Drew Barrymore’s ‘Never Been Kissed’ Secrets: Inside The Ultimate 1999 Rom-Com

The late 1990s delivered an absolute golden era for teen cinema. Right alongside the rise of dial-up internet, Y2K panic, and chart-topping boy bands, high school movies dominated multiplexes nationwide. Standing right at the forefront of that pop-culture explosion was *Never Been Kissed*, the hit 1999 romantic comedy that showcased Drew Barrymore at the top of her game. The iconic flick centered on Josie Geller, an ambitious 25-year-old newspaper editor who went undercover as a high school student to break a major story. Along the way, she confronted her traumatizing past as "Josie Grossie" while unexpectedly falling for her English teacher. Decades later, the movie remains an essential staple of nostalgic entertainment. ## Drew Barrymore Never Been Kissed movie details The feature was far more than just another acting gig for Barrymore. It represented a pivotal moment for her career behind the scenes, serving as the first major feature film produced by her banner, Flower Films. Taking control of the project proved she was a powerhouse talent capable of launching massive box-office hits on her own terms. To make the story work, the production assembled a stacked ensemble cast that captured the exact energy of late-'90s Hollywood. Alongside Barrymore, the lineup featured Michael Vartan as the dreamy English teacher, David Arquette as her high school-obsessed brother, plus early-career appearances from Jessica Alba, Leelee Sobieski, and comedy icon Molly Shannon. ## Why Never Been Kissed remains a 1999 rom com classic While 1999 delivered an overwhelming slate of teen hits—including *10 Things I Hate About You*, *She's All That*, and *Varsity Blues*—Barrymore's vehicle stood apart from the pack. It struck a unique balance between extreme awkwardness and heartfelt romance, culminating in one of the most memorable grand-gesture endings in modern movie history on a baseball mound. From fluffy pink prom outfits to instantly quotable lines about love and second chances, the film continues to draw in fresh audiences on streaming services today. It serves as a hilarious, sweet reminder of an unforgettable moment in pop-culture history when high school rom-coms completely ruled the world.