Never Been Kissed (released in theaters on April 9, 1999) follows Josie Geller (Drew Barrymore), a bright but socially awkward 25-year-old copy editor at the Chicago Sun-Times who feels stuck in a perpetual state of teenage rejection. Her life takes a dramatic turn when her editor assigns her to go undercover as a high school student to report on the secret lives of modern teens.
Desperate to prove her journalistic worth, Josie returns to the classroom, only to find herself reliving the “Josie Grossie” traumas of her past.
However, with the help of her charismatic brother Rob (David Arquette), who poses as a student to help her gain popularity, she manages to infiltrate the cool crowd.
Along the way, she develops feelings for her sensitive English teacher, Sam Coulson (Michael Vartan), creating a high-stakes conflict between her professional duty, her blossoming romantic feelings, and the inevitable reveal of her true identity during a climactic baseball game.
Barrymore radiates warmth and vulnerability as Josie, anchoring the film with a performance that makes her journey from outcast to confident woman deeply resonant.
The film is packed with notable supporting talent, including a young Jessica Alba, Leelee Sobieski, and Jordan Ladd as the high school hierarchy, alongside veteran comedic turns from Molly Shannon, John C. Reilly, and Garry Marshall.
Cress Williams and Jeremy Jordan contribute to the vibrant Chicago setting.
Marley Shelton, Octavia Spencer and James Franco round out the supporting cast.
Drew Barrymore in Never Been Kissed (Photo/20th Century Fox)
Reception for Never Been Kissed
Never Been Kissed grossed $11.8 million on its opening weekend, finishing second at the box office behind The Matrix ($22.6 million) on its second weekend.
The film would gross $84.6 million worldwide.
Roger Ebert gave Never Been Kissed three out of four stars in his review.
Legacy
Never Been Kissed‘s legacy is defined by its enduring status as a cornerstone of the late-nineties romantic comedy revival.
It successfully subverted the “ugly duckling” trope by focusing on internal growth and the importance of being true to oneself rather than simply undergoing a physical makeover.
The movie is responsible for one of the most iconic romantic gestures of the era—the countdown on the pitcher’s mound—which has been referenced and parodied in countless media since.
Beyond the romance, it remains a nostalgic touchstone for its fashion, its soundtrack, and its empathetic look at the hierarchy of American high schools.
Never Been Kissed solidified Barrymore’s transition into a powerhouse producer and leading lady who could blend slapstick humor with genuine sentiment, ensuring the film’s place as a perennial favorite for anyone who ever felt like they didn’t quite fit in.
