Britney Spears and Justin Timberlake were the "it couple" of the early 2000s,
but their breakup might have been an even bigger deal than their relationship. Here
are the moments in these two pop stars' romance that will definitely turn some heads.
Britney Spears and Justin Timberlake first met when they were both cast on the Disney
Channel reboot of "The Mickey Mouse Club." At the time, both Spears and Timberlake were
just starting out on their individual roads to stardom — as just pre-teens.
"Let's talk about the Mickey Mouse club where you got your start which is turning
out to be this great training ground for a lot of people."
Spears wrote in her memoir, "The Woman in Me,"
"Being in the show was boot camp for the entertainment industry: extensive dance
rehearsals, singing lessons, acting classes, time in the recording studio, and school in between."
"I probably started dancing when I was like three years old."
"It's tough."
Although there were many other future big names on the cast — including Ryan
Gosling — Spears admitted that one person in particular caught her eye. She wrote,
"I quickly connected with a boy named Justin Timberlake."
It turns out that feelings between Justin Timberlake and Britney Spears were mutual when
they first met. They progressed forward like any other kids growing up in the '90s would;
they hung out with other friends, had sleepovers, and played games,
like Truth or Dare. In Spears's memoir, she actually revealed that her first kiss
with Timberlake happened years before they became boyfriend and girlfriend. Sure enough,
it took place during a game of Truth or Dare at a sleepover they both attended. She wrote,
"Someone dared Justin to kiss me. A Janet Jackson song was playing
in the background as he leaned in and kissed me."
As the years went on, Britney Spears and Justin Timberlake embarked on very
different journeys. Timberlake was linked with four other guys to create one of the
most popular boy bands ever — NSYNC — while Spears pursued a solo career.
NSYNC was headlining sold out shows all over the United States, and Spears was left trying
to find her own fan base while recording music and making small appearances. Then,
in 1998, Spears got an opportunity to head out on her first-ever tour ... opening for NSYNC.
It didn't take long for rumors about Spears's love life to start circulating—some fans thought
that she was dating Timberlake while others were convinced that she had a thing with
Lance Bass. Spears totally played coy about her personal life whenever she was asked,
saying she was focused on her music career. She joked to Rolling Stone in 1999,
"Overseas they say it's Nick Carter of Backstreet Boys. I have no feelings at all."
However, Timberlake and Spears later revealed that they had made it official before her
"...Baby One More Time" album was released in 1999. Spears and Timberlake kept their
romance quiet for a bit, but made things public at the 2000 MTV Video Music Awards.
In a 2001 interview with The Guardian,
Spears talked about the very first house that she owned since becoming famous, saying,
"I love showing off my house. I can't wait to start having dinner parties here."
But there was something even more surprising that came out of that interview aside from
Spears wanting to throw dinner parties at age 19: Her boyfriend also lived with her.
Perhaps it was the need for privacy or simply that Spears and Timberlake were joined at the hip,
but the two cohabitated in Spears' home whenever they weren't on the road. She told The Guardian,
"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."
Sadly, young love didn't stand the test of time — or temptation. For years,
people speculated that Britney Spears stepped out on Justin Timberlake,
hooking up with choreographer Wade Robson. In her 2023 memoir, Spears confirmed that very rumor.
"We were out one night and we went to a Spanish
bar. We danced and danced. I made out with him that night."
This was the first time that Spears had ever confirmed cheating on Timberlake,
though she also said that it wasn't exactly the end of their relationship. Spears wrote
that she told Timberlake what happened and the two stuck things out until they
eventually broke up in 2002. But that's not all the tea that Spears spilled in her book.
In "The Woman in Me," Spears claimed that Timberlake also cheated on her while they
were together. She didn't name the person who he cheated with because that person has moved
on and has a family, and Spears clarified that she didn't want to cause any unnecessary issues.
After the split with Britney Spears in 2002, Timberlake channeled that heartbreak into his
music and released "Cry Me a River" later that year. The lyrics were about a tumultuous breakup
and gave fans a peek into Timberlake's failed relationship with Spears. The track was an
instant hit for Timberlake and ended up being one of his most popular singles of all time.
However, the song itself wasn't what really got people talking. As if Timberlake needed
to make it clear who "Cry Me a River" was about, he went the extra mile to really
drive it home. The music video for the song featured a Spears look-alike that
had the Internet in an utter frenzy. After the track's release, Spears did what any
other pop star ex-girlfriend would do in this situation: she responded with a song of her own.
In many ways, Britney Spears took the high road when she responded to "Cry Me
a River." It took a couple of years, but in May 2004, Spears released the single,
"Everytime," one of the first songs that she had ever written herself. The ballad
is about lost love that offers a message to a special someone,
and fans have been led to believe that the track is a direct response to Timberlake's song.
In a 2004 interview with MTV, Spears explained her intention behind the song's meaning.
"It's about heartbreak, it's about your first love,
your first true love. That's something all people can relate to, because you all have
that first love that you think you're going to be with the rest of your life."
Perhaps one of the biggest bombshells to come out of Britney Spears's 2023 memoir was that
she was pregnant with Justin Timberlake's baby while they were together. She wrote,
"It was a surprise, but for me, it wasn't a tragedy ... Justin definitely wasn't happy about
the pregnancy. He said we weren't ready to have a baby in our lives, that we were way too young."
She went on to reveal that she and Timberlake made the
decision to terminate the pregnancy. Spears wrote,
"To this day, it's one of the most agonizing things I have ever experienced in my life."
Britney Spears's heartbreak following her split from Justin Timberlake
stayed with her for years. In Spears's interview with Diane Sawyer in 2003,
she passionately spoke about her past relationship with Timberlake.
"I was upset for a while. We both are really young and it was kind of waiting to happen."
She continued to say,
"I will always love him ... he is such a great person."
Spears isn't the only one that felt this way,
either. Timberlake told People in 2002 after the split.
"I feel like I'm in the middle of a soap opera. I honestly know what it's
like to have a broken heart. I love Britney, and I'll always love her."
It's no secret that both Britney Spears and Justin Timberlake had a
rough time in the aftermath of their split. In a 2006 interview with GQ,
Timberlake expressed that he was upset with his ex for not having his back. He said,
"I felt like she had a couple of opportunities to just sort of stick
up for me, and she didn't. Which is ﬁne. But at that time, you know, I fought back,
and that's the way I fought back. I used my mind. I came up with [Cry Me a River.]"
In 2011, Timberlake tried to explain what was so specific and unforgettable
about their relationship. He told Vanity Fair,
"I just don't think we were normal; there was nothing normal about our existence. We
spent way too much time being the biggest thing for teenyboppers."
Aside from not being "normal," Timberlake also said that he still wanted nothing but the absolute
best for his ex — who was basically on her world domination comeback tour. Years after shaving her
head and going after a member of the paparazzi with an umbrella, Spears had released "Femme
Fatale" and was at the top of her game once again. Interestingly, however, through everything she had
been through, Timberlake revealed that he didn't reach out to her once, telling Oprah in 2007,
"I haven't spoken to her in years."
"Really?"
"Yeah."
Britney Spears's romantic feelings for Justin Timberlake may be completely out
of sight these days, but that doesn't mean that she has any ill will toward him. In fact,
she actually gave him a shoutout on Instagram — and he responded. She posted a video of
herself dancing along to Timberlake's 2018 song, "Filthy," with the caption,
"This is my version of Snapchat or TikTok or whatever the cool thing
you're supposed to do these days. PS I know we had one of the world's biggest
breakups 20 years ago ... but hey the man is a genius!!!! Great song JT!!!!!"
In response, Timberlake popped up in the comments section of the post,
offering a crying with laughter emoji and three high-ten emoji. This marked
one of the very first public interactions Timberlake and Spears had since their split.
It seems that with time to mature and grow, Justin Timberlake reassessed his actions
towards Britney Spears back when they were dating and in the aftermath of their split. In 2021,
Timberlake issued a public apology to Spears by way of a candid upload to Instagram. In the post,
Timberlake expressed his regret over his actions with Spears as well as Janet Jackson,
who was practically exiled from the music industry after the wardrobe mishap at their
2004 Super Bowl performance. He explained that he came to understand the privileges
he has received in the industry simply for being a white man. Timberlake wrote,
"Because of my ignorance, I didn't recognize it for all that it was
while it was happening in my own life but I do not want to ever benefit from others
being pulled down again. I want to take accountability for my own missteps in all
of this as well as be part of a world that uplifts and supports. I care deeply about
the wellbeing of the people I love and have loved. I can do better and will do better."
Timberlake's words came in the middle of Spears's battle against her long-standing
conservatorship. The "Toxic" singer didn't respond to her ex's apology at the time.
Britney Spears spent over 13 years of her life living within the limitations of a conservatorship
that was controlled by her father, Jamie Spears. In 2021, Britney went to court in an effort to
convince a judge that she not only was capable of managing her own life, but to begin the process of
speaking out for herself after she revealed she was abused within the conservatorship,
forced to work, and even held against her will. After one of Spears's court appearances in June
2021, her ex-boyfriend released a statement to show his support. Timberlake tweeted,
"After what we saw today, we should all be supporting Britney at this time. Regardless of
our past, good and bad, and no matter how long ago it was ... what's happening to her is just
not right. No woman should ever be restricted from making decisions about her own body."
He continued in a thread,
"No one should EVER be held against their will ... or ever have to ask permission to
access everything they've worked so hard for. Jess and I send our love,
and our absolute support to Britney during this time. We hope the courts,
and her family make this right and let her live however she wants to live."
Spears's conservatorship was eventually terminated months later in November 2021.