Down to You Is 25, But This Freddie Prinze/Julia Stiles Romance Is a Dumb Teenager at Heart

Youth really is fleeting, even in cinema. The teen-movie boom of the late ’90s and early ’00s had kicked off around the time of the rush-released Scream 2 in late 1997 and was pretty much over by the emergence of Scream 3 in February 2000. In fact, while teen movies from this cycle continued to trickle out in 2000 and 2001 (and the genre had one of its biggest-ever hits when Mean Girls dropped years later), pretty much every touchstone of the Abercrombie-era teen-movie boomlet came out in 1999. This was especially evident when the stars of these movies tried to take baby steps toward graduation in the earliest days of 2000, with the more wistful, grown-up, and dysfunctionally stupid motion picture Down to You. The movie turns 25 this month, but really, it’ll be a dumb, feckless 19-year-old forever.

It seemed like a simple formulation: In January 1999, Miramax released the youth-market rom-com She’s All That, in which the blandly affable Freddie Prinze Jr. romanced Rachael Leigh Cook. It was only natural that in January 2000, Miramax would release the youth-market rom-com Down to You, in which a minutely aged Freddie Prinze Jr. romanced Julia Stiles, who was fresh off the success of 10 Things I Hate About You. In fact, stars from multiple other class-of-99 teen comedies matriculated into the college-set Down to You. Selma Blair of Cruel Intentions plays a MIT dropout who becomes a porn star. Inexplicable Weinstein fave Shawn Hatosy of Outside Providence (and the more widely seen The Faculty) appears as Prinze’s college roommate. In addition, Rosario Dawson plays a cheerful stoner and burgeoning That ’70s Show star Ashton Kutcher has his second-ever film role as a guy who looks and acts like Jim Morrison. His name, in a clever bit of comedy writing, is Jim Morrison.

Maybe Jim Morrison was added later in the production process, which according to one member of a production company that worked on the film, was arduous, expensive, and reshoot-heavy, all based on Harvey Weinstein’s desire to create precisely that She’s All That parallel, turning an “edgy, unorthodox look at a group of friends struggling with post-college life in New York” into a de facto teen comedy without any parents around. I don’t doubt that Weinstein put his greasy meathooks all over this movie, but it’s also difficult to locate any nascent promise in writer-director Kris Isacsson’s first feature that the worst man in the world may have smothered.

Maybe it’s the very fact that this movie was made with so many intensely millennial actors (though in reality, Weinstein’s Choice Prinze was and is solidly Gen-X). It’s theoretically refreshing to see Stiles, Prinze, Blair, and Hatosy playing college-aged kids, advancing more or less in real time from their senior-ish roles in high school comedies. For all the sins of the aggressively plastic and phony aesthetics of the 1999 teen movies, their stars by and large did not labor to remain perma-teens like so many TV stars of the 1990s and 2000s; maybe they absorbed an unconscious lesson from the developmentally arrested Drew Barrymore character in Never Been Kissed. Yet Prinze and Stiles don’t look especially comfortable playing college students, either.

Stiles is an especially bizarre case. With her deep-ish voice and precise diction, she was ideal casting in Ten Things as kind of heightened, sitcommy version of a feminist intellectual, capturing both genuine feminine rage and the teenage poseur inside, fanning those flames. (Who among us, etc.) In Down to You, she attempts to chill out a little: Her Imogen is an aspiring artist, who says things – not coherent or meaningful things, but sentences! – about brushstrokes and the use of color. She smokes pot, albeit not quite on screen. She chats up strangers over her jukebox selection process. She has sex, sort of, if you can call awkwardly pawing at Freddie Prinze Jr. sex. Yet that self-consciousness lingers, emphasizing how Stiles became a teen star in part by appearing vaguely uncomfortable playing teens, and how her particular era of teen movie had so little room for genuine misfits any edgier than a Snapple ad.

Stiles and Prinze split the movie’s woeful direct-camera address duties, with Imogen and Prinze’s Al reflecting on their college relationship some unspecified time after its demise, as they go about their daily business and occasionally usher in flights of fantasy and fancy. (At one point, each one encounters each other as a youngster.) It’s a low-cal, first-love version of Annie Hall, only instead of someone pulling out Marshall McLuhan to put a blowhard in his place, Prinze imagines he’s on The Man Show being chided for being such a cuck when he doesn’t date-rape his girlfriend. Prinze should be good at breaking the fourth wall, if only because it relieves him from the labor of pretending he doesn’t know he’s on camera, the knowledge of which informs almost all of his major performance. He constantly looks as if he’s either going to break out into giggles (and not because his movies are especially funny) or turn to the camera operator and ask a question (and not because his movies are especially complicated). (Credit due: Later, he became a capable voiceover actor, and his onscreen affability appears to be genuine.)

The movie seems to be aiming for a kind of neurotic yearning, but the leads often appear to be gleaning those neuroses off of cue cards. Imogen is mildly commitmentphobic, in the sense that she doesn’t want to get married at 19! Al isn’t certain what he wants to do with his life despite his clear passion for cooking! It’s like they’re begging for 9/11 to hurry up and shatter their charmed Manhattan existences. That tragedy 20 months later didn’t end the scourge of lightweight New York-set romances that seemed to think if they wander around enough parks, they might transform into Woody Allen or Nora Ephron, not by a longshot. But there is, if you’ll permit the stretch, a certain sense of unreadiness around the post-high school, pre-9/11 adventures of Prinze, Stiles, et al. Their movie-star moment had arrived, and they weren’t able to rise to the occasion. Another year later, Stiles had her solo biggest hit with Save the Last Dance, another de facto teen picture; Prinze had another teen-comedy-on-campus romance later in 2000 with Boys and Girls, reuniting with his She’s All That director to no avail, and eventually had a hit franchise with, uh, Scooby-Doo (he’s admittedly well-cast as Fred). Neither would hurt for work after that (Stiles had that steady Bourne supporting gig), but neither of them got much beyond half-measures gesturing at grown-up movies, which were still very much a thing in 2000. Kutcher didn’t make that transition either, but he at least made a few hit movies about grown-ups, seemingly for teens.

It’s precisely the sort of rude awakening that’s supposed to await these characters after graduation, and presumably got more play in Isacsson’s original screenplay, assuming it aimed for a turn-of-the-millennium Kicking & Screaming vibe, or maybe, less lofty but more achievable, a Kevin Smith knockoff. (There’s a lot of pornography in the movie’s plotting, though little sexuality to speak of.) In the final film, it’s as if all the characters have moved into unfurnished apartments and never noticed. Everyone looks a little vacant, their adoring looks perpetually a half-beat behind. But if you can keep its year-2000 context in mind, there’s something weirdly cleansing about Down to You: Here was definitive proof that something from 1999 simply wouldn’t fly just a year later. Much bigger changes were on the horizon, but the youthful ’90s flush of the millennial had rapidly started to drain already.

Jesse Hassenger is associate movies editor at Paste. He also writes about movies and other pop-culture stuff for a bunch of outlets including A.V. Club, GQ, Decider, the Daily Beast, and SportsAlcohol.com, where offerings include an informal podcast. He also co-hosts the New Flesh, a podcast about horror movies, and wastes time on social media under the handle @rockmarooned.