Cast
- Jena Malone as Mary Cummings, a quiet girl who attempts to help her gay ex-boyfriend, Dean, by giving him her virginity.
- Mandy Moore as Hilary Faye, the leader of the Christian Jewels and initially Mary's best friend. She is an extremely devout conservative Christian, though very self-righteous and overbearing, much to the annoyance of others. She reluctantly keeps her handicapped brother, Roland, on a tight leash.
- Macaulay Culkin as Roland, Hilary Faye's paraplegic brother. He fell out of a tree as a child, leaving him paralyzed from the waist down. Unlike his sister, he isn't really a Christian.
- Eva Amurri as Cassandra, the only Jewish girl to ever attend American Eagle. She is naturally rebellious and devious on the outside, but when she becomes friends with Mary and lovers with Roland, her true colors show in that she is actually very loyal and open.
- Patrick Fugit as Patrick Wheeler, the son of Pastor Skip, the school's principal.
- Elizabeth Thai as Veronica; adopted from Vietnam by a pair of missionaries, she is the third Christian Jewel.
- Chad Faust as Dean Withers, Mary's boyfriend at the beginning of the film. He comes out to Mary as gay.
- Martin Donovan as Pastor Skip Wheeler, the principal of American Eagle. A superficially pious and devout minister who is cheating on his wife, Pastor Skip tries to remain "young and cool".
- Heather Matarazzo as Tia; somewhat of an outsider in the beginning, Tia takes Mary's place in the Jewels when Mary is kicked out. Her father has a drinking problem which disturbs her deeply.
- Mary-Louise Parker as Lillian Cummings, Mary's mother, a widow from an early age.
- Canadian guitarist Dave Rosin Hedley (band) appears as the guitarist for the band playing in the prom scene.
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