4. The filmmakers cast relatively unknown actresses Taryn Manning and Zoe Saldana to play Spears’ on-screen best friends. Saldana even had to use her agent’s frequent flier miles to fight for the role in-person after bombing her taped audition.
5. Anson Mount was picked by Spears to play her on-screen love interest, though the actor didn’t initially have interest in the project. It was none other than his City By the Sea co-star Robert De Niro who convinced him to audition.
“I was reading [the script] between takes, and Bob came up to me and goes, ‘What are you doing?’ and so I said,’Errr, it’s this movie and Britney Spears is doing it, I’m not even sure if I’m going to do it, I’m just reading it,'” Mount said at a 2002 press conference. “And he goes, ‘Why not? She’s great.’ So I showed him the script, and he read Britney’s lines to my Ben.”
6. The main cast bonded while filming the road trip movie, with Rhimes describing Spears as “very cheerful, very fun.”
“I think it was so different from being on the road and doing concerts—being able to stay in one place and be with the same group of people all the time,” Rhimes explained to Vice in 2016. “It was the first time I think she had hung out with people her own age. When she was on the road, it was her and a team of people, but this was her, and Taryn, and Zoe, and Anson. They were all sort of the same age, and I think they had fun together.”