Jessie Montgomery Ally Sheedy is a bratty, hard-partying rich girl in her mid-20s. Her self-indulgent lifestyle, marked by a blatant disregard for rules and for others—including herself—has worn thin on her father, Charles Montgomery Tom Skerritt, a widowed philanthropist who has often spoiled her. When Jessie’s boyfriend Brent Jason Beghe ends things, fed up with her immaturity and lack of values, she barely blinks an eye and moves on. Then a string of events accelerates: Brent’s breakup becomes a flashpoint, and Jessie’s world explodes when she is arrested for drug possession and DWI with a suspended license, even attempting to bribe the arresting officers. Charles blames himself for what his daughter has become, lamenting the years when he spoiled her and left her in the care of his staff, rather than laying down the law.
Outside, a shooting star streaks across the sky, and with it comes a magical twist: Jessie’s identity is erased, leaving her fully clothed but stripped of resources, friends, and family. Stella Winston Beverly D'Angelo, a fairy godmother who has been assigned to the Montgomery family, swoops in to explain the bizarre fate that has befallen Jessie as a consequence of Charles’s wish. Jessie, true to her skeptical streak, doesn’t believe Stella’s story at first, and when she returns to the family mansion, neither Charles nor the staff recognize her; even Jimmy the dog looks right through her. After a failed attempt to crash the gates of the mansion, Jessie is forced to flee as the police arrive.
Roaming the streets, Jessie stumbles into a group of party friends who insist they have never seen her before. A renewed encounter with Stella follows, and the fairy godmother lays out a path for Jessie: she must learn to work and support herself. Jessie, who has never held a job—having dropped out of junior college after “six years”—takes a bold step and lands a job as a live-in maid for an eccentric Malibu family: Stan Starkey Dick Shawn, his wife Georgette Valerie Perrine, and their daughter Brie Rain Phoenix. The Starkeys are a peculiar mix of charm and chaos; years earlier they had won millions in a lottery and now chase a dream of breaking into the music business as talent agents.
As Jessie settles into her new role, she forms bonds with the Starkeys’ other staff members. She befriends Audrey Merry Clayton, the cook and a once-promising singer, and Maria Begonya Plaza, another live-in helper. The chauffeur Nick McGuire Michael Ontkean proves to be an ally and potential love interest, a writer who also longs to make it in music. Through these relationships, Jessie discovers the value of loyalty, friendship, and hard work, internalizing a new sense of self-respect that had long eluded her.
As Jessie helps Nick and Audrey navigate the murky waters of the music industry—an arena that promises both opportunity and exploitation—her outlook shifts from entitlement to effort and cooperation. She begins to experience genuine companionship and mutual support, developing meaningful connections with the people around her. In the process, Jessie’s old life—her father’s money, her social circles, and the comfort of an effortless existence—starts to fade away, replaced by a sense of purpose and belonging she never knew she craved.
The story culminates as Nick and Audrey finally gain traction in their musical ventures, and Jessie’s transformation becomes undeniable. Her father and the other familiar faces from her former life begin to recognize the change in her, signaling a reconciliation of sorts. Yet this recognition does not erase the new path she has chosen. Jessie continues her relationship with Nick, and the film closes with the implication that they may marry and build a life rooted in love, respect, and shared ambition rather than wealth and status alone. The ending suggests a hopeful future where Jessie has grown from a self-centered youth into a capable partner who values integrity and connection as much as success.
