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Drew Barrymore’s Beloved Nerd Girl Classic Never Been Kissed Turns 20

"I'm not Josie Grossie anymore!"

In yet another installment of “oh no, how did we get so old?!”, this week marks the 20th anniversary of the Drew Barrymore romcom classic Never Been Kissed. The 1999 film, directed by Raja Gosnell, stars Barrymore as Josie Geller, a meek copy editor for the Chicago Sun-Times who dreams of being a reporter. Her big break comes when the paper’s editor Rigfort (played hilariously by Garry Marshall) assigns her to go undercover as a student at a local high school.

The only problem is, Josie was a massive nerd in high school, and has zero idea how to get in with the cool kids. What follows is a Cinderella story in which Josie stumbles her way into popularity and develops feelings for her handsome English teacher Mr. Coulson (Michael Vartan).

Re-watching the film felt like reuniting with an old high school friend. The movie was massively popular for my generation, quickly becoming an eminently quotable slumber party staple. It was especially poignant if you were a nerdy girl, thanks to Barrymore’s vanity-free performance.

High school Josie was not like the other nerd girls of popular culture at the time. She wasn’t a hot girl in glasses and a ponytail; she was a hot mess. Barrymore delights in playing the awkward and insecure Josie, as well as the mousy adult version of her pre-makeover. Josie’s nerdiness, while played for laughs, never punches down. We genuinely feel for her when her high school crush rejects her as part of a cruel prank.

Even more satisfying, we see Josie thrive when she finds her tribe, led by nerd queen Aldys (Leelee Sobieski—who, to be fair, is a hot girl in glasses and a ponytail). Josie joins the mathlete team The Denominators, and we see her having a blast at competitions and roasting marshmallows over Bunsen burners.

In one highly relatable scene, Josie and Aldys spend the night drinking milkshakes and driving around town while loudly belting out “Free to Be You and Me.” Before Never Been Kissed, nerdy girls were hard-pressed to find images of themselves that were not mocking or degrading.

Never Been Kissed also features a strong supporting cast, like Molly Shannon as Josie’s horny co-worker Anita, who accidentally gets roped into teaching Sex Ed. There’s John C. Reilly as Josie’s curmudgeonly boss Gus, as well as several actors in the ensemble who went on to become famous, from Octavia Spencer to James Franco to Jessica Alba. The film serves as a terrific time capsule of late 90s fashions, thanks to Mona May’s vibrant costuming (May also did the costumes for Romy and Michele’s High School Reunion and Clueless, making her the architect of countless 90s fashion trends).

But the best supporting performance by far is David Arquette as Rob, Josie’s goofy jock brother who joins her at high school and helps her become popular. Arquette has never been better, bringing genuine emotion to what could have essentially remained a one-joke character.

Twenty years later, the film holds up surprisingly well. While modern audiences may be squicked out by Josie flirting with Vartan’s hunky English teacher (who thinks she’s a teen), that storyline remains chaste enough to not feel so gross.

Never Been Kissed remains one of the best teen movies and romcoms of the ’90s, and a true ode to nerdy, overly enthusiastic girls of all ages. If you’re in the mood for a rewatch, the film is currently available to stream on HBO NOW.

(via CNN, image: 20th Century Fox)

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Chelsea was born and raised in New Orleans, which explains her affinity for cheesy grits and Britney Spears. An pop culture journalist since 2012, her work has appeared on Autostraddle, AfterEllen, and more. Her beats include queer popular culture, film, television, republican clownery, and the unwavering belief that 'The Long Kiss Goodnight' is the greatest movie ever made. She currently resides in sunny Los Angeles, with her husband, 2 sons, and one poorly behaved rescue dog. She is a former roller derby girl and a black belt in Judo, so she is not to be trifled with. She loves the word “Jewess” and wishes more people used it to describe her.