10 Y2K-Era Teen Comedies You Probably Forgot About

After American Pie recouped its $11 million budget more than 20 times over, Hollywood seemingly made putting teens front and center of the multiplex a priority: It felt like you could see a new R-rated comedy—typically involving sex-obsessed students, gratuitous nudity (nearly always female), and enough gross-out gags to make the squeamish, well, gag—every week.

But while the likes of Road Trip and Not Another Teen Movie managed to ride on American Pie’s pastry-smeared coattails, others completely stiffed. As one of the biggest losers celebrates its 25th anniversary, here’s a look at 10 Y2k teen movies you probably forgot all about.  

1. Loser
2. Sugar and Spice
3. Whatever It Takes
4. Slackers
5. Detroit Rock City
6. Coming Soon
7. Harvard Man
8. Outside Providence
9. Sorority Boys
10. Boys and Girls

Loser

Loser by name, loser by nature. This turn-of-the-century flop should have been a home run: It was written and directed by Amy Heckerling, who was responsible for launching Alicia Silverstone in the teen classic Clueless. It starred two castmates from American Pie. And it boasted the era’s biggest slacker anthem, Wheatus’s impossibly infectious “Teenage Dirtbag.”

But the icky love triangle between Jason Biggs’s small-town boy, Mena Suvari’s street-smart student, and Greg Kinnear’s predatory professor failed to connect, and instead of topping the box office, Loser crawled in at No. 8. Heckerling’s agent later placed the blame on the film studio, which—missing the point of the raunchy teen comedy—had insisted on obtaining a toothless PG-13. 

Sugar and Spice

According to Gabrielle Union, she and a number of her Bring It On co-stars auditioned for, but didn’t get, roles in 2001’s Sugar and Spice. “Bring It On was the cheerleading movie that was the consolation prize because you didn’t get the cheerleading movie that you wanted,” Union said.

Of course, the film she auditioned for was very different from the finished product. In fact, screenwriter Lona Williams was so disillusioned with how her original script had been butchered that she insisted on using a pseudonym. Inspired by a real-life crime wave in Houston two years earlier, the dark comedy centered on a pregnant high school cheerleader who, alongside her fellow pom-pom shakers, turned to armed robbery. But neither its story nor its satire really hit the mark.

Whatever It Takes

In the late ’90s and early 2000s, teen movie adaptations of great literary works were all the rage—so it’s no wonder that writer Mark Schwan and director David Raynr attempted to put a similar Y2K spin on Edmond Rostand’s 19th-century romance Cyrano de Bergerac. Despite three coveted Teen Choice Awards nods (including Choice Movie Sleaze Bag and Choice Movie Hissy Fit), Whatever It Takes didn’t exactly do its source material justice: With flat TV movie visuals and a predictable script that occasionally bordered on the misogynistic, the 2000 misfire was almost entirely devoid of charm. 

Slackers

Flatulent roommates, penis sock puppets, septuagenarian sex workers getting sponge baths—it’s no surprise that Roger Ebert delivered one of his most scathing reviews for 2002’s little-seen Slackers: “Not a sexy, erotic, steamy, or even smutty movie, but a just plain dirty movie. It made me feel unclean … This film knows no shame.”

Starring Jason Schwartzman as a delusional creep who blackmails a group of college cheats into engineering his dream date, Slackers was a box office disaster, spending just two weeks in theaters after missing the Top 10. The juvenile comedy—which should not be confused with Richard Linklater’s similarly-named Slacker—is as lazy as its protagonists. 

Detroit Rock City

While most Y2K teen movies were set in the present day, the 1999 film Detroit Rock City threw things back to the 1970s—specifically, the period when KISS reigned supreme. The film, which was co-produced by frontman Gene Simmons himself, is as much a love letter to the flamboyant glam rockers as a nostalgic comedy: Its four heroes, who are in a tribute band, embark on an increasingly debauched road trip to see the real thing. Although hardly a masterpiece of the genre, its talented cast—including Melanie Lynskey and Natasha Lyonne—affectionately captures that phase when music is the only thing that truly matters.

Coming Soon

Chances are, you’d have heard much more about Coming Soon had its three leads been male horndogs rather than orgasm-chasing prep school girls (Bonnie Root, Gaby Hoffman, and Trivia Vessey star). The progressive sex comedy ran into numerous troubles securing an R-rating; the Motion Picture Association of America took issue with its depictions of female sexuality and rated it NC-17 twice. “It’s so easy to market guys wanting to get laid and girls getting talked into it, but the idea of teenage girls actively looking for it is unusual,” writer-director Collette Burson said in 1999. “There is a demographic that doesn’t respond to this theme, and that’s 40-year-old men with teenage daughters. It makes them very uncomfortable.”

The double standards were called out, but by the time Coming Soon trickled into just two theaters in 2000, the initial buzz was long gone. The little-seen coming-of-age film boasts before-they-were-famous turns from Ashton Kutcher, Ryan Reynolds, and Ellen Pompeo, and remains the teen movie explosion’s hidden gem. 

Harvard Man

Inspired by the now-Me Too’d writer-director James Toback’s acid-fueled experience at the titular institution, 2001’s Harvard Man certainly has a novel premise: a college basketball star throws a game to help rebuild the family home destroyed by a tornado, only to face existential crisis on a nightmarish LSD trip. And that’s not even mentioning the love triangle involving Sarah Michelle Gellar as the daughter of a mafia boss and Joey Lauren Adams as his professor. But the constant visual hallucinations, wild shifts in tone, and pretentious philosophical musings make what sounds like a fun ride on paper an incoherent slog on screen. 

Outside Providence

Because he was busy making There’s Something About Mary, grossout master Peter Farrelly had to pass the directorial reins for the adaptation of his 1988 novel Outside Providence to Michael Corrente (who co-wrote the screenplay alongside Farrelly and his brother, Bobby). That might explain the distinct lack of bodily fluids in this surprisingly sweet blend of stoner comedy, fish-out-of-water drama, and teen romance. Shawn Hatosy’s pot-obsessed slacker Dunph is at the center of all three when he’s sent to an elite boarding school after one Cheech and Chong-esque escapade too many. There, he connects with the “coolest girl in school,” incurs the wrath of a vengeful dorm master, and learns that the privileged kids are just as messed up as the unprivileged ones. 

Sorority Boys

The 2002 gender-swapping comedy Sorority Boys is a film that certainly wouldn’t pass muster today: Three frat bros accused of stealing from their house’s treasury dress up as women and go to ladies’ night at the frat so they can retrieve a videotape that will reveal the identity of the real thief. Despite their unconvincing wigs and badly covered sideburns, the trio somehow manages to hoodwink their fellow students and their own families into believing they’re the genuine article. The film, which is directed by Wallace Wolodarsky—a co-writer of vintage The Simpsons episodes—is a witless caper that pushes the boundaries of credulity and engages in blatant misogyny, homophobia, and TERFism.

Boys and Girls

Director Robert Iscove was undoubtedly hoping to strike lightning twice with 2000’s Boys and Girls, his follow-up to She’s All That. He reunited with Freddie Prinze Jr., shoehorned in another big dance sequence, and again argued that drop-dead gorgeous looks can be masked by a simple pair of spectacles. This time around, however, he made his leading man the awkward nerd in a Serendipity-meets-When Harry Met Sally tale as generic as its title. There’s nothing particularly objectionable about Boys and Girls, which tells the story of two UC Berkeley students continually thrown together via various intermittent meet-cutes. But severely lacking in chemistry, characterization, and comedy, it’s a pale imitation of former glories. 

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