Never Been Kissed

1999 was, by almost any metric, the greatest year in the history of cinema. We got The Matrix, Fight Club, and Magnolia. But amidst those heavy-hitting, world-altering masterpieces, there was a specific, bubblegum-scented pocket of the box office dedicated to the "teen reinvention" comedy. While everyone else was questioning the nature of reality, Drew Barrymore was just trying to survive a prom. I recently revisited Never Been Kissed on a whim while eating a bowl of cereal that had gone slightly soggy because I spent twenty minutes trying to remember where I’d seen the guy playing the teacher before. It turns out, this movie is the ultimate 1990s time capsule—charming, deeply earnest, and more than a little problematic when you squint at it through a modern lens.

The "Josie Grossie" Trauma

The film follows Josie Geller (Drew Barrymore), a twenty-five-year-old copywriter at the Chicago Sun-Times who is desperate to be a "real" reporter. When her editor—played with wonderful, grumpy energy by John C. Reilly (long before his Step Brothers antics)—sends her undercover at a local high school to find out "what the kids are into," Josie has to face her greatest demon: her own teenage history.

Josie was the girl who wore a metallic prom dress with white feathers and got pelted with eggs. Drew Barrymore is the only person on the planet who could make this role work. She has this innate, radiating kindness that prevents the character from becoming a caricature of a "nerd." She’s clumsy, she’s socially terrified, and she’s genuinely brilliant. Looking back, her performance is a masterclass in vulnerability—she makes you feel every ounce of that "Josie Grossie" shame. It’s the kind of role that reminds me why she was the queen of the rom-com era; she never feels like she’s punching down at the character.

A Cast of "Before They Were Famous"

One of the best parts of watching these late-90s relics is the "hey, it's that person!" game. You’ve got a young Jessica Alba as the resident mean girl, Kirsten, long before she was a blockbuster star or a lifestyle mogul. Then there’s Molly Shannon, fresh off her Saturday Night Live peak, playing Josie’s colleague with the kind of chaotic energy that suggests she might burst into a "Superstar!" pose at any second.

But the real MVP of the supporting cast is David Arquette as Josie’s brother, Rob. Rob was the cool kid who peaked in high school and is now working at a tiki bar, but he goes back undercover with Josie to help her fit in. Arquette’s performance is basically a concentrated dose of 1999 chaos. Whether he’s wearing a Hawaiian shirt or teaching Josie how to "be cool," he brings a weird, lived-in sweetness to the sibling dynamic. He’s the one who understands that high school isn't about grades; it's about the performance of confidence.

The Teacher-Student Elephant in the Room

Here is where the retrospection gets a bit sticky. The central romance involves Josie falling for her English teacher, Sam Coulson, played by Michael Vartan. Now, Sam is a "dreamy" teacher in the late-90s sense—he likes literature, he looks great in a sweater, and he actually listens to his students. But, even though we as the audience know Josie is twenty-five, he thinks she’s seventeen for 90% of the movie.

The central romance in this movie is essentially a slow-motion car crash of professional ethics. I found myself shouting at the screen, "Sam, you are a mandatory reporter! Stop flirting with the 'student' at the diner!" It’s a trope that was ubiquitous in the Dawson's Creek era, but today it feels incredibly cringey. The film tries to bypass the creepiness by making Sam "noble" and having him wait for her to turn eighteen (or so he thinks), but it’s a tough sell in the 2020s. Yet, Michael Vartan is so charmingly bewildered that you almost—almost—forgive the script for its questionable moral compass.

A Farewell to the Analog Newsroom

What struck me most on this rewatch wasn't the romance, but the setting. The Chicago Sun-Times office in this movie is a prehistoric wonderland. It’s filled with clunky beige monitors, sprawling desks covered in actual paper, and landline phones with those incredibly long, tangled cords. There’s something deeply nostalgic about the way the film portrays the "big break" in journalism—waiting for the physical newspaper to hit the stands to see if your story made the front page.

Director Raja Gosnell, who would go on to direct the live-action Scooby-Doo movies, keeps the pace breezy and the colors saturated. It has that bright, optimistic "pre-Y2K" glow where every problem can be solved by a grand gesture and a well-timed slow-motion walk down a hallway. Even if the logic of the undercover assignment makes zero sense—why would a major newspaper spend thousands of dollars to send a woman back to high school to find out that teenagers like... being popular?—it doesn't really matter. The film captures the feeling of wanting a do-over, a chance to be the person you wish you were when you were seventeen.

Never Been Kissed isn't a perfect film, and its central romantic conceit has aged like milk left out in a locker over summer break. However, it remains a testament to the sheer, unadulterated star power of Drew Barrymore. It’s a movie that celebrates the losers and the late bloomers, wrapped in a soundtrack of 90s alternative pop that still hits all the right notes. If you can ignore the HR nightmare of the Sam/Josie relationship, it’s a cozy, nostalgic hug of a movie that reminds us that some things—like the fear of being rejected at prom—are truly universal.