This is going to sound strange, so deep breath in, and bear with me. The problem with High Fidelity is John Cusack.
There, I said it. I feel much better now.
You can disagree with me if you want. You’re wrong, but you can disagree. It is physically possible. It’s just not intellectually advisable.
There’s nothing wrong with John Cusack. He was just miscast. I mean, I get how Rob Gordon might seem like the grownup version of Lloyd Dobler, but he’s not even close. Rob Gordon is actually a pretty pathetic guy, but because he’s played by Cusack, some accidental, unintentional coolness is rubbed off. And I get how some underachieving young men might misguidedly put him on a pedestal. Rob is the ultimate fanboy nerd, but he’s the least losery of his friends, the least socially inept. And he puffs himself up by being snobby about his pop culture obsession. Fine. But the thing about Rob Gordon is: he’s not a good guy.
Nick Hornby makes that pretty damn clear in the book, and the character tells us this repeatedly himself in the film: “I am a fucking asshole,” he tells us, but then Cusack flashes those deep brown puppy dog eyes and we feel conflicted. He’s doing and saying pretty shitty things, but it’s Cusack, so he MUST be likable, right?
He’s not likable. He’s an ungrateful little shit. He’s a womanizer with a serious case of (male, as if it needs to be said) entitlement. He skulks about being a rude human being, a stalkery ex, and a very bad boyfriend. But Cusack is such a charmer, and he’s got such a sweet, sympathetic history with cinema, that we ascribe way more positive feelings toward this guy than the character actually deserves.
At one point, when he’s on a self-serving rampage of reconnecting with ex-girlfriends in order to reassure himself that he’s basically blameless, Penny tells reminds him that in fact, HE broke up with HER because she wouldn’t have sex with him (“I wasn’t interested in Penny’s nice qualities, just her breasts, and therefore she was no good to me.”). Her heartbreak led to what basically amounts to rape, and years of sex phobia, and he’s so relieved and satisfied with that answer that he’s spurred to pursue even more ex-girlfriends, never mind the fact that the one right in front of him has just run out of the restaurant in tears. The man is a sociopath and I’m not even kidding. The next ex-girlfriend he visits is thickly mired in depression, and he practically asks us to pat him on the back for not taking advantage of her.

Rob is jealous and possessive and harassing. He is the stuff restraining orders are made of. And he doesn’t even learn a lesson. In the end, the woman who dumped him takes him back because, having just suffered the death of her father, she’s simply too tired, too beaten down by his coersion, to fend him off. That is not a getting back together story that anyone should feel good about, and almost as fast as they can reconcile, he’s off chasing yet another manic pixie fantasy cunt because he can’t even for 10 seconds actually be the nice guy he pretends to be. This is the height of toxic masculinity, but because it’s wearing a cute and cuddly John Cusack body, we fail to see it. We root for him because he’s less of a greaseball than Tim Robbins’s Ian. But being 10% less of a douche doesn’t make you not a douche. It doesn’t make you a nice guy. It doesn’t make you deserving of anyone’s love. Rob Gordon is not a hero. He’s a romantic failure and a social liability and if we made a follow-up to the movie today, he’d be living in his mom’s basement screaming at her to make him some Hamburger Helper as he trashed-talked 12 year olds on League of Legends.