High Fidelity turned 20 this March, which is a sentence I take absolutely no joy in writing. I was 17 when I first saw it, fully in the throws of teenage angst, and John Cusack was one of My Guys. I watched Better Off Dead and Say Anything… almost constantly (the former more than the latter – Say Anything… is actually kind of a bummer), and the prospect of seeing Cusack bemoan his failed relationships while lording over an elitist record store was extremely my shit at the time. (I was exhausting to be around, you guys.) It was a combination of all of my favorite things – mopey introspection, music snobbery, and pining over girls. Consequently, when I walked out of that movie theater in March of 2000, I absolutely loved High Fidelity. Today, I’m considerably older, I’ve been married for several years, and I have way more grey in my hair, and High Fidelity doesn’t play the same as it did back when I was in high school. I’m not positive, but I think I don’t actually like it anymore. Now, don’t get me wrong – the movie is extremely well-made, some of the performances are very good (it’s probably the best work of Cusack’s career, to be honest), and there are some great scenes and very funny bits that still hold up. But time has definitely given me a very different opinion of Cusack’s character.

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Image via Buena Vista Pictures

If you’ve not seen it, High Fidelity is about a record store owner named Rob (Cusack) who gets dumped by his longtime girlfriend Laura (Iben Hjejle) and becomes obsessed with trying to figure out what went wrong with all of his past relationships. He constantly breaks the fourth wall, speaking directly to camera as he makes wry observations and narrates all the chaos in his life. Rob is also obsessed with making lists – he constantly asks his employees Barry (Jack Black) and Dick (Todd Louiso) to name their Top 5 Side 1 Track 1s, or Top 5 Songs About Death. (Rob was way ahead of the curb, successfully predicting the rise of the Internet Listicle.) So he makes a list of his Top 5 Biggest Breakups, the ones that really hurt, and in a scene featuring a truly excellent cameo by Bruce Springsteen, decides to track down all five of his exes to ask them point blank why they broke up with him.

Rob is a self-absorbed asshole, and that’s admittedly intentional. His arc in the movie is figuring out that the problem with all of his past relationships was him, specifically. He focuses entirely on his own needs and rarely does anything to make his partners happy. That’s a fine lesson to learn, and when you’re 17 and you think everything with a modicum of depth is The Deepest Thing Ever, Actually, you’re more than willing to do the movie’s work for it and fill in all the blanks. But the fact is, High Fidelity is only ever concerned with Rob’s feelings. Laura ends up bending over backwards for him in ways that are at best unhealthy and at worst damaging to her own well-being. And Rob does absolutely nothing for her in return. Seriously. By the time the credits roll, the only thing Rob has done to mend their relationship is stumblingly propose to her over a midday beer after nearly cheating on her with a music critic. We don’t ever actually see Rob take any steps to make anyone happy but himself – the climax is Rob begrudgingly accepting a huge gesture from Laura, whose only goal in life is apparently to convince him to love himself, which he already does. He just doesn’t like himself very much, and he’s comfortable being professionally cynical.

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Image via Buena Vista Pictures

There was a narrative in Gen X films of relationships revolving around the preciousness of guys' emotions. That grunged-out loner is an abrasive dick, but he’s got feelings, man, and there’s always an impossibly selfless and endlessly patient woman to chase after him every time the world beats him down. Laura fits that role to a T, so much so that I wonder if the film’s four screenwriters (Cusack included) had ever actually spoken to a woman before writing it.

Laura is a totally insane character. First, she breaks up with Rob for vague reasons that she never really articulates, but that’s the most minor issue, because we can clearly see that Rob is a nightmare to be around, and the reasons behind their breakup become apparent as we see more of their relationship told in flashback. The more baffling question is why she started dating Rob in the first place – she’s a successful lawyer working at a major firm in Chicago who just happened to talk to Rob one night at a club where he was DJing. Meanwhile, Rob is a perpetually angry pop culture elitist who owns a record store wherein his staff regularly bullies any potential customers who don’t share their musical tastes. Despite the fact that she could clearly afford a very nice condo or an actual freaking house in the suburbs, she moves into Rob’s dingy-ass 1 bedroom cluttered with thousands of records that Rob obsessively reorganizes every so often. Because Rob has no desire to leave the space he created for himself, surrounded by everything he thinks is important, and all of his needs must be satisfied before Laura can even begin to think about hers. She says at one point, “I moved in here because I wanted to be with you.” And in a vacuum, that would be a romantic thing to say, but here its just another personal sacrifice the movie expects Laura to make for Rob.

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Image via Buena Vista Pictures

The absolute craziest development of her character is when her father dies and she takes Rob back, literally because she’s too emotionally exhausted to continue with the break-up. Rob storms out of the wake in a blaze of self-pity (this moment is presented as Rob having a major introspective epiphany, but it’s really just another excuse for him to feel sorry for himself), and Laura chases after him in her car, putting all of her needs aside to rescue him from himself yet again. She actually says, “I’m too tired not to be with you” before asking him to have sex with her to distract her from the agony she’s feeling. That’s their big reconciliation. And then she’s totally fine and bubbly and never mentions her father again for the rest of the film. High Fidelity literally could not come up with a reason for Laura to take Rob back, so they decided on making her too emotionally weak to resist him any longer. Hooray.

There are worse aspects to Rob than his self-absorption. He spends the majority of the movie as the embodiment of toxic masculinity. He shouts, curses, kicks things, and generally has a terrifying meltdown every time he gets dumped. And he’s incredibly possessive of women. All he cares about with Laura is whether or not she’s slept with Ian (Tim Robbins), the guy she moved in with after they broke up. Then when she admits that she has, he storms off like a kid and makes her chase after him, because once again, Laura must drop everything to soothe his hurt feelings. (In fact, that’s the entire premise of the movie – Rob holding women hostage until they make him feel better about getting dumped). Then he finds Ian’s address, shows up at the apartment and starts calling them over and over again until Laura agrees to speak to him. He’s harassing his ex-girlfriend with no respect for her boundaries.

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Image via Buena Vista Pictures

Finally, there’s an entire plot point about how Rob doesn’t understand consent. We see in a flashback to Rob’s teenage years that Penny (Joelle Carter), one of his Top 5 ex-girlfriends, has to repeatedly push Rob's groping hands off of her, until Rob finally dumps her for being too “tight.” And when he meets up with Penny as an adult to demand why she refused to have sex with him, she tells him that she was crazy about him and just wanted to wait to have sex until she was older. She then tearfully reveals that she was date raped by the next boy she went out with and that that the experience ruined her view of sex, and Rob doesn’t hear any of it. All he hears is the reminder that he actually broke up with her, and he’s delighted. He can cross Penny off of the list of his Greatest Heartbreaks because she was the one who actually got her heart broken, not him. He doesn’t show any remorse, which the movie intends as a joke about his extreme self-absorption, but it’s hard to find his cold selfishness funny now that I’m older and not a shitty know-it-all teenager with a terrible idea of what adult relationships are supposed to be like.

High Fidelity is a difficult movie to defend. There’s a lot to like about it, although most of the good parts can be summed up with the phrase “every scene with Jack Black and Todd Louiso,” who absolutely steal the movie as Barry and Dick. (This was Black’s breakout role, and he tears through every scene with magnetic, impish energy.) And Cusack does his considerable best to distract you from the fact that Rob is a cruel, miserable villain. But the movie’s primary offer of “horrible guy doesn’t realize he’s horrible” has become dramatically less funny in 2020, long separated from the accepted romantic comedy tropes of the 1990s. It’s hard to laugh at a guy emotionally terrorizing his ex-girlfriends, even when interspersed with Jack Black doing an exaggerated dance routine to “Walking On Sunshine” by Katrina & The Waves.