Watch Riding in Cars with Boys

Drew Barrymore stars in Riding In Cars With Boys as Bev Donofrio, a girl who comes of age in the 1960s, eventually transcending teenage pregnancy to become a successful writer. Co-starring Jams Woods, Brittany Murphy, Sara Gilbert, and Lorraine Bracco, it is directed by Penny Marshall. The movie opens in the early 1960s, when the main character, Bev Donofrio, is 15. Bev is an ambitious dreamer who longs to become a writer. She and best friend Fay (Murphy) attend a party one night and enjoy one too many drinks. Bev hooks up with a guy at the party, Ray (Steve Zahn), and later discovers she is pregnant. She wants to abort the pregnancy but repeatedly fails to go through with it. Ray learns of Bev's pregnancy and contemplates marrying her. He subsequently proposes, and Bev halfheartedly consents. Fay becomes pregnant with a girl, confessing the news to Bev on Bev's wedding day. Less than thrilled about their situations, the friends think positively of the future and look forward to getting on with their lives as mothers of little girls.

The girls both proceed to term, though they begin missing their old lives. They lament not staying in school, and they feel bad about missing prom. Bev and Ray have a little boy, whom they name Jason. Bev is disappointed, even jealous, that Fay gives birth to a girl, Amelia (eventually played by Maggie Gyllenhaal). Fay's husband leaves her; Bev demands Ray leave after his drug habit becomes utterly apparent. Growing up, Jason blames his mother for his absent father, and Beverly blames Jason for her misfortune.

Fay and Beverly begin selling dope to bring in cash. Jason tells his grandfather, a cop (Woods), who busts the two women. Fay's family posts bail but instructs Fay to take her son and move away, never to have contact with Bev again. Years later, Bev writes a memoir. She and Jason reconcile, and she and Jason make peace as well.