Kerry Washington's first major role. She was working as a substitute teacher at the time, and paid so little for the film that she had to return to that job. Consequently she switched to only elementary school positions because high school students would show up to "watch Chenille teach French."
Director Thomas Carter cast Julia Stiles in the role of Sara after seeing her "table dance" in 10 cose che odio di te (1999).
On Ellen: The Ellen DeGeneres Show (2003), Kerry Washington revealed that she saved her earnings from this film to buy her first laptop.
The film makers originally wanted to film at Mount Assisi Academy, an all-girls Catholic school in Lemont. When they asked the school if they could remove the religious decorations, the president of the school refused.
Made $27,526,443 its opening weekend, the largest opening ever for the Martin Luther King, Jr. holiday weekend.