Molly Gunn (Brittany Murphy) is a carefree and fun-spirited girl, living off the ample trust fund of her late rock legend father, Tommy Gunn. Molly falls for singer Neal Fox (Jesse Spencer) when he plays at her birthday party thrown by her best friends, Huey (Donald Faison) and Ingrid (Marley Shelton). They have a night of passion but he leaves in the morning, saying that he can't stay in Molly's carefree life. Adding to Molly's misfortune, she finds out that her father's accountant embezzled her money, so she is left penniless and homeless. She moves in with her best friend, Ingrid who tells her that in order to stay with her, she must find a job.
Molly begins work as a nanny of an eight-year-old hypochondriac and neat freak named Laraine "Ray" Schleine (Dakota Fanning) who is the daughter of Roma Schleine (Heather Locklear), a music executive who is too busy to notice Ray. Ray's father is in a coma and is being treated at home by a private nurse which causes Ray to stifle her emotions to maintain order. Although she enjoys ballet, she refuses to freestyle and often quotes Mikhail Baryshnikov: "Fundamentals are the building blocks of fun." Molly attempts to show her how to have fun, which at first causes much conflict between them, but eventually Ray opens up to let Molly in.
Molly continues to pursue Neal and holds onto his lucky jacket in hopes of seeing him again. After a baking accident, Molly causes a fire that damages Neal's jacket. She redesigns it to fix the damage but Neal breaks up with Molly when he sees it, claiming he has to pursue his music career and does not have time for her flightiness. Soon after, he gets a record deal with Roma and has a hit music video with a song that Molly inspired him to write, all while wearing the jacket Molly made. Disgusted, Molly agrees to Ingrid's suggestions to sell off her possessions so she can prove that she is growing up. However, after a fight, Ingrid kicks Molly out to live with Huey.
The budding friendship between Molly and Ray continues to develop when Molly takes Ray to Coney Island and explains that when her parents died, she ran away to Coney Island and rode the tea cups. She encourages Ray to talk to her comatose father, and promises that it will help him improve. However, Ray's father dies the next day, and Ray tells Roma to fire Molly. In Roma's office, Molly calls Roma out for never paying attention to her daughter. As she leaves, Molly bumps into Neal, who begs to get back together as she was his whole inspiration. Molly turns him down and coldly tells him that he is selfish and only cares about her when she can give him something. Ray runs away from home and Roma begs Molly to find her. Molly finds Ray at Coney Island, riding in the tea cups. At first, Ray tries to be angry with Molly for raising her hopes but then she collapses into Molly's arms, crying, finally coming to terms with her grief.
Molly, deciding to take charge of her own life, takes Ray's advice to auction off her late father's guitar collection to an unknown buyer; this enables her to afford her own place. At the wake for Ray's father, Molly meets other musicians who ask her to design their clothes after seeing Neal's jacket in his video. She and Ingrid also make up and Molly finds Ray to apologize as well. She promises to stay friends with Ray and enrolls in design school after realizing her talent for fashion.
Molly arrives at Ray's recital late and is pleased to see Ray is wearing the tutu Molly designed for her earlier. She is surprised when Ray dances freestyle to Neal singing "Molly Smiles", a song written for her by her father when she was a child. He plays using Tommy Gunn's acoustic guitar, while the remaining ballerinas dance with the other guitars from her father's collection, revealing that he was the anonymous buyer. In a voice over, Ray says that the end was a new beginning for all of them.Brittany Murphy as Molly Gunn
Dakota Fanning as Laraine "Ray" Schleine
Marley Shelton as Ingrid
Donald Faison as Huey
Jesse Spencer as Neal Fox
Austin Pendleton as Mr. McConkey
Heather Locklear as Roma Schleine
Pell James as Julie
Wynter Kullman as Holly
Amy Korb as Kelli
The film opened at number 5 at the US box office, raking in US$11,277,367 in its opening weekend. Uptown Girls was panned by critics, with Rotten Tomatoes giving it a 14% rating based on 111 reviews.
Following Brittany Murphy's death at the age of 32 on December 20, 2009, Dakota Fanning, at age 15, stated that she cherished the time they spent together while working on the film, and that she was "very grateful that [she] had the chance to work with [Murphy]."
Uptown Girls was released on VHS and DVD on 6 January 2004.