Honestly, it’s hard to believe it’s been over twenty-five years since Josie Geller first stepped onto the screen in her white marabou-trimmed suit. You know the one. That cringe-inducing, heart-shattering moment where she realizes her prom "date" was just a cruel prank. It’s the scene that defines the movie. But when we look back at the Never Been Kissed cast, it’s not just about Drew Barrymore’s endearing awkwardness. It’s about a weirdly perfect alchemy of future superstars, indie darlings, and character actors who somehow made a goofy rom-com about a reporter going undercover in high school feel like a core memory.
The late nineties were a strange time for teen cinema. We had Scream, Cruel Intentions, and 10 Things I Hate About You. Then there was Never Been Kissed. It was softer, weirder, and featured a protagonist who was actually an adult pretending to be seventeen. That’s a risky premise. In the wrong hands, it’s creepy. In the hands of this specific ensemble, it’s a time capsule of post-grunge optimism.
Drew Barrymore and the Power of Josie "Gross" Geller
Drew Barrymore wasn't just the lead; she was the engine. This was the first film produced by her company, Flower Films. If you watch closely, you can see how much of her own vulnerability she poured into Josie Geller. Barrymore has this uncanny ability to be both a movie star and the girl you want to protect from the "popular" kids.
Josie Geller is a copy editor at the Chicago Sun-Times. She’s brilliant, neurotic, and desperately lonely. When she’s tasked by her boss, Rigfort (played with a delightful, crusty cynicism by Garry Marshall), to go undercover at South Beach High, the stakes are absurdly high for her career and her ego. Barrymore plays the physical comedy to the hilt—the "pajama party" mishap, the accidental ingestion of certain substances at a party—but she grounds it in a very real desire to be seen. It's why we root for her.
Michael Vartan and the "Problematic" Teacher Crush
Let’s talk about Sam Coulson. Michael Vartan, with his floppy hair and "I read literature in my spare time" energy, was the ultimate nineties sensitive guy. He was the English teacher who actually cared about his students' thoughts on Shakespeare. Of course, the central conflict of the film is that he falls for Josie, thinking she’s a student.
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In 2026, we look at this through a different lens. It’s a bit messy, right? A teacher falling for someone he believes is his minor student is a massive red flag. However, within the logic of 1999 romantic comedies, Vartan plays Sam with such genuine intellectual loneliness that you almost forget the ethical catastrophe unfolding on screen. He wasn't trying to be a predator; he was just a guy who finally found someone who understood his references. Vartan’s chemistry with Barrymore is what saves the movie from being an episode of a true-crime podcast.
The Secret Weapon: David Arquette as Rob Geller
If Barrymore is the heart of the Never Been Kissed cast, David Arquette is the soul. He plays Rob, Josie’s brother, a former high school superstar who peaked in the eleventh grade and is now working at a tiki bar. Arquette is often dismissed as just a "wacky" actor, but his performance here is surprisingly nuanced.
When Rob decides to go back to high school to help Josie fit in, he becomes the "cool kid" all over again. The scene where he eats a mountain of coleslaw to win over the jocks is legendary. But it’s the quiet moments—where he tells Josie she’s always been cool to him—that actually land. Arquette captures that specific type of sibling bond where one person is the protector and the other is the pioneer. He brought a frantic, lovable energy that balanced out the slower, romantic beats of the film.
The Supporting Players: A Who's Who of Nineties Talent
Look at the hallways of South Beach High in this movie. It’s a goldmine. You’ve got the "Three G’s"—the popular girls who rule the school with an iron fist and very expensive headbands.
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- Marley Shelton played Kristin, the leader. She was the quintessential "mean girl" before Regina George took the throne.
- Jessica Alba was Kirsten. This was one of her first major roles before Dark Angel turned her into a global icon. Seeing a young Alba play a snarky, high school bully is a trip.
- Jordan Ladd rounded them out as Gibby.
Then you have the nerds. Leelee Sobieski played Aldys, the leader of "The Denominators." Sobieski was everywhere in the late nineties, from Deep Impact to Eyes Wide Shut. Here, she provides the moral compass. She represents the person Josie should have been in high school—someone comfortable in her own skin, even if that skin is covered in a math club vest.
And we can't forget the newsroom. John C. Reilly as Augustus "Gus" Leich, Josie's immediate supervisor, is a masterclass in understated comedy. Reilly hadn't yet fully leaned into the Will Ferrell-style comedies that would define his later career, so he plays Gus with a dry, weary competence that feels incredibly real to anyone who has ever worked in a frantic office environment. Molly Shannon also pops up as Anita, providing the necessary "horny best friend" energy that every nineties rom-com required by law.
Why the Ensemble Worked Where Others Failed
Most teen movies of this era relied on a single star. Never Been Kissed worked because it felt like a community. The contrast between the jaded world of the newspaper office and the high-stakes, neon-colored world of high school creates a dual narrative that keeps the pacing tight.
Director Raja Gosnell (who also did Home Alone 3 and later Scooby-Doo) leaned into the artifice. The costumes were loud. The sets were bright. It felt like a fever dream of what high school is supposed to be, which makes sense because we are seeing it through the eyes of a woman who is reliving her trauma.
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The Never Been Kissed cast also benefited from the era's casting philosophy: find character actors and let them cook. Gary Marshall, a legendary director in his own right, being in the film as a supporting actor adds a layer of meta-authority. It’s like the movie is being blessed by the creator of Pretty Woman.
The Legacy of the "Big Kiss" Scene
The climax of the film—Josie standing on the pitcher's mound, waiting for a guy who thinks she’s a liar to come and kiss her in front of the entire town—is objectively insane. It shouldn't work. It’s too sentimental. It’s too public.
But the reason it works is the buildup provided by the cast. We’ve seen Josie’s growth. We’ve seen Rob’s redemption. We’ve seen Sam’s inner turmoil. By the time the clock is ticking down and The Beach Boys' "Don't Worry Baby" starts playing, you are fully invested. When Vartan finally walks out from the dugout, it’s a release of tension that has been building for ninety minutes.
Practical Takeaways for Fans of the Film
If you're revisiting the movie today, there are a few things to keep in mind to truly appreciate what this cast pulled off:
- Look for the cameos. James Franco has a tiny, uncredited role as one of the popular kids. It’s a "blink and you’ll miss it" moment that shows how much talent was flowing through Hollywood at the time.
- Appreciate the "Denominators" subculture. The film was ahead of its time in showing that the "nerds" were actually the ones having the most fun. Aldys and her friends are the only ones who seem to have genuine hobbies and interests outside of social standing.
- Note the soundtrack integration. The music is a character in itself. From the Cardigans to R.E.M., the songs aren't just background noise; they are emotional cues that the cast reacts to.
The film serves as a reminder that "coolness" is a moving target. The things that made Josie a pariah in the eighties (being smart, being earnest, being "gross") are the things that make her a hero in the nineties. The cast navigated this shift perfectly, showing that the only thing more painful than being a teenager is having to be one twice.
To get the most out of your next rewatch, pay attention to the background actors in the prom scene. The sheer amount of period-accurate "formal wear" is a fashion study in itself. You might also want to look up the filming locations in Chicago; many of the exteriors for the Sun-Times and the high school still look remarkably similar today. Whether you're a fan of Drew Barrymore's career or just a sucker for a good "underdog wins" story, this ensemble remains one of the most cohesive and charming examples of the genre.