The film stars Britney Spears, Anson Mount, Zoe Saldana, Taryn Manning, Kim Cattrall, and Dan Aykroyd.

Spears's third studio album Britney (2001) was promoted as the soundtrack to the film, in addition to Crossroads (Music from the Major Motion Picture).

[4][5] As children growing up in a small Georgia town, Lucy, Kit, and Mimi bury a "wish box" and vow to dig it up on the night of their high school graduation.

However, as the trio grows up, their friendship fades: Lucy becomes the introverted valedictorian, Kit becomes the most popular girl in school, and Mimi becomes an outcast from the trailer park facing teenage pregnancy.

Kit is going to see her fiancé who is a student at University of California, Los Angeles (UCLA), and Lucy is going to find her mother in Tucson, Arizona.

During the trip, the car breaks down in Louisiana and, with little money, Mimi suggests that they sing karaoke at a New Orleans bar for tips.

While staying at a motel in Alabama, Kit tells Lucy and Mimi that she heard a rumor about Ben going to jail for killing a guy.

Uneasy for most of the trip, the girls finally confront Ben about the rumor, who reveals that he actually went to jail for driving his stepsister across state lines without parental consent because his stepfather was abusing her.

She, Kit, and Mimi head to the audition with Ben and receive a standing ovation for their performance of her song, "I'm Not a Girl, Not Yet a Woman".

"[8] A press conference was held during the Marché International du Disque et de l'Edition Musicale (MIDEM) in Cannes, France, on January 19, 2002, where Spears also premiered the film.

[9] Filming for Crossroads initiated in March 2001 in New Orleans, Metairie, Baton Rouge, and Tangipahoa Parish, Louisiana, near Spears' hometown.

"[11] Justin Long, who plays one of Lucy's best friends from high school, thought that Crossroads is "like a road trip buddy movie for girls.

"[12] Anson Mount revealed that before he took the role of Ben, he was on the set of the film City by the Sea with actor Robert De Niro.

[17] Audiences surveyed by CinemaScore gave the film a grade "B" on scale of A to F.[18] John Anderson of Los Angeles Times commented "Spears acquits herself as well as anyone might, in a movie as contrived and lazy as this one".

[20] Lisa Schwarzbaum of Entertainment Weekly gave the film a positive review, commenting Crossroads "not only makes excellent use of the singer's sweetly coltish acting abilities, but it also promotes a standardized set of sturdy values with none of Mariah Carey's desperate Glitter, or any of Mandy Moore's gummy pap in A Walk to Remember".

[22] Robert K. Elder of the Chicago Tribune said "Spears delivers a performance with the same sincerity she invests into a Pepsi commercial, only this film contains twice the sugary calories",[23] while New York Daily News writer Elizabeth Weitzman noted, "Here's what Crossroads does not have: Cohesive direction from Tamra Davis, intelligent dialogue, a comprehensible plot".

[24] Maitland McDonagh of TV Guide commented that "the film's mealy-mouthed messages about feminine empowerment will almost certainly fall on deaf ears, since even 11-year-olds know Spears's power resides largely in her taut torso".

[30] In 2021, Pamela Hutchinson wrote a critical reassessment in The Guardian, noting that prior negative reviews had "recoiled at the film's savvy as a star vehicle – the way it builds up and reinforces Spears's commercial persona, from her virginity to her work ethic."

Hutchinson argued "Crossroads was designed to represent what Britney Spears meant to her young fans, a hand to hold through the minefield of growing up.