I recently dissected my romantic history in the context of the film Beautiful Girls. Readers are thus aware I had two serious college girlfriends, one of whom I dated freshman year; this was 1984-85.
She spent the spring break of what was her sophomore year in either Manhattan or East Hampton – where she saw a newly-released film called The Sure Thing. Directed by Rob Reiner – fresh off the critical and commercial success of the previous year’s This is Spinal Tap – it effectively begins at an unnamed Ivy League college in New England.[1] Walter “Gib” Gibson, a freshman who has lost his sexual mojo, is lured to Los Angeles over winter break by his friend Lance (Anthony Edwards, who had achieved fame in the previous year’s Revenge of the Nerds) by the promise of a sexual “sure thing”: “No questions asked, no strings attached, no guilt involved.” Accompanying Gib on what turns into the cross-country trip from hell is Alison Bradbury, a Type-A student the polar opposite of Gib, a bright but unmotivated student who gets pepperoni stains on his last-second English assignments.[2] Alison’s uptightness is apparent when she declares without irony, “Spontaneity has its time and its place.” She wants to spend the winter break with her more-uptight boyfriend Jason (Boyd Gaines). Shenanigans and hijinks ensue, resulting in a satisfying denouement. In many ways, The Sure Thing is an updated version of It Happened One Night featuring genuinely likable 80s college kids.
Gib is played with manic charm by an 18-year-old actor in his first starring role: John Cusack. In one of her first starring roles, 22-year-old Daphne Zuniga matches Cusack – with whom she has palpable chemistry – line for line, hammer for tongs. Sophomore-girlfriend was so taken with the movie, she took me to see it after the break. It immediately became one of my handful of favorite movies, one I watched repeatedly over the next decade-plus.
Cusack is only three months and two days older than me, and I too was a freshman at an Ivy League college in New England (Yale). We both had dark-haired, slender, slightly-offbeat good looks – even if I am four inches shorter, my eyes are brown (not green), and he knew exactly what to do with his hair – or someone did.

By contrast, I clearly had no clue what to do with my unruly mop of curly – though I insisted it was “wavy” – hair, adopting the “helmet hair” approach.

It is not a stretch, then, that sophomore-girlfriend saw a good deal of me in Gib, even if I never once got a pepperoni stain on an English assignment. My highly-driven girlfriend had superficial similarities to Alison – let us leave it at that.
This was the start of my man-crush on John Cusack, which lasted through a string of romantic comedies in the 1980s, culminating in his breakout performance as Lloyd Dobler in Say Anything, then into adult roles in the 1990s, beginning with small-time conman Roy Dillon in The Grifters and peaking with his other iconic role – professional assassin Martin Q. Blank in Grosse Pointe Blank. Two years later, Cusack played Nelson Rockefeller in one of my favorite movies, Cradle Will Rock; that same year he appeared in two other movies: the forgettable Pushing Tin – and one of my least favorite movies, the painfully-overrated Being John Malkovich. All told, I have now seen 29 films in which Cusack appears – even if only briefly – including 21 in which he could be considered one of the film’s “stars.”[3]
That said – and as scrupulously as I avoid saying anything negative in these essays – I so loathed Being John Malkovich, it began to affect how I viewed Cusack. Nonetheless, I was excited the following April to go with the woman my wife Nell calls “my first wife” to the Showcase Cinemas in Woburn, Massachusetts to see him star in High Fidelity, an adaptation of the popular Nick Hornby novel of the same title.
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High Fidelity should have become one of my favorite-ever movies. It starred Cusack as a city-dwelling used-record-store owner named Rob Gordon who obsesses over his impressive record collection – at one point organizing them autobiographically, which is a little bit of brilliant – and compulsively makes “top-5” lists and mixtapes. Does this sound like anybody we know?
Instead, however, I was so underwhelmed – upset, even – by High Fidelity that between it, Being John Malkovich and a few other less-appealing films, I stopped going to the theater to see John Cusack films; I still bought the Cradle Will Rock DVD a few years later. It was only two years ago that I finally watched a Cusack-starring film released after March 2000: 2001’s Serendipity. While I now find “destined-true-love” films highly problematic – thus the essay I reference above – I can easily rationalize how much I like this film (and Beautiful Girls, for that matter).
This past Saturday night, meanwhile, it was my turn to pick a movie for family movie night; my previous choice had been the entertaining and eerily-prophetic Pump Up the Volume. Having returned to my music-ranking spreadsheets and Dadaist lyrical poetry – and having finally seen and enjoyed 1408 – I surprised myself by choosing High Fidelity. I was ready to give it a second chance, and, if nothing else, Nell and I reasoned that it featured great music and a breakout performance by Jack Black, whom our children loved in School of Rock.
It started out well enough – but then our younger child caught their older sister looking at her iPhone under her comforter, so they asked if they could look at their iPhone as well. Normally, I would not care – but then older daughter lied about being on her phone, and I became irritated. We took a short break while we decided whether to continue watching, and I thumped into the kitchen to load the dishwasher.
The truth was that I was deciding if I wanted to keep watching – the film was making me extremely uncomfortable. High Fidelity’s framing device is Rob’s top 5 most painful and humiliating breakups (read: “times I was dumped”); Cusack spends much of the movie breaking the fourth wall to detail these particular grievances, among others. The breakup list was inspired by Laura (played wearily by Danish-born Iben Hjejle), Rob’s exceptionally-patient girlfriend, leaving him and slowly moving out of their shared Chicago apartment. After some mental tussling, Rob puts Laura at #5 on his list, which is in reverse chronological order, in an act of pure spite.
In dissecting these breakups, Rob engages in something akin to interrogating memory. Except that, rather than approaching the task with requisite humility and careful attention to detail, Rob explores the not-very-distant past – 33-year-old Cusack portrayed a character meant to be about 30 – with whiny narcissism and woe-is-me petulance. This helps to explain why, maybe 30 minutes after the four of us resumed watching it, our older daughter proclaimed, “I like the movie just fine, but I hate Rob.” She later called him a misogynist. I assured her there was a redemptive arc, but it was ephemeral, if it was there at all.
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To understand my antipathy toward this film, which is clearly a great work of art to inspire such a visceral reaction, we need to revisit my life in the spring of 2000.
First-wife and I had been dating for almost seven years, living together for almost five. We had become a single-name couple – MattandName – and friends and relatives likely assumed it was simply a matter of time before we turned a de facto marriage into a de jure one. Except that I had no desire to marry anyone: I once awoke in a cold sweat after dreaming we had married after 10 years of dating.
Meanwhile, I had settled into my third position in my new career: health-related data analyst and project manager. It is glorious irony this job ultimately ended my “first marriage.” That September, I met a woman on yet another trip to the corporate office in Ann Arbor, Michigan…but that is an entirely different story.
After a rough start to 1996, first-wife and I had settled into a good groove. I was, broadly speaking, happy with her – she was brilliant, funny, kind, attractive and endlessly patient with me.
But the “groove” was really a “rut,” though “lazily contented” might be better. Actually, no, the word I want is “stagnation.” At some point during the previous 10-15 years, I had ceased to move forward emotionally; this did not truly change until my mother died four years later.
Cusack’s Gordon was simply expressing what I was suppressing, out of fear of disrupting a comfortable, yet unfulfilling, life. Rob embodies the generational ennui of someone who, like me, was born on the cusp of the Baby Boom and Generation X, though I much prefer what Morgan Richter calls the latter: the MTV Generation. MTV first arrived in my suburban bedroom around 1982, and I did not really turn it off until I left for college two-plus years later. And it was not just me: during my sophomore year at Yale one of my two roommates was asked about a new song; he responded that he had not seen it yet.
Now somewhere between our mid-20s and mid-30s as the new millennium approached, we had become disillusioned that the glide path into successful adulthood we expected after college graduation had stalled somewhere. Or maybe we were trapped at the top of a Ferris wheel, or on a stopped carousel, or whatever “that thing we want is just out of reach and we are unable to move to get it” metaphor you choose.
But it is not simply generational ennui that Rob is experiencing.
I interpret his emotional turmoil as undiagnosed clinical depression; the thing first-wife showed such patience with was how my own undiagnosed clinical depression manifested itself in mercurial and at-times paranoid behavior. Desk-chair diagnosing is generally unwise (though Noralities does it very well here), but the signs are there: chronic exhaustion, irritability, mood swings, a loss of interest in things once loved, excessive alcohol consumption, overwhelming existential gloom and circular dwelling upon trivia that leads nowhere; the metaphoric Ferris wheel and carousel may be moving, after all. At one point, Rob claims he is so sick of his record store – clearly successful enough for him to purchase hundreds, maybe thousands, of records – he wants to sell it then work in a Virgin megastore, dating this film perfectly.[4]
That is what clinical depression sounds like: “I am in so much anguish, even the unquestionably good parts of my life take too much energy to deal with.” Rob is asked – I believe by mutual friend Liz (played with fierce tenderness by sister Joan Cusack) – why he wants Laura to be his girlfriend again. He never really answers the question,[5] so I conclude she is the only thing standing between him and fully succumbing to his depression (and, it is implied, having little-to-no-income). This is precisely where I was with first-wife: she had become my security blanket, emotionally and financially, and I now realized I resented the hell out of her for that. Marriage under these conditions would have been an absolute disaster – so it is for the best our relationship ended reasonably-amicably within a year.
This is at least partly why High Fidelity left such a bad taste in my mouth. In the cinematic version of Rob Gordon – portrayed by my celebrity man-crush – I saw far too much of myself than I cared to admit. The obsessive record-collector, list-maker and mixtape-constructor. The emotional and professional stagnation. The not-quite-alcoholism – I once angrily and tearfully poured most of a bottle of not-cheap Fonseca port down the kitchen sink in reaction to my behavior after drinking too much. The wild mood swings. The desperate attempt to find something – for me it was late night diner runs, the Phillies, crushes on coworkers – that would trick my brain into releasing sufficient quantities of serotonin.
[SPOILER ALERT]
But what truly irritates me about High Fidelity is its ending. A flashback scene in which Rob is DJing in a local club, what he describes as the happiest time of his life, shows Laura meeting Rob. I conclude it was this happier version of Rob with whom Laura fell in love; only later did Rob’s undiagnosed depression reassert itself and drive a wedge between them. First-wife and I followed a similar trajectory: I was in a good place professionally and emotionally when we met in June 1993, though that slowly unraveled until I landed my first professional data analysis position in October 1996, which was also when I made a conscious decision not to pursue a different relationship.
Except: I did eventually pursue a different relationship. If I learned how to be in a long-term, cohabiting relationship being with first-wife, Ann-Arbor showed me what “I want to spend the rest of my life with you” meant – even if, for better or worse, she and I did not. As I explained to older daughter in the context of what I was writing in this essay, I could not have married her mother without everything I learned from first-wife and Ann-Arbor.
But that is not how High Fidelity ends. Instead, Laura, who seems only half-heartedly to have left Rob, invites him – not her current boyfriend – to her father’s funeral; she had yet to tell her family she had left Rob…
…and as I write these words, it dawns on me that Laura was essentially giving Rob an ultimatum: I do not want to leave you, but I cannot remain with you the way you are. This is the ultimatum first-wife never gave me, perhaps she knew – or suspected – what the outcome would be.
After showing minimal emotional maturity for the first time in the film – telling Laura “I’m sorry” (it is unclear if he is offering sympathy or apologizing for his behavior) – Rob ducks out of the post-funeral party at Laura’s parents’ house into the pouring rain. Laura chases after him as an excuse to leave the house – then has sex with Rob in the front seat of her car as a way to “feel something, anything.”[6] She wants to go home with Rob, and much to Rob’s (and, frankly, our) surprise wants to be with him again. This sequence of events is incredibly jarring given how hard Laura had just worked to get out of the relationship.
The movie ends with Rob, launching a new side career as a record producer while DJing at his old club. Laura has moved back in to Rob’s apartment, he is still running the store – and Rob stops himself from making a mixtape for an attractive (and attracted to him) music writer. This is a comically-awful ending in that Rob appears to face zero consequences for his terrible behavior.
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There is one other way High Fidelity irritates me – the way in which Rob’s character learns nothing from his misguided efforts to “interrogate memory,” actively revisiting each woman in an attempt to understand why he is so monumentally unlucky, or something equally self-pitying.
The first relationship apparently lasted only six hours when he and she were 14 years old – they kissed after school under the bleachers for two hours. After three days of this, she started kissing another boy under the bleachers – leading a male friend to call her a slut in a perverse form of male bonding. Rob calls this girl’s mother – only to learn she married the second boy, considering him “her first and only boyfriend.” After obnoxiously insisting that he – Rob – was her daughter’s first boyfriend, the mother abruptly ends the call. Rob then jubilantly exults that because she married other-boy, he is somehow not responsible for the end of the relationship. As someone who has been the final boyfriend before the husband on multiple occasions, this reaction makes zero sense to me. Dude, she dumped you for the boy she ultimately married. That is harsh, not exculpatory.
His reaction to the second woman is even worse. Rob had dated a woman in high school who genuinely liked him, but she would not let him go beyond kissing. Rather than respect her boundaries, he quips, “Sometimes I got so bored of trying to touch her breast that I would try to touch her between her legs. It was like trying to borrow a dollar, getting turned down, and asking for 50 grand instead.” This was an extremely uncomfortable scene to watch with our two children, as it laughs off a form of sexual assault. Rob cruelly breaks up with her, only to learn she had sexual intercourse with a classmate shortly thereafter, infuriating him.
What we learn over a cringe-inducing dinner, however, is that a) she would happily have slept with Rob when she was ready, b) their classmate raped her in spirit if not in deed, c) rather than enjoying a healthy sex life in college, the trauma kept her celibate those years and d) “You broke up with me!” She then storms out of the restaurant – leaving Rob, who has somehow absorbed none of this, to exclaim with delight, “That’s right, I broke up with her!”
Readers of Interrogating Memory will recall a sequence of stories in Chapter 10 (Night Driving) leading up to my high school senior prom, after which I write:
Shortly after the prom, I abruptly stopped seeing Lower-Merion-girl—I forget why—though she had been nothing but kind to me. I had also hurt a close and loyal friend. I could have asked quiet-blonde to go with me before agreeing to go with first-girlfriend. And then there was brunette-junior, but I was too timid even to talk to her, let alone ask her to the prom. No matter how you slice it, I was a complete schmuck.
This, in a nutshell, is what interrogating memory is supposed to look like: an honest and objective appraisal of the past, sometimes leading to sincere apologies for any pain one has caused – as I did years later. But when Rob hears a heartbreaking tale of sexual assault and trauma – one his own selfishness helped to initiate – his narcissism only allows him to process that he dumped her, so that is that. I am a little sick to my stomach recalling this moment. Her “Fuck you, Rob!” as she does what I screamed at the television for Laura to do – get the hell out of there – feels woefully insufficient.
I will not belabor the other two women, other than to note Rob rings variations on the theme of “they were awful people; thank goodness I got out when I did.” To be brutally honest, I too have revised my opinion of women after the fact to soften the blow of being dumped by them, but never to this extent. And while I tried to learn something from the end of every relationship, Rob appears to learn nothing.
Instead, Laura – whose character is a bit too good to be true, perhaps to emphasize how despicable Rob is – takes him back out of what feels like desperation, possibly due to situational depression. And rather than force him to mend his ways – psychotherapy would be an excellent start, and I envision him selling most of his record collection to pay for it and the $4,000 she lent him – he has actually gone backwards to DJing, not forward to something entirely new. They have simply fallen back into their rut…and it will not end well unless Rob finally grows up and accepts responsibility for his actions – and learns to treat women as something other than another topic for his lists.
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As I wrote this unusually personal and vitriolic essay, I rewatched The Sure Thing. Despite having seen it multiple times, though not for at least 20 years, it was even better than I remembered. It is an utterly delightful film, and its sunny charm was the perfect antidote to the dark narcissism of High Fidelity. Unlike in the latter film, in which only the Zen-seeming Dick (Todd Louiso) appears to learn anything or grow emotionally, both lead characters in The Sure Thing mature in remarkable, yet realistic, ways. Gib, having fallen mutually in love with Alison – and having endured a great deal to reach this point – hesitates to have sex with his unnamed “sure thing” (played with naïve sweetness by UK-born Nicollette Sheridan in her first film role), sagely remarking to Lance, “I’m 19 years old…maybe I’m too old for this.” In less than one week, Gib has matured more than Rob Gordon does over his first 30 years. Alison, meanwhile, nurtures her rebellious and playful side…discovering that rigid perfectionism is not living, it is barely even existing. Contrast this with Laura, who is presented as a kind of dream woman, requiring no effort at all: an adult relationship version of a “sure thing.”
But The Sure Thing literally saves the best for last, just before the camera pans up to end the movie with a mirror image of the starry night sky which opens the film. Alison and Gib kiss atop the library, the scene of their awful first date. Outside of falling asleep one night in each other’s arms, this is the first intimate contact they have had – upending any expectation this is a raunchy teen sex comedy. And unlike the doomed carousel on which Rob and Laura continue to ride, it is gloriously ambiguous where – if anywhere – their relationship will go.
It is not a sure thing, which is precisely how it is supposed to be.
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[1] It was filmed at Cornell University in Ithaca, New York.
[2] Alison – were The Sure Thing made in the 2020s – would likely have an eating disorder. I write this from tragic personal experience.
[3] According to the Internet Movie Database, this is most for any actor, beating out Humphrey Bogart (24), Michael Caine (23) and Jack Lemmon (17), among others.
[4] In 1996, when I was struggling to find a new position, I considered writing a book based upon my revised version of a recent “Alternative 500.” It took two decades, psychotherapy and prescribed anti-depressants, but I finally became a full-time writer. I might even earn some money from it someday.
[5] He does make a top five list about things he misses about Laura, but he ruins it by noting he could also “do a top five things about her that drive me crazy but it’s just your garden variety women you know, schizo stuff and that’s the kind of thing that got me here.” There is a term for lumping all women together under the pejorative “schizo”: misogyny. He also insists that while he gets tired of many things, and that his gut has “shit for brains,” he never gets tired of Laura, but in the context of his character, this is very weak sauce indeed.
[6] This reads like situational depression to me.
What a great way to explain how many of us decide to look back on our younger selves. Nostalgia isn’t what it used to be! Totally relatable and a perfect critique of the film. I too, love John Cusack (The Grifters being my favourite), but can’t stand “High Fidelity”.
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Thank you, again, my friend. THE GRIFTERS is a gem of a film. I have since seen and enjoyed IDENTITY and 1408 – twice each.
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I like 1408 as well! So good to read your blog once again.
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So glad to have you reading again! 🙂
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Happy to be back reading! You always give mevfood for thought.
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I do my best, thank you.
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