justin’s wife of seven years) or Sam Asghari (Britney’s hunky personal trainer boyfriend), but we’re here to dive right in and relive Britney Spears and Justin Timberlake’s relationship.

1. The All-New Mickey Mouse Club

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Reruns of variety show The Mickey Mouse Club started airing on the Disney Channel in 1983, but studio executives felt that the reruns were too dated for their audience, especially as these reruns were still in black and white. The executives created an entirely new version of The Mickey Mouse Club instead, and between 1989-1994 The All-New Mickey Mouse Club ran on televisions across America. This version of the variety show is famous because many of the child stars went on to be extremely successful. Christina Aguilera and Ryan Gosling had regular appearances, as did a young Britney Spears and Justin Timberlake. The young stars first met around the ages of 11 or 12, and were childhood friends before they began dating. Justin would be Britney’s first ever kiss *swoon*

2. 1998 – The Romance Begins

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In 1998, Justin’s boy band NSYNC embarked on their second concert tour. The tour, sometimes called the Second II None Tour or the Ain’t No Stopping Us Now Tour, lasted 18 months and guess who was billed as one of the supporting acts? That’s right, none other than Britney Spears! Spending time together touring North America as young adults and riding high on the success of their burgeoning careers, Britney and Justin began dating.

Video: Britney and Justin win The Teen Choice ‘Hotties’ Award

3. 1998 – 2002 The Golden Years

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Britney and Justin would date for four years. Within that time, Britney would become the best-selling teenage artist of all time with her smash-hit albums …Baby One More Time (1999) and Oops, I Did It Again (2000). Justin, the youngest member of NSYNC, was performing in one of the best-selling boybands of all time as a lead vocalist. Sure, his hair looked like 2-minute noodles, but at the time we were loving it!

Don’t worry Justin, we’ve all changed since the 90s. But back to the romance – Brit and JT quickly became America’s sweethearts. Britney had long been a poster girl for abstinence, citing her faith and her desire to find the right partner as her reasons for choosing to stay celibate. She spoke openly about the challenges of abstinence for young people on Oprah back in 2002 in the wake of her movie Crossroads being released.

Britney would later admit to W Magazine that she had changed her mind and slept with Justin. “I’ve only slept with one person my whole life,” she told the magazine. “It was two years into my relationship with Justin, and I thought he was the one.” We truly believe that Britney thought her and Justin would be together forever, because why else would they have felt that it was ok to show up to the 2001 American Music Awards twinning in double denim?

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Even though they wore this fashion monstrosity, Britney and Justin won our hearts as a celebrity couple because of how fresh and wholesome they seemed. Justin wore ‘JT Loves BS’ t-shirts during his Pop Odyssey World Tour, Justin was by Brit’s side at the Crossroads premiere.

Video: Justin surprises Britney live on camera

Heck, they even had basketball shirts made up with their nicknames, Pinky and Stinky, printed on them! But sadly, Justin wasn’t destined to be the one for Britney. The couple split abruptly in 2002, surrounded by rumours that Britney had cheated on Justin with her choreographer Wade Robson. The break-up was big news. No one could get a straight answer out of either Britney or Justin about why they had decided to go their separate ways and if the cheating rumours were true. Justin expertly dodged Barbara Walters questions when she sat down to interview him in his new home 5 months after the split. 

Video: Justin Timberlake is interviewed by Barbara Walters

“I remember when we decided we were going to go our separate ways, we sat down and I said to her, ‘If there’s ever a moment where you ever need me, you can rest assured that I will be there, because I love you as a person and I will always love you.” Justin said in the interviews. “But I also said, ‘Look, no matter what we say at this point people are going to speculate things, and I could really get myself in horrible position if I was to say something and somebody misinterpreted, because that happens all the time.’ And I promised her that I wouldn’t say specifically why we broke up.”

This was all well and good – but soon things got ugly.

3. Cry Me A River (2002)

Justin dropped this absolute banger in 2002, and it pretty much says everything but “You cheated on me Britney and I’m extremely salty about it.” The video clip shows Justin in his ex’s home, filming himself with another girl in their former bed, waiting until his ex (who is a dead-ringer for Britney) arrives home and then following her undetected around the house. If that doesn’t convince you who the song is aimed at, check out the lyrics: 

“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?”

4. Everytime (2003)

Britney allegedly replied to Justin via her song Everytime, a gentler ballad that seems to express ample regret and sadness.

“I may have made it rain/ Please forgive me/ My weakness caused you pain/And this song’s my sorry/ At night I pray/ That soon your face will fade away”
The underlying Everytime meaning is clear as day – Brit was sorry that she had somehow hurt Justin. On top of that, people still aren’t over Britney’s very public plea to Alyssa Milano, who started dating Justin months after his split with Brit. That’s one way to get your message across!
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And let’s not forget the time Britney, Madonna and Christina Aguilera kissed at the 2003 VMA’s. Cut to Justin’s reaction…

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Message received loud and clear. Britney was way past feeling sorry for her ex and was ready to move on too.

5. Justin and Britney’s best duets

They may have broken up over a decade ago, but we can still enjoy their greatest musical moments.

Justin and Britney sing ‘I Feel For You‘ on The All-New Mickey Mouse Club

Britney and Justin sing ‘I’ll Take You There’ on The All-New Mickey Mouse Club

Britney opens for NSYNC whilst on tour in 1998

The 2001 Super Bowl Half-Time Show that included Britney, NSYNC and Aerosmith

6. Team Britney or Team Justin?

Brit and JT split up so long ago that it would be pointless to pick a side. The most important thing is both superstars are currently leading happy lives with their respective partners and families. Britney’s father has been seriously unwell of late and, after nearly losing her Dad, Britney has announced that she has checked into a wellness facility to help her with the emotional stress that she’s been through. We wish her a speedy recovery.

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