Little Sister (released on Sept. 17, 1992) is a spirited entry in the long-standing tradition of cinematic cross-dressing comedies. The film captures the lighthearted, often absurd energy of early-nineties campus life, blending the rowdy tropes of the fraternity movie with a surprisingly sweet romantic core.
It is a film that thrives on the comedic timing of its youthful lead and the charm of its ensemble, offering a nostalgic look at the lengths to which a smitten heart will go to secure a second chance. While it operates within the framework of a broad farce, it maintains a gentle sincerity that distinguishes it from the more cynical teen comedies of the era.
Bobby (Jonathan Silverman) is a college student who finds himself hopelessly infatuated with Diana (Alyssa Milano), a beautiful and intelligent girl he met briefly at a party.
After a disastrous initial impression, Bobby realizes that the only way to get close to her is to infiltrate her world.
When he discovers that Diana’s sorority is looking for new “little sisters,” Bobby concocts a desperate and elaborate plan: with the help of his skeptical best friend Mike (George Newbern), he undergoes a total transformation to become “Roberta.”
Navigating the treacherous social waters of the sorority house, Roberta manages to get pledged, leading to a series of high-stakes comedic set-pieces as Bobby tries to maintain his feminine disguise while living in close quarters with his crush.
The situation is further complicated by the presence of Catherine (Leilani Sarelle), the sorority’s intense leader, and Adrienne (Tia Carrere), who adds another layer of competition and campus intrigue.
As Roberta, Bobby becomes Diana’s confidante, learning her true thoughts and feelings in a way he never could as himself.
However, the double life becomes increasingly difficult to manage as he falls deeper in love and begins to feel the guilt of his deception.
The narrative builds to a chaotic climax during a major campus event where Bobby’s secret is threatened with exposure, forcing him to choose between the safety of his disguise and the risk of revealing his true identity to win Diana’s heart for real.
Alyssa Milano and Jonathan Silverman in Little Sister (Photo/LIVE Home Video)
Legacy of Little Sister
Little Sister is defined by its status as a quintessential “guilty pleasure” of the early 1990s, frequently remembered for Silverman’s energetic performance in a dual role.
It is often cited as a key moment in Milano’s transition from child star to leading lady, showcasing the effortless charisma that would define her later career.
The film is celebrated for its bright, vibrant aesthetic and a soundtrack that perfectly encapsulates the pop-culture transition from the eighties into the nineties.
Little Sister is also noted for featuring early roles for Carrere and Newbern.
Release Information
Little Sister was released directly to video by Live Home Video.
