There are certain rules of etiquette for breaking up with someone, and from the sound of it,
Justin Timberlake broke some major ones when he ended things with Britney Spears more than
20 years ago.
At the height of her fame in the early 2000s, Britney Spears was widely regarded as among
the most popular pop stars of her time.
Every aspect of her life, personal and professional, became the subject of intense media scrutiny,
and her romantic relationships were no exception.
She and fellow pop superstar Justin Timberlake, who were both born in 1981 and first appeared
on TV together in the early '90s on "The Mickey Mouse Club."
They first started dating in 1999, right around the time both their careers took off.
However, the relationship did not last long.
It ended rather abruptly in March 2002.
"I think everyone has a side of their story, and, um, to make them feel a certain way."
The relatively brief relationship was an intense period for both of them.
Both Spears and Timberlake have moved on, but one person close to Spears revealed recently
how Timberlake supposedly dumped her, and sounds pretty shady.
In April 2022, Chris Applebaum, who directed "The Darkside Remix" music video for Spears'
2001 smash hit, "Overprotected," revealed on Instagram exactly how Timberlake did it:
by text.
Applebaum told the story of Spears' immediate reaction to receiving Timberlake's breakup
text, which happened during production for Applebaum's music video, which MTV notes was
filmed in Los Angeles the first weekend of March 2002.
The director wrote in his post,
"At some point during the 2nd shift [of shooting] Brit disappeared and I went to her trailer
to fetch her, only to discover her BF Justin had just broken up with her via text message."
He went on to say of himself and Spears,
"We sat on the floor of her trailer for a minute, talked it out, and then rallied.
I told her she should get out there & show Justin he made the biggest mistake of his
life."
He also added a note to anyone who may be contemplating a breakup:
"Let me recommend to any who reads this: don't break up via text!"
Spears would go on to be nominated for her sixth Grammy Award for "Overprotected," in
the category of best female pop vocal performance.
But even with that professional acclaim, Spears' world was clearly rocked by her breakup with
Timberlake.
The "Toxic" singer revealed in her 2023 memoir, "The Woman in Me,"
"When I say, devastated, I mean, I could barely speak for months.
Whenever anyone asked me about him, all I can do is cry.
I don't know if I was clinically in shock, but it felt that way."
The actual text that Timberlake sent the singer has long been a mystery, but in October 2023,
just on the heels of Spears' memoir release, Applebaum revealed the harsh way Timberlake
called it quits.
According to Page Six, it came down to two words.
Applebaum explained that upon visiting Spears' trailer, the pop star said she couldn't believe
what she was reading, and then showed the director the text.
The two-word message blared through the screen, simply saying, "It's over!!!"
Naturally, rumors began to spread about Timberlake and Spears' breakup almost as soon as it happened,
and they were only bolstered by Timerlake's song, "Cry Me a River," which was released
later that year.
The song's music video featured Timberlake catching his girlfriend, a Spears lookalike,
walking hand-in-hand with another man, understandably fueling rumors that Spears was unfaithful
to him.
Though he denied at the time that the woman in the video or the song were based on Spears,
he and his producer, Timbaland, later acknowledged on an "E! True Hollywood Story" episode that
they, in fact, were.
"I walked into the studio and he could tell that I was visibly angry."
But in the nearly two decades since, the Spears and Timberlake seem to have made peace.
"Britney recently said she wants to collaborate with you.
Would you ever do it?"
"She did?
Sure!"
In June 2021, Timberlake spoke out in support of Spears during her controversial conservatorship
battle with her father, which ended in its termination.
Shortly after court audio was released of Spears publicly acknowledging her disdain
for the conservatorship for the first time, Timberlake posted his support on X, formerly
known as Twitter, writing,
"After what we saw today, we should all be supporting Britney at this time.
Regardless of our past, good and bad ... what's happening to her is just not right."