In 1961 eleven-year-old Beverly "Bev" Donofrio (Mika Boorem) and her father Leonard (James Woods) are preparing for Christmas when Leonard asks Bev what she wants this year for Christmas. Bev says she wants a bra in order to get the attention of a boy she likes. Leonard tells his daughter that she is too young to be thinking about boys, and ends the conversation. Four years later in 1965, Bev (Drew Barrymore) is now an intelligent, but naïve teenager. Her dream is to go to college in New York and become a writer. She and two friends Fay (Brittany Murphy) and Tina (Sara Gilbert) attend a party one fateful evening where Fay finds her older boyfriend Bobby (Desmond Harrington), who is about to be deployed to Vietnam, while Bev gives a love letter to a popular football player named Sky. Sky reads the contents of the letter aloud to his buddies, and they laugh at her. Bev flees to the bathroom, where she is consoled by a friendly stranger named Ray (Steve Zahn). Ray defends Bev's honor and fights with Sky. They are chased from the party and joined by Fay and Bobby during their quick exit. The four go to a lookout where Bobby and Fay have sex in the backseat. Bev is overcome by Ray's kindness and also has sex with him. Leonard, who is a police officer, drives up and brings them to the police station, where Bev claims that they only kissed.
Sometime later, Bev discovers that she is pregnant. She tells Ray, who proposes, but Bev is reluctant to get married. She admits her pregnancy to her parents, who are scandalized by her refusal to get married. Bev hastily agrees to a wedding. At the reception, Bev is upset, because everyone is avoiding her, prompting Fay to publicly announce that she is also pregnant. Afterwards, Fay explains to Bev that her father wanted her to put the baby up for adoption, but she and Bobby will be getting married instead. The two girls, although initially upset, celebrate the fact they will be mothers together.
As the months go by, the girls realize they are missing out on three things: their childhood, prom, and an education. Bev gives birth to a son, Jason, whereas Fay has a daughter, Amelia. Bev is dissatisfied with her married life and continues to pursue her education. When Jason (Logan Arens) is three, she wins the chance for a college scholarship, but her interview goes badly when she is forced to take Jason along. The interviewer praises Bev's writings, but informs her that she will not get the scholarship, because the school fears that she has too many distractions. Later, Fay confides in Bev that she and Bobby are getting divorced, because he met another woman while stationed in Hawaii. To cheer themselves up, Bev and Fay take Ray's hallucinogenic mushrooms. Bev tells Fay that she's not sure if she loves Jason, because she's had to give up so many things for him. When Jason (Cody Arens) almost drowns in Fay's pool, Bev vows to be more attentive to him.
On Jason's seventh birthday, several people from Bev's high school show up to his party: old friend Tina is now engaged and going to NYU; and Tommy, who had a crush on Bev, just graduated from Berkeley and is going to pursue a Master's degree. He suggests that Bev move her family to California and pursue her education there, since the state offers financial aid. Ray agrees to the plan, but on the day they are supposed to leave, he goes missing. Bev's mother calls Bev to their house, where Ray is. Ray confesses that he is a heroin addict and spent their savings on drugs. Bev tries to help him detox, but Ray sneaks out while she is sleeping to get more drugs. When he returns, he tells Bev that it's impossible for him to quit. Bev decides that since Ray can't quit, he should leave the family instead. Ray agrees and Jason attempts to chase after him. He tells Bev that he hates her for making Ray leave.
Two years later, Bev and Fay still want to go to California, so they agree to let one of Ray's friends, Lizard, use Bev's oven so he can dry out weed. Jason (Logan Lerman) tells Leonard who arrests the group. Fay's brother bails them out, but uses their savings for New York to do so. Additionally, Fay reveals that her brother only agreed to bail her out if she moved with him to Arizona and cut off contact with Bev. Jason confesses he was the one who got them arrested and Beverly harshly tells him off that he ruined their lives and it's his fault Fay and Amelia moved away.
In the present day (1985), Beverly and Jason (played as an adult by Adam Garcia) are driving to see Ray. Bev has finally achieved her dream of publishing a memoir and since most of her book focuses on her life with Ray, she needs him to sign a waiver or else her book will not be published. Jason tells Bev that he wants to transfer from NYU to Indianapolis, but Bev refuses to let him, saying that he is getting the education that she never could. Jason calls his girlfriend Amelia (played as an adult by Maggie Gyllenhaal) and delivers the bad news. Amelia assures him that she is not angry, but worries that she can't make him happy like his mother can. Jason and Beverly finally arrive at Ray's trailer. They explain why they are there. Ray's wife, Shirley (Rosie Perez), tells him not to sign it and demands $100,000. Outraged, Beverly screams at him that she'll never forgive him and storms out. Jason follows her and calls her selfish for only caring about her book when he finally got to see his father again. He accuses her of being a bad mother and she storms off.
Ray comes outside and has a heart to heart with Jason. He reveals that leaving was the best thing he could have done for Jason and he believes it's the only reason Jason turned out to be a nice man. He secretly passes Jason the signed papers to avoid angering his wife. Jason finds Bev and they get into another argument. She insists that she was a great mother, because she sacrificed everything for him. Jason reveals that he wants to transfer to be with Amelia and apologizes to Bev for ruining her life. Bev softens and tells Jason that she is proud of him and thinks of him as the best thing in her life, and that Jason never ruined her life and she holds herself responsible for her mistakes and poor choices and she never meant to blame Jason for them. She gives him her blessing to transfer and gives him her car to drive to Indiana.
Beverly is forced to call Leonard for a ride and she complains to him how Jason blames her for everything wrong in his life. She then realizes that she has done the same to her father and together they sing a song from her childhood as they drive away.Drew Barrymore as Beverly Ann "Bev" Donofrio
Mika Boorem as Bev Donofrio, age 11
Marisa Ryan as Janet Donofrio
Olivia Morgan Scheck as Janet Donofrio, age 12
Celine Marget as Janet Donofrio, age 8
Steve Zahn as Raymond "Ray" Hasek
Brittany Murphy as Fay Forrester
Adam Garcia as Jason Hasek-Donofrio
Joseph M. Cannizaro as Jason Hasek (newborn)
Noah Hartwick as Jason Hasek (newborn)
Briana Tilden as Jason Hasek (baby)
Skye Arens as Jason Hasek, age 1
Patrick and Robert Salerno as Jason Hasek, age 2
Logan Arens as Jason Hasek, age 3
Harley Richards as Jason Hasek, age 7
Logan Lerman as Jason Hasek, age 9
Lorraine Bracco as Mrs. Teresa Donofrio
James Woods as Mr. Leonard Donofrio
Maggie Gyllenhaal as Amelia
Samantha Reale as Amelia, age 3
Samantha Lucier as Amelia, age 7
Skye McCole Bartusiak as Amelia, age 9
Rosie Perez as Shirley Perro-Hasek
Desmond Harrington as Bobby
Sara Gilbert as Tina Barr
Peter Facinelli as Tommy Butcher
The film received mixed reviews. It currently holds a 49% rating on Rotten Tomatoes based on 109 reviews. Roger Ebert gave the film three out of four stars and wrote, "A film like this is refreshing and startling in the way it cuts loose from formula and shows us confused lives we recognize ... This movie is closer to the truth: A lot depends on what happens to you, and then a lot depends on how you let it affect you". In his review for The New York Times, Stephen Holden praised Steve Zahn's performance: "It is hard to imagine what Riding in Cars With Boys would have been without Mr. Zahn's brilliantly nuanced and sympathetic portrayal of Ray, who goes through more changes than Beverly". USA Today gave the film three out of four stars and found that the "strength of the movie lies in these performances and in the situational humor, though ultimately the ending is disappointing, attempting to wrap up loose ends far too neatly".
Entertainment Weekly gave the film a "C+" rating and Lisa Schwarzbaum wrote, "... every scene is bumpered with actorly business and production detail that says more about nostalgia for the pop culture of earlier American decades than about the hard socioeconomic truths of being a poor, young, undereducated parent". In her review for The Washington Post, Rita Kempley criticized Drew Barrymore's performance: "Barrymore, a delightful comic actress, has the spunk for the role, but can't do justice to the complexities of Beverly's conflicted personality. So she comes off as abrasive and neglectful as opposed to headstrong and ambitious, winning no empathy for this sour single mom". Edward Guthmann also had problems with Barrymore's performance in his review for the San Francisco Chronicle: "She never relaxes, never surrenders to the character, but instead tries to justify her and to make us like her despite her selfishness and poor mothering. American actors as a rule are terrified of playing unsympathetic characters, particularly when they've gained the celebrity and box-office appeal that Barrymore has". In his review for the Los Angeles Times, Kenneth Turan criticized the film's direction: "At home with the comedy, even if it is too broad, the director brings next to nothing to the serious scenes; they simply sit there on the screen, empty and forlorn".
The film opened at #2 at the U.S. Box office raking in US$10,404,652 in its opening weekend, behind From Hell.