Drive Me Crazy, the 1999 teen romantic comedy, stands out in its crowded genre by mixing sharp wit, likeable leads, and warmhearted coming-of-age themes. Anchored by Melissa Joan Hart and Adrian Grenier (Entourage), the film turns a familiar premise—teens faking romance for ulterior motives—into a breezy, relatable exploration of social divides and genuine connection.
Nicole Maris (Hart) and Chase Hammond (Grenier) are next-door neighbors and former childhood best friends who’ve drifted into opposing social cliques by their senior year.
Nicole is part of the in-crowd, busily organizing the school’s centennial dance and hoping to attend it with basketball star Brad. When Brad invites someone else, Nicole is left scrambling for an alternative date.
Meanwhile, Chase has just been dumped by his activist girlfriend, Dulcie (Ali Larter).
Both reeling from rejection, Nicole and Chase hatch a plan to pose as a couple to make their exes jealous and regain their social footing.
As Nicole gives Chase a makeover to fit her crowd, they begin to infiltrate each other’s friend groups and private worlds.
The ruse takes unexpected turns as real feelings emerge amid misunderstandings, including a pivotal party where Nicole witnesses Chase with her best friend Alicia, unraveling their partnership.
Amid reconciliations and the school dance, Nicole and Chase realize that their scheme has brought them closer to what they really wanted all along.
The film ends with tender moments, not just between the teens, but their single parents as well, hinting at new beginnings for both families.
Adrian Grenier in Drive Me Crazy (Photo/20th Century Fox)
Cast and Chemistry
Beyond Hart and Grenier’s charming performances, Drive Me Crazy features supporting turns from Stephen Collins, Faye Grant, Keri Lynn Pratt, Kris Park, Mark Webber, Gabriel Carpenter, Jordan Bridges and Mark Metcalf.
The cast’s collective chemistry and comedic timing bolster a script that respects its high school audience’s intelligence and emotional reality.
Reception for Drive Me Crazy
Drive Me Crazy grossed $6.8 million on its opening weekend, finishing sixth at the box office.
The film would gross $22.6 million in its theatrical run.
Legacy
Drive Me Crazy became a staple of late-90s teen culture, buoyed by soundtrack hits including (You Drive Me) Crazy by Britney Spears and repeated cable airings.
Its enduring appeal lies in portraying high school life with smarts and heart—sidestepping the shallow tropes that often bog down the genre.
For many in its audience, it remains a nostalgic touchstone, remembered for its blend of humor, real emotion, and the possibility of change and acceptance at any age.
