Alright, fellow tape travelers, let’s dig deep into the dusty corners of the video store memory palace for a title that sounds epic but delivers something... else entirely. Remember stumbling across that bold cover for Trojan War (1997) in the comedy section, maybe nestled between Can’t Hardly Wait and American Pie? The name promised swords and sandals, maybe even a giant wooden horse. What we got instead was pure, unadulterated, late-90s high school franticness, centered around arguably the least epic quest imaginable: a desperate, night-long search for a condom.

Pop this tape in (after adjusting the tracking, naturally), and you're immediately thrown into Brad's (Will Friedle) world. It’s the classic setup: sweet, slightly awkward guy finally gets his chance with the girl of his dreams, Brooke (Marley Shelton). The mood is right, the parents are out... but Brad’s unprepared. No protection. Brooke, wisely, puts the brakes on, sending Brad on a mission that spirals wildly out of control. Forget the gates of Troy; Brad’s battlefield is the suburban sprawl after dark, and his enemies are expired credit cards, gun-toting convenience store clerks, rival dudes, concerned parents, and a whole lot of bad luck.
It's a quintessential "one crazy night" flick, a subgenre the 80s perfected and the 90s gleefully ran with. The plot, penned by Andy Burg and Scott Myers, piles on escalating scenarios, each more ridiculous than the last. Think Adventures in Babysitting meets After Hours, but filtered through the lens of dial-up internet and JNCO jeans aesthetics. It’s predictable in its escalating chaos, sure, but there’s a certain charm to its commitment to the bit.

What really makes Trojan War a fascinating rewind is the cast, a snapshot of faces that were about to be, or already were, everywhere. Will Friedle, deep into his beloved run as Eric Matthews on Boy Meets World, brings that same high-strung, slightly goofy charm to Brad. He’s the relatable anchor in the escalating storm, even when making questionable decisions (like, say, borrowing his dad’s prized convertible).
Then you have Jennifer Love Hewitt as Leah, Brad's supportive best friend who (surprise!) clearly harbors deeper feelings. Hewitt was already a bona fide star thanks to Party of Five and was just about to hit scream queen status with I Know What You Did Last Summer (released the same year!). Watching her here, radiating that girl-next-door warmth while offering Brad often questionable advice, is a nostalgic treat. And Marley Shelton as Brooke is pitch-perfect as the catalyst for the chaos, embodying that slightly unattainable 90s dream girl archetype. Keep an eye out too for familiar faces like Danny Masterson and Lee Majors in smaller roles!


Here’s a bit of "Retro Fun Fact" digging for you: Trojan War was directed by George Huang, who just a few years earlier had made serious waves with the sharp, cynical Hollywood satire Swimming with Sharks (1994). Talk about a tonal shift! Going from Kevin Spacey terrorizing his assistant to Will Friedle searching for latex feels like a studio trying to shoehorn an indie darling into a more commercial box. Maybe that explains the film's somewhat shaky landing.
And land shaky it did. Despite the appealing cast and relatable (if silly) premise, Warner Bros. barely released Trojan War. It reportedly scraped together a measly $309 (yes, three hundred and nine dollars!) at the domestic box office during its blink-and-you'll-miss-it theatrical run. Ouch. It truly found its audience, such as it is, later on home video and cable, becoming one of those "Oh yeah, I remember that movie!" titles discovered during late-night channel surfing or perusing the video store aisles. It's a classic case of a film perhaps mishandled, destined for cult obscurity rather than blockbuster glory. Was the goofy title part of the marketing problem? Who knows, but it certainly didn't scream "teen comedy hit."
Does Trojan War hold up? Well, it depends on your tolerance for 90s teen movie tropes. The humor can be broad, the situations contrived, and the fashion choices... bold. But there's an undeniable earnestness to it. Unlike some of the meaner-spirited comedies that followed, Trojan War has a certain sweetness beneath the slapstick. It captures that feeling of teenage desperation, where a simple setback can feel like the end of the world, or in Brad's case, the start of an unintentional epic.
The practical feel of the film, while not heavy on stunts or explosions like our usual action fare, has that grounded 90s aesthetic. Real locations, tangible props, a world before ubiquitous CGI smoothness. It feels like it could happen, albeit stretched to comedic extremes. The soundtrack pulses with the expected 90s alt-rock and pop, instantly dating the film but also adding to its time-capsule quality.
Justification: Trojan War isn't a lost masterpiece, and its humor hasn't aged perfectly. However, it earns points for its surprisingly stellar cast caught right at pivotal moments in their careers, its earnest commitment to the "one crazy night" formula, and its status as a genuine VHS-era discovery that bombed theatrically. It's a charmingly dated, often silly, but ultimately harmless romp fueled by pure 90s energy.
Final Thought: While not exactly the epic battle its title suggests, Trojan War is a worthy artifact from the late-90s teen comedy campaign – a reminder that sometimes, the most memorable quests began not with a call to arms, but with an empty wallet at the pharmacy checkout. A fun, nostalgic rental, best enjoyed with low expectations and maybe a bowl of popcorn.