Alright, pop that tape in the VCR, maybe hit tracking a couple of times if the picture’s fuzzy – tonight on VHS Heaven, we’re revisiting a gem from the very end of the Clinton era, a movie that practically radiates late-90s charm: 1999’s Never Been Kissed. It landed just as the millennium jitters were setting in, offering a sweet, funny, and profoundly awkward trip back to the horrors and hopes of high school, all spearheaded by the absolutely luminous Drew Barrymore.
This wasn't just another gig for Barrymore; Never Been Kissed was the debut feature from her very own production company, Flower Films. Talk about putting your heart on the line! She stars as Josie Geller, a 25-year-old copy editor at the Chicago Sun-Times who’s smart, capable, but cripplingly insecure, haunted by her nightmare high school experience where she earned the moniker "Josie Grossie." When she gets a chance to go undercover back in high school for a story, it’s pitched as a second chance – a shot at coolness, popularity, and maybe, just maybe, that elusive first real kiss.
### Back to School, Armed with Bad Fashion
Let's be honest, the premise is pure wish-fulfillment, filtered through a comedic lens. Josie’s initial attempts to infiltrate the cool kids' clique are hilariously disastrous. Remember that white feathered monstrosity she wears on her first day? Pure, unadulterated late-90s cringe comedy, and Barrymore sells every awkward moment with a vulnerability that’s instantly endearing. It’s a testament to her performance that even when Josie is being utterly clueless, you’re rooting for her, not laughing at her (well, maybe a little, but affectionately!).
The film smartly contrasts Josie’s memories of her actual teen years (hello, back brace and unfortunate nickname) with her undercover reality. It taps into that universal fear of repeating past mistakes, that feeling that maybe we never really leave high school behind. Director Raja Gosnell, who had previously helmed Home Alone 3 (1997) and would go on to direct the live-action Scooby-Doo (2002), keeps the tone light and breezy, even when dealing with Josie's anxieties. He lets the humor come from the situation and Barrymore's brilliant physical comedy.
### More Than Just Josie Grossie
While Barrymore is the undeniable heart of the film, the supporting cast adds layers of fun. David Arquette, fresh off the Scream franchise (where he met Barrymore), plays her cooler, genuinely popular younger brother Rob Geller, who also enrolls to help his sister navigate the social minefield. Their sibling dynamic feels genuine and provides some of the film's warmest moments. Arquette brings a manic energy that plays perfectly off Barrymore’s earnestness. It's a fun fact that the high school they filmed at, John Burroughs High School in Burbank, California, has a serious screen pedigree – it was also the main setting for the classic TV show The Wonder Years! Feels appropriate, right?
And then there's the dreamy English teacher, Sam Coulson, played by Michael Vartan in a role that definitely launched a thousand crushes just before he hit it big with TV's Alias (2001-2006). The ethical quandary of their potential romance (she's posing as 17, he thinks she's a student) adds a necessary bit of tension, even if we all know where it's heading. Their chemistry is sweet, built on shared literary interests and shy glances across the classroom. Plus, keep your eyes peeled for early appearances by Jessica Alba as one of the mean girls and a blink-and-you'll-miss-it role for James Franco! Even John C. Reilly and Molly Shannon pop up in memorable smaller parts, adding comedic weight.
### Capturing the End of an Era
Watching Never Been Kissed now feels like opening a time capsule. It’s pre-social media, pre-smartphones; the high school dynamics, while heightened for comedy, feel refreshingly grounded compared to some of today's slicker teen fare. The problems are relatable – fitting in, finding your voice, dealing with bullies (led impeccably by Leelee Sobieski), navigating first crushes. The soundtrack, packed with bands like The Smiths, Jimmy Eat World, and Semisonic, instantly transports you back. Remember popping this tape in on a Friday night, maybe after grabbing it from Blockbuster? It just felt like the kind of movie made for sleepovers and hopeful sighs.
The script, penned by Abby Kohn and Marc Silverstein (who would later write He's Just Not That Into You), balances the laughs with genuine heart. Josie’s journey isn’t just about becoming popular; it’s about self-acceptance. It took a respectable $84.5 million at the box office against its $25 million budget – not a world-beater, but a solid hit that cemented its place as a go-to comfort watch for a generation. Critics were somewhat mixed at the time, but audiences embraced its charm, and it's arguably held up better than some of its contemporaries precisely because of its earnestness.
### The Final Cut
Never Been Kissed isn't trying to be edgy or subversive. It's a sweet, funny, and ultimately optimistic film about second chances and finding the courage to be yourself, even if yourself was once "Josie Grossie." Drew Barrymore is utterly captivating, carrying the film with effortless charm and relatable awkwardness. It perfectly captures that specific late-90s moment where teen comedies could still be genuinely heartfelt without a thick layer of irony.
Rating: 8/10
The score reflects its strong performances, genuinely funny moments, relatable themes, and its status as a top-tier feel-good movie from the era. It might not be complex, but it achieves exactly what it sets out to do with warmth and style. It’s a reminder that sometimes, the most awkward journeys lead to the sweetest destinations – a perfect slice of late-VHS-era comfort food.