Drew Barrymore (who also produced the rom-com), Michael Vartan and Leelee Sobieski knocked it out of the park with Never Been Kissed. Relive the magic of the 1999 charmer, now streaming on Fandango.
Along with Napster, Harry Potter and Y2K panic, teen rom-coms were all the rage in 1999.
It's unclear if a certain sect of screenwriters got together and agreed that the waning years of the millennium were the time to churn out delightful fare for the underage set, but between 10 Things I Hate About You, Varsity Blues, Cruel Intentions and She's All That it was quite the time to be in high school and dreaming wistfully of first loves and perfect prom dates.
Albeit somewhat disturbing to realize that a bespectacled Rachael Leigh Cook and a poorly attired Drew Barrymore are what pass for impossibly nerdy in Hollywood.
Such was the premise for Never Been Kissed, streaming free now, on Fandango. Barrymore's Josie Geller is the youngest editor at the Chicago Sun-Times with a penchant for correcting her colleagues' grammar, but not the skills necessary to land the reporting job of her dreams.
Given a shot to prove herself, she takes an assignment going undercover at nearby South Glen South high school.
The only issue? Josie didn't exactly have the strongest social game as a teen the first time around. And while she totally has been kissed, she's the type of hopeless romantic that believes she should only be puckering up for "the person you're supposed to kiss for the rest of your life."
Basically, she's totally going to kill it with her fellow youths.
Dressed in an unfortunate all-white ensemble, Josie quickly befriends brainy Aldys (Leelee Sobieski), an aspiring professor, novelist and flautist who's already figured out that her best years lie ahead, and develops a troubling crush on Cool Teacher Sam Coulson (Michael Vartan).
But with prom fast approaching, hanging with the math club (appropriately named the Denominators) and lusting over an English instructor with boundary issues is not going to get Josie the cover story she's after.
For that she relies on brother Rob (David Arquette), also going undercover, to gain her entrée into the cool kids group, which includes a pre-stardom James Franco and Jessica Alba.
With Rob vouching for her—perhaps the truest line uttered in the movie is when he tells Josie, "All you need is for one person to think you're cool, and you're in. Everyone else will be scared to question it"—she scores a popular date to the big dance, the title of queen and the chance to finally yell out, "I'm not Josie Grossie anymore!"
We're not saying the movie is without its troubling moments.
The so-called dream guy, whose name is actually Guy (Jeremy Jordan), refers to unpopular girls as "dogs," and the school clearly has very lax admission standards. But the overarching message about how it's cool to be yourself is sweet. And the whole teacher-falling-for-a-student storyline is made more palatable by the winning charms of Michael Vartan.
By the end, after Josie has apologized for duping him and asked for a shot at a legitimate relationship with all the trappings of a rom-com, who wasn't rooting for Mr. Coulson to show up at the packed baseball stadium and just kiss her already?
