But there was another moment, again captured by a crush of photographers, that is, perhaps, more troubling.
The time was May 2006 and Spears has been descended upon by photographers outside of a Manhattan hotel as she struggled to juggle a cup in one hand with her then 8-month-old son Sean Preston in her arms.
She stumbled in the process and a later photo, taken through a window, shows her in tears as she holds her son, seemingly trying to shield the world from seeing her visibly upset.
It was a moment many headlines overlooked to instead focus on the fact that Spears almost dropped her infant child while trying to avoid aggressive photographers.
That image of a distraught young mother tugs deeper in the wake of the documentary “Framing Britney Spears,” which debuted in February and shed insight on some of the struggles Spears faced as the result of such intense — and often dangerous and sexist — media scrutiny.
In the years that have passed, Spears faced other stuggles and has gone on to new professional and personal success — all under the same blindingly bright spotlight. In the process, she’s paved a path for young women in entertainment who came after her, and shown the public we can do better.
‘A cautionary tale’
It compared a then-troubled Spears with an also then-troubled US economy.
“As disturbing as it may be, the saga of Britney Spears’s downfall serves pretty well as a cautionary tale for young American consumers, Warners wrote. “She started out as a cutesy, innocent little girl, playing it fast and loose by asking for us to hit her baby, one more time. Then, oops, she did it again! And so did we. Young Americans kept gobbling her up, a sign of things to come when savings rates would hit rock bottom a decade or so later.”
That comparison may feel like a stretch to some, until you realize what a commodity Spears was and was to become.
She ascended from child star on “The All-New Mickey Mouse Club” to teen superstar singer, who then had to manage a transition into an adulthood that included marriage, divorce, and motherhood in quick succession, along the way pulling in millions.
‘The pop music push’
When Spears donned a school girl uniform for the music video for her hit “Baby One More Time” in 1999 she was very quickly dubbed “The Princess of Pop.”
It was the year of the boy bands with 98 Degrees, Backstreet Boys and N’Sync scoring hits. And while girl groups like Destiny’s Child and TLC were also running up the charts, Spears brought something different with her girl next door who’s unafraid to be a little edgy image.
These days young women owning their sexuality and their agency is common place, but back then it was a scandal — made even more so by a now famous 1999 Rolling Stone magazine cover featuring Spears.
“In a distant demographic echo of the postwar baby boom, the American teen population has reached the kind of critical mass that makes the culture industry sit up and listen. Teen spending power is reshaping pop culture, filling our TV screens with teen dramas and our multiplexes with teen movies,” the article read. “It has also put a perky new beat on the pop charts, where the devotional vaporings of boy bands have vanquished the roiling rock angst of the early to mid-Nineties.”
And she kept showing up — in magazines, on the charts and in provocative music videos.
Spears walked in her sexual energy in songs like “Oops!… I Did It Again,” “Toxic” and “Gimme More,” so that later stars like Miley Cyrus, Selena Gomez, Demi Lovato, Ariana Grande and Camila Cabello could run.
‘Leave Britney alone’
With that power came plenty of criticism.
During the dark days of constant headlines about Spears spiraling, an event occurred that would itself help shape pop culture.
In 2007, a young man named Chris Crocker uploaded a video on YouTube in which he emotionally defended Spears after she was criticized for her MTV Video Music Awards performance that was deemed by some as lackluster.
He screamed “She’s a human” and took the media to task with a tearful “Leave Britney alone!”
Witherspoon said that while she also had her run-ins with paparazzi, she and fellow actor Jennifer Garner were labeled “good” by the media, while Spears, Paris Hilton and Lindsay Lohan and others were portrayed negatively.
From out of her darkness, Spears has actually shone a bright light.
There is much more awareness and discussion today about the damaging effects of fame on the mental health of artists. Her struggles have made it possible for others to be more open about their own.
Still, the hunger for information about what’s happening behind the scenes with Spears — by both her supporters and onlookers — has not ceased.
Spears has requested to address probate court about her conservatorship on Wednesday, and, perhaps, that will put some speculation about her well being to rest.
She deserves compassion. She’s earned it and it is as much a part of her legacy as her music.
And we are all the better for it if we take that lesson to heart.