Okay, let's rewind the tape just past the 90s threshold, right into the dawn of the new millennium, where the teen comedy genre was still riding high on a wave of hormones, heartbreak, and hilariously mismatched couples. Floating somewhere in that sea of Y2K high school flicks is 2000’s Whatever It Takes, a film that might not have etched itself into the Hall of Fame alongside Clueless or 10 Things I Hate About You, but feels undeniably like a product of its time – a warm, fuzzy, slightly awkward cinematic yearbook photo. It arrived just as the VHS tape was taking its final bow, making it a perfect candidate for a fond look back here at VHS Heaven.
The Old Switcheroo, Y2K Style
At its heart, Whatever It Takes is yet another spin on the timeless tale of Cyrano de Bergerac, transplanting Edmond Rostand's 17th-century poetic woes into the brightly lit hallways of a turn-of-the-millennium American high school. Directed by David Raynr and penned by Mark Schwahn (who would later strike gold creating the long-running teen drama One Tree Hill), the setup is comfortingly familiar. We have Ryan Woodman (Shane West), our sensitive, slightly geeky protagonist, hopelessly crushing on the most popular girl in school, Ashley Grant (Jodi Lyn O'Keefe). Meanwhile, Ryan's confident, perhaps slightly dim-witted jock cousin, Chris (James Franco in a very early role), has his eyes set on Ryan's intelligent, down-to-earth best friend and neighbor, Maggie Carter (Marla Sokoloff).
Naturally, neither guy feels equipped to woo their respective dream girl. So, they hatch a plan: Ryan will coach Chris on how to win over the bookish Maggie (feeding him lines, suggesting thoughtful gestures), while Chris will use his BMOC status to help Ryan get noticed by the seemingly unattainable Ashley. What could possibly go wrong? Well, if you’ve ever seen a movie before, you probably have a good idea. It's a premise built on deception, awkward encounters, and the slow-dawning realization that maybe, just maybe, they’re chasing the wrong people.
A Cast of Familiar Faces (Before They Were Faces)
Part of the fun in revisiting Whatever It Takes now lies in its cast, a snapshot of young actors on the cusp of greater recognition. Shane West, fresh off teen dramas like Once and Again, brings a likable earnestness to Ryan. You genuinely feel for his predicament, even when his choices are questionable. Marla Sokoloff, who many would recognize from The Practice or as Gia Mahan in Full House and Fuller House, is arguably the film's heart. She imbues Maggie with a warmth and intelligence that makes you root for her happiness from the start. Jodi Lyn O'Keefe, already known for playing tough girls and mean girls in films like She's All That (1999), leans into the popular archetype well, though the script doesn't give her as much depth as Sokoloff's character.
And then there's James Franco. Seeing him here, pre-Spider-Man, pre-everything, as the slightly goofy, well-meaning jock Chris is a trip. It’s not a complex role, but he handles the comedic aspects with an energy that hints at the varied career to come. Keep your eyes peeled too for blink-and-you'll-miss-them appearances from Aaron Paul (yes, Breaking Bad's Jesse Pinkman!) as one of Ryan’s dorky friends, and Colin Hanks as another classmate. It’s like a high school reunion of future stars.
Peak Millennium Teen Vibes
This movie feels like 2000. The fashion (questionable hair choices, baggy pants, spaghetti straps), the technology (bulky computer monitors, the nascent internet playing a minor role), and especially the soundtrack – packed with the pop-punk and alternative rock that dominated the airwaves back then (think Lit, Blink-182, Tal Bachman's "She's So High"). It captures that specific end-of-an-era optimism before the world shifted later that decade. For anyone who navigated high school around this time, watching Whatever It Takes is like opening a time capsule, complete with awkwardly choreographed dance scenes and the ubiquitous prom-night climax.
While Mark Schwahn's script hits all the expected beats of a teen rom-com, it does so with a certain sincerity. The dialogue might not sparkle like Diablo Cody's work, but it captures the earnest melodrama of teenage crushes. It doesn't reinvent the wheel, nor does it try to. Its ambition seems squarely focused on being a sweet, entertaining ride through familiar territory. Filmed primarily around Southern California high schools, it has that sunny, slightly generic look common to many teen films of the period.
Retro Fun Facts: By the Numbers
Whatever It Takes wasn't exactly a box office juggernaut. Made on a reported budget of around $9 million, it pulled in roughly the same amount domestically during its theatrical run. This essentially meant it broke even before marketing costs, marking it as more of a minor blip than a major hit in a crowded teen market. Critical reception at the time was also rather chilly (it currently sits at a frosty 16% on Rotten Tomatoes). Yet, like many films from the era, it likely found a second life on home video and cable, becoming a nostalgic favorite for a specific audience who caught it on a Friday night rental run. The Cyrano plot device, while classic, felt perhaps a little well-trodden even then, but the earnestness of the cast helps sell it.
Still Worth the Rental Fee?
Look, Whatever It Takes isn't high art. It's predictable, packed with tropes, and occasionally dips into cheesy territory. But revisiting it isn't about discovering a lost masterpiece. It's about reconnecting with a feeling – that specific blend of awkwardness, hope, and oversized emotions that defined so many turn-of-the-millennium teen movies. The cast is charming, particularly the core four, and there's a genuine sweetness beneath the formula. It doesn't quite reach the heights of its genre predecessors, lacking the sharp wit of Clueless or the iconic moments of 10 Things I Hate About You, but it delivers exactly what it promises: a light, breezy, and nostalgic high school romance.
Rating: 6/10
This rating reflects the film's status as a perfectly serviceable, if unremarkable, entry in the Y2K teen canon. It earns points for its likable cast (especially Sokoloff and the pre-fame Franco/Paul/Hanks sightings), its earnest execution of the Cyrano premise, and its potent dose of era-specific nostalgia. It loses points for its predictability and lack of truly memorable standout moments or sharp writing. It's enjoyable comfort food cinema, a pleasant way to spend 90 minutes reminiscing about a simpler time in teen movies.
It’s the kind of movie you’d grab off the “New Releases” wall at Blockbuster, watch with friends, and mostly forget by Monday, but rediscovering it now brings a warm smile – a reminder of when high school problems felt like the whole world, and finding the right words (even borrowed ones) felt like the most important mission ever.