“I was much more interested in the young woman that I met than the image that people had of her,” screenwriter Shonda Rhimes — who penned the script before her Grey’s Anatomy or Bridgerton fame — recalled to Vice’s Broadly in 2016 of the “Circus” songstress. “She was a person, and I don’t think anyone at the time was looking at her — because it’s such a misogynistic society — as a person. The idea that we could portray her as a three-dimensional young woman was interesting to me. To have mean-girled her and turned her into a caricature would have been a mistake.”
The film, directed by Tamra Davis, followed three high school graduates, played by Spears, Zoe Saldana and Taryn Manning, as they road tripped across the country from their Louisiana hometown to sunny Los Angeles for various personal and professional reasons. In the process, they each discover their own identities and deepen their friendship.
“I have not spoken to Britney in 10 years, but we had an amazing time on Crossroads,” the Orange Is the New Black alum — who played Mimi in the 2000s classic — exclusively told Us Weekly in September 2021. “We spent months in the car that we took ‘cross country’ sharing stories, joking, laughing and had a friendship for years, especially while filming. I wish her only the best and am so happy about the progress of this week [amid her conservatorship case]. Nothing but love for Brit!”
“I just remember [Britney] being so nice,” Long, who played Lucy’s lab partner Henry in the film — the one her character attempted to lose her virginity to — told Us in May 2020. “She just seemed, like, such a down-to-earth [person]. I remember being so disarmed by how normal she seemed. It was at the height of her fame, and, like, everyone else, I was inundated by images of her. She was so popular, so famous.”
The Accepted actor added: “You always just sort of assume that [fame] changes people, or they act, I don’t know, larger than life. They act in a grandiose way — and she really didn’t. She was just really, really sweet and kind of normal. That’s what I remember.”
The film, which featured Spears’ vocals on “I’m Not a Girl, Not Yet a Woman” and her cover of “I Love Rock ’n’ Roll,” celebrated its 20th anniversary in February 2022.
“I think there was probably more money in the music than there was in the film,” Davis told Variety at the time of its milestone anniversary. “But I also think it took some of the pressure off. We wanted to make this cool, indie, road trip chick flick and not try to be all polished and puffy.”
She continued: “I know how much Crossroads meant to [Britney] — she’s told me and she’s told [producer] Ann Carli that it was one of the most incredible experiences and very impactful months in her life.”
Scroll below to see what the Crossroads cast has been up to since the flick was made: