25 Years Ago, Keeping the Faith and High Fidelity Tried to Remake the Romantic Comedy for Grown-Ups

By Jesse Hassenger  |  April 14, 2025 | 9:15am
Movies Features Edward Norton
25 Years Ago, Keeping the Faith and High Fidelity Tried to Remake the Romantic Comedy for Grown-Ups
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It’s not uncommon to look upon the late ’90s and early ’00s as a boom time for big-studio romantic comedies based on sheer frequency. But that abundance could also be a curse, subjecting the genre to the whims of big stars in super-sized, almost franchise-y gimmickry like Runaway Bride (the non-sequel to Pretty Woman reuniting Julia Roberts and Richard Gere) or What Women Want (a Nancy Meyers rom-com with a superpowered Mel Gibson); even You’ve Got Mail, one of the best of its era, was basically Hanks/Ryan III. The truth is, the early 21st century romantic comedy has never been on especially strong footing, especially compared to the turn of the previous decade, when When Harry Met Sally and Say Anything set two very different high-water marks for the genre in 1989.

Speaking of Say Anything: There are a couple of images that linger with anyone who’s seen Cameron Crowe’s directorial debut a few times. One is star John Cusack, as lovelorn teenager Lloyd Dobler, walking around in the pouring rain, occasionally making pay-phone calls from the wet streets of Seattle. Another, seen on posters everywhere, has Cusack hoisting a boombox on the lawn of Diane Court (Ione Skye), the brainy dream girl who has broken things off with him. He’s playing “In Your Eyes” by Peter Gabriel, a song that was playing when they first had sex in his car.

There’s been some post-millennial debate about whether all this business, particularly the boombox-hoisting, is genuinely romantic or the actions of a troubled stalker. (An episode of How I Met Your Mother memorably described it as the divide between “Dobler and Dahmer,” largely dependent on whether you already liked the person making the grand and/or creepy gesture.) So it’s remarkable to see how frequently that material is echoed and tacitly critiqued, even before the golden/nightmare age of internet discourse, in High Fidelity, another Cusack rom-com (of sorts) that trailed Say Anything by 11 years and took the rom-com a different direction in the spring of 2000. In the later film, Cusack plays lovelorn adult Rob Gordon, a character adapted from Nick Hornby’s London-set comic novel, who in the film adaptation spends a lot of time pining away in the rain (this time on the wet streets of Chicago), and essentially carries that boombox around with him in his head, in his very soul. Even if he’s not literally playing songs from his past relationships out loud on a portable stereo, Rob works at a record store, walks around with headphones on, and spends a chunk of the movie in his apartment, arranging his record collection not by genre, not alphabetically, but “autobiographically.” Say what you will about playing “In Your Eyes” on a girl’s lawn; it would certainly make that autobiographical filing of Peter Gabriel’s So LP a lot clearer.

High Fidelity isn’t the first movie to function as an alternate-reality companion to Say Anything. The previous movie that Cusack co-wrote with his pals D. V. DeVincentis and Steve Pink, Grosse Pointe Blank, plays like a what-if sequel: What if Lloyd’s break-up with Diane stuck, and he did actually go work for the army, despite his stated objections? What if he then became a contract killer and came back into town for his 10-year high school reunion? Rob Gordon from High Fidelity is less directly Lloyd-coded in his mannerisms and preoccupations, not least because Rob Gordon is an asshole. (Lloyd Dobler, even if he oversteps his bounds, is essentially not.) But he does mope in the rain a bunch, and the movie’s cast includes Say Anything alumni Joan Cusack and Lili Taylor. (Jack Black makes Rob’s obnoxious employee Barry very much his own in a star-making turn, but how crushed Jeremy Piven must have been to not get the part!)

So it’s easy enough to think of High Fidelity as a grown-up rom-com companion/B-side to the idealism of Say Anything; it’s a movie about learning to conduct relationships like an adult rather than living in your top-five lists and looking around eagerly for the next fantasy to match them. But as a romance, High Fidelity becomes a victim of its own observant, rueful comedy; it’s too realistic about Rob’s man-boy immaturity, too aware of how ridiculous he looks out there doing the Dobler rain-soaked self-pity routine, to conjure true romantic illusion.

This tactic would become a more active cliché of American comedy in the decade that ensued: the rom-com so pleased with its novelty in attending to a belated male coming-of-age narrative that it forgets to much bother with the woman in the picture. High Fidelity doesn’t really neglect Laura (Iben Hjejle); she’s an utterly believable and dimensional character, helped even more in retrospect by Hjejle not being a big American movie star, and the movie is more willing to get under the skin of the kind of guys it’s about (which still won’t stop it from being misread by some of those same guys). But it’s an object lesson in how dimensionalizing and complicating a romantic comedy can sometimes turn it into something else, for better or for worse. Then again, maybe High Fidelity only seems tenuous within its genre because how ritualized most romantic comedies had allowed themselves to become at this point.

A couple of weeks later, Touchstone Pictures, the studio behind High Fidelity (and Pretty Woman, for that matter!) followed it up with a more traditionally-minded romance, though still out of step with the most popular rom-coms of the day. Edward Norton’s Keeping the Faith is an unusually gentle and potentially cornball version of a situationship, acknowledging its bar-joke origins by having Norton literally stumble into a bar to tell his story of a priest and a rabbi, both in love with the same woman. Norton plays Brian, the priest; Ben Stiller plays Jake, the rabbi; Jenna Elfman plays Anna, their mutual childhood friend who returns to New York as a glamorous career woman. Adult Anna likes them both, though she falls in love with Jake; lucky her, given that he’s the one actually permitted to marry by his profession.

The biggest sign that Keeping the Faith is from the year 2000 is that, again, Jenna Elfman plays Anna (and though it’s easy to see the sitcom-trained Elfman as the weak link here – I mean, I’ve seen this movie half a dozen times, and she unquestionably is – it’s also telling about Hollywood’s short fuse for leading ladies that 25 years later, Norton and Stiller remain big names, while Elfman recurs on Tim Allen’s latest warmed-over sitcom). Otherwise, beyond a few nascent references to digital tech (an old lady wants to do her emails! Sassy! And of course, Anna is attached to her pre-smartphone work device; again, it’s a world where answering emails is considered a character trait), the movie could slide around the calendar and land virtually anywhere from about two decades before its actual release. Norton, then known as an intense potential heir to the likes of Robert De Niro or Al Pacino, not only plays the sweeter, more innocent Brian but directs his first movie as sort of a Woody Allen Lite love letter to Manhattan. (Norton has done some form of a Woody impression in multiple movies, and this was well before Allen fell out of favor as an obvious reference point.)

Two things make Keeping the Faith more than a cutesy joke told at length: First, Norton, as an actor and director, has a nice feel for infatuation, both requited and not. Even if you don’t react to Elfman’s performance like she’s Rosalind Russell or Audrey Hepburn or Geena Davis, Norton captures the feeling of getting all moony-eyed over someone special (and how beautiful New York can look as a backdrop to those feelings). Second, the romantic obstacles provided by screenwriter Stuart Blumberg are just right: Not so insurmountable that they push the movie into melodrama, and not so easy that they feel like dopey contrivances. Stiller’s Jake is expected to marry a Jewish woman, and Norton’s Brian must struggle with the conflicted feelings Anna’s reappearance inspires, whether or not he actually has a shot with her. Though the premise sounds like a hoary punchline-forward concept, the movie itself puts its relationships first.

Keeping the Faith would prove even less influential than High Fidelity, which wasn’t a big hit but did anticipate some Judd Apatow-type shenanigans on the horizon. The biggest romantic comedy of the following year was America’s Sweethearts, which plugged Cusack into the big-star mechanics opposite Julia Roberts. (They didn’t particularly click.) Sweet Home Alabama, the most popular big studio rom-com of 2002 (because My Big Fat Greek Wedding was actually an indie, and surprisingly conflict-averse to boot), almost feels like a rebuke to the pro-city, Updike-quoting Keeping the Faith. How to Lose a Guy in 10 Days would follow in 2003, locking in the genre’s image as starry, soft-focus, sitcommy imitations of what used to be screwball farce. For a few weeks in the spring of 2000, the rom-com flirted with growing up for the new century, until big studios and stars pressed forward with heartbreak.

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.

 
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