Anson Mount was initially reluctant to accept the role of Ben - finding the script to be "cheesy" and "lame" - but was encouraged by Robert De Niro, with whom he was working at the time on City by the Sea (2002). De Niro turned out to be a huge Britney Spears fan. They went over scenes from 'Crossroads' on breaks from 'City by the Sea,' with Mount reading his lines and De Niro reading Spears'.
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When Lucy's Dad is talking to Lucy in the hospital, a picture of Britney Spears can be seen on a copy of USA Today that a man is reading in the waiting room.
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The pictures in Lucy's locket are actual pictures of Britney Spears when she was younger.
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In the scene where Mimi, Lucy, and Kit are partying in the Louisiana Hotel room, you can hear Britney Spears accidentally shout "Zoe" at Kit, played by Zoe Saldana, when they are laughing about a dirty subject.
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Bowling for Soup, the band who features in the film and have 3 songs in the film, belong to Britney Spears' record company, Jive Records, as do *NSYNC (the band featuring Spears' then boyfriend Justin Timberlake) who also have a song that features in the film.
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At one point in the movie, the girls sing "Bye Bye Bye," which was a hit song by *NSYNC. This was an inside joke referencing the well-publicized romance between N'Sync member Justin Timberlake and Britney Spears.
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One of the highest grossing movies in Japan, due to Britney Spears' popularity there.
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The set used for the hospital scene is that from TV Series Scrubs (2001).
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Dan Aykroyd created a detailed back-story for his character and his life in the navy. He even had a friend draw a navy tattoo on his arm (which can be seen in the scene where he is working on the car in the garage).
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During the celebration scene in hotel room in New Orleans, the song that is playing on the radio which the girls danced to is entitled "Crazy Love" by Boomkat, A.K.A. Taryn Manning.
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No Coca-Cola products are ever used. Instead, Pepsi products are featured prominently, e.g. Mimi drinks from a Pepsi can in the hotel room after their karaoke win. Britney Spears, of course, endorses Pepsi-Cola.
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When Lucy gets out of the shower in the first hotel room, a bottle of Herbal Essences shampoo is visible inside the shower. Britney Spears endorses Herbal Essences shampoo.
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The Britney Spears songs in the film all went on to become singles and were featured on her third album, "Britney," which was released shortly before the film.
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The scene where the group stop to watch the sunset before camping is filmed in Red Rock Canyon outside Las Vegas
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Melissa Joan Hart was considered for the role of Mimi.
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Lucy's last name comes from casting director Kim Davis-Wagner.
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Britney Spears wears a Southern University T-shirt in the movie, and on its poster. However, Southern University is a predominantly African American school in Baton Rouge, La. The reason for this is because costumer Wendy Schecter found the shirt at an L.A. thrift store, she explained that: "Her character, Lucy, is a college-oriented girl." Not only was the snug shirt a perfect fit. But, Britney Spears is from Kentwood, La., which is just 75 miles away from the 17,000-student Southern's main campus. The school enjoyed the publicity. "We're tickled pink," said Chancellor Edward Jackson, who approved of the shirt's usage. "The fact that we're African-American makes little difference." The school's bookstore saw sales of Southern clothing items increase drastically as a result of this free publicity.
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Development on the film began in 2001, when Spears created a concept that was later expanded by writer Shonda Rhimes.
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The band Bowling for Soup is playing at the party the group attends.
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According to Kim Cattrall, the role of Lucy's mother was originally intended for Madonna.
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Kim Cattrall stated in a 2020 interview for Los Angeles Times she only accepted her role because she was very curious to meet Britney Spears.
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Was originally titled "What Friends Are For."
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The poem Lucy reads to Ben at the campsite are the lyrics to Britney Spears' song "Not a Girl, Not Yet a Woman"
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Ben's car is a Buick Skylark custom convertible.
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Dan Aykroyd would later admit the main reason for accepting the role of Lucy's father was that he wanted the opportunity to meet Britney Spears.
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The film features two future MCU actors: Zoe Saldana and a 13 year old Brie Larson, who played a minor role.
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If you don't count her cameo in Longshot (2001), then this film was Britney Spears' film and acting debut. It was also Katherine Boecher's debut.
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Jamie Lynn Spears's debut.
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This film was meant to be a star-making vehicle for Britney Spears, and begin her movie career. Though the film made money ultimately, it was critically panned for being a vanity project for Spears, killing any chance she had at an acting career.
Back when this film was released, comparisons were often drawn by critics of this film to Glitter (2001), a starring vehicle for Mariah Carey. Both were panned for being vanity projects that only existed to start an acting career for the singers, though unlike Carey's film, this one received slightly better reviews and actually made money at the box office, while Glitter (2001) was a box office bomb (though it is worth pointing out that Glitter (2001) had the unfortunate timing of being released theatrically in the same week of the 9/11 terrorist attacks).
In the original script for the film, Lucy was supposed to be profane and swear. Britney Spears ordered that the profanity be taken out of the script so as not to tarnish her image for the younger pre-teen viewers of the film.
It was initially rumored that Britney Spears would be guest starring on the sexually suggestive HBO series Sex and the City (1998), playing the niece of Kim Cattrall's character Samantha Jones. A spokesman for HBO denied the reports, saying no such negotiations ever took place. Ironically, Spears and Cattrall would actually collaborate in this film, with Cattrall only accepting the role of her mother because she wanted to meet Spears in person.
There were reports that Britney Spears, Taryn Manning, and Zoe Saldana did a topless scene that was cut from the final edit of the film. Manning denied these reports. According to her and the film's producer, Ann Carli, the "flashing" scene was filmed only from the neck up, and none of the three actresses involved was actually topless during the shoot.
According to reports, Britney Spears arrived an hour late for the British premiere of this film and snubbed fans who had been waiting for her to arrive.
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