Wide Angle

The Holy Trinity of John Cusack Movies Tells a Cautionary Tale

Rewatching Say Anything, Grosse Pointe Blank, and High Fidelity made me glad this trilogy is over.

John Cusack in Say Anything, Grosse Pointe Blank, and High Fidelity.
Photo illustration by Slate. Photos by Twentieth Century Fox, Buena Vista Pictures Distribution, and Touchstone Pictures.

The first time we see Rob, John Cusack’s record-collecting romantic in High Fidelity, he’s on the verge of screaming. His long-term girlfriend, Laura, is walking out on him, and Rob, who resents not only her departure but the way it interrupted the song he was listening to, runs to the window as she gets into her car. “If you really wanted to mess me up,” he yells down at her, “you should’ve got to me earlier!”

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The sight of a bereft Cusack shouting from a second-story window acts as a warped reflection of what remains the most iconic image of his career: Lloyd Dobler standing outside his ex-girlfriend’s window, serenading her with a portable stereo hoisted over his head. The story from the making of Say Anything is that Cusack wanted the music blaring from Lloyd’s boombox to be by the ska-metal band Fishbone but writer-director Cameron Crowe argued, correctly, that something that aggressive would make Lloyd seem like a deranged stalker rather than a pleading lover. That’s the energy that pours out of Rob’s window as he cranks up the 13th Floor Elevators’ “You’re Gonna Miss Me” and screams across a city street. He’s not trying to win his girlfriend back. He’s shoving her away so he can get back to the familiar business of being bitter and alone.

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High Fidelity, which was released in 2000, doesn’t just reflect back on Cusack’s breakthrough movie. It functions as the close of an unofficial trilogy that begins in 1989 with Say Anything and continues through 1997’s Grosse Pointe Blank. In all three, Cusack plays a man who’s trying to figure out his life, not just who he is but what he stands for, and the later in life the story catches up with him, the more dire his situation becomes. Say Anything’s Lloyd Dobler is a high school senior struggling to figure out his next steps. Grosse Pointe Blank’s Martin Blank is a professional hit man thrown into a crisis of conscience by his imminent 10-year high school reunion. Rob Gordon is an aging hipster who realizes that leading the life of a “professional appreciator” has left him with few achievements of his own. It’s too much to say that he’s playing the same character in all three (although Martin Blank is definitely a Sliding Doors version of Lloyd Dobler), but there’s enough connecting them to make them feel like overlapping parts of a whole, a Venn diagram that verges on a single circle.

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As a white child of the suburbs who grew up along with, if several years behind, Cusack, I both identified with these characters and aspired to be them. Lloyd became a touchstone for a generation of straight men and the people who pined for them: a wise-beyond-his-years teenager who was both vulnerable and strong, guileless and worldly. I wasn’t killing people for money in my mid-20s, but I was, like a lot of Gen Xers, dreading the prospect of a world in which career stability came at the price of my soul. But by the time of High Fidelity, the relationship had soured. When I read the Nick Hornby novel from which it’s adapted the year I graduated from college, I saw its glib quirkiness and pat moralizing, but I also felt like it was describing a type of person I’d never seen depicted before, a person I knew and sometimes was. But I couldn’t see myself in Cusack’s Rob, and it wasn’t until rewatching the film recently that I realized why.

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We remember High Fidelity as a movie about pop-cultural obsessives, about dudes trading Top Five lists and Jack Black chasing a customer out of the store for asking about the wrong record. But what struck me watching the movie now, 20 years later, is how angry Rob is. He’s in a fury from the movie’s opening minutes, when Laura grabs his attention by ripping his headphone cord out of the stereo. He’s like a newborn who’s been ripped from the womb and does not like the world he’s been thrust into. Her eyes are red, her pale skin blotchy, so it’s clear they’re already in the middle of a fight. But Rob just wants to be alone with his records, an endless collection of songs about men and the women who did them wrong.

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For Rob, music is both a comfort and a curse. It salves his heartbreak, but it also intensifies it and sets terms no real-world romance can match. (“Did I listen to pop music because I was miserable?” he asks, “Or was I miserable because I listened to pop music?”) In the course of High Fidelity, he tracks down the women on the other end of his “desert-island, all-time, top five most memorable breakups,” beginning, most painfully, with the girl who broke his heart in middle school. But he discovers that their relationship, which amounted to a few days of after-school necking, meant so little to her that it didn’t even count. It’s only in the echo chamber of Rob’s head that it’s grown into a monster, the explanation and the rationale for his subsequent misanthropy.

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Watching the Cusack trilogy in close succession, you can chart the steady extinguishing of hope, the journey from youthful idealism to embittered resignation. Lloyd is almost painfully open to the world. Words spill out of his mouth as fast as he can think them, and when he’s talking about dating Diane Court (Ione Skye), the class valedictorian with “the body of a game-show hostess,” his shoulders jiggle with nervous anticipation. (Later, after the first time they have sex, his whole body quivers, as if he’s both awed by and a little afraid of what’s just happened.) Crowe has said that the character embodied “optimism as a revolutionary act,” the idea that you could know that the world is a dangerous and terrible place and choose to live as if it weren’t, because hardening yourself is worse than wearing your heart on your sleeve. (When a friend warns him that pining for the most popular girl in school will only wind up with him getting hurt, Lloyd responds, “I want to get hurt!”) He’s an existential hero in teen-romance clothing, unable to be anything other than what he is. When a male classmate, incredulous that Lloyd has snared a date with the school’s most coveted girl, asks him, “Who are you?” he responds, “I’m Lloyd Dobler.”

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Martin Blank is who Lloyd might have become if he’d never worked up the courage to ask out Diane Court but did keep up his intensive kickboxing regimen. Instead of embracing the unknowable future the way Lloyd did, Martin ran from it, leaving his high school sweetheart, Debi (Minnie Driver), stranded on prom night and disappearing without a trace. When he comes back 10 years later, it’s as a killer for hire, a former government contractor who’s gone out on his own in part because he likes the solitary lifestyle. The movie’s underlying gag is that while Martin is a professional assassin, he doesn’t think that necessarily makes him a bad guy. Most of his victims probably deserve what they get, and anyway, if he didn’t kill them, somebody else would. “It’s not me,” he tells one, right before he pulls the trigger. Martin is fully alienated from his labor, but no more so than the classmate who went into real estate and sold Martin’s childhood home to a company that knocked it down and replaced it with a convenience store. “You can never go home again,” he muses, “but I guess you can shop there.”

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Where Lloyd embraced the future, Martin is terrified of it, so much so that his life has frozen in place. The movie’s soundtrack (which would fall in my own personal top five) is full of great songs, but they’re almost all drawn from the previous decade, and when Martin visits Debi, who has been married and recently divorced, at home, it’s in her childhood bedroom, which has remained virtually untouched. It’s a second-chance movie, one that, by the end, effectively allows Martin a do-over on the past 10 years of his life, but for all that he’s been through, in some ways he’s never left.

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For Rob, who’s in his mid-30s, the future is a dead end. He’s seen it, and he wants no part of it. The movie binds us at first to Rob’s self-pitying account of his and Laura’s breakup, but we eventually find out that he cheated on her and then berated her for having an abortion. Lloyd takes his lumps, and Debi calls Martin “broken” (later amending it to “mildly sprained”), but Rob is bent. His inability to progress through life isn’t a result of youthful naïveté or quarter-life fumbling; it’s because, on some level, he doesn’t want to, and he won’t let anyone make him. He sneers at Laura for taking a job at a law firm and losing the pink dye from her hair, because he only sees her moving forward as moving away from him. (Lloyd didn’t know where he wanted to go, but at least he knew he wanted to be with Diane.)

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There’s a seething quality to Cusack’s performance in High Fidelity that seems intentional, although the movie doesn’t always know what to do with it. Being lost and directionless is part of Lloyd and Martin’s charm, but by Rob’s age, it’s no longer so endearing. The tour through Rob’s past breakups starts off as a comedy of errors, the equivalent of getting to the point where you look back on your old relationships and no longer wonder why you broke up but why you were ever together. But there’s one that underlines how cruel Rob’s haughty diffidence can be. When he catches up with his ex-girlfriend Sarah (Lili Taylor), it’s clear she’s in a worse place than he is, and she doesn’t try to hide her deep depression. But rather than reaching out to another soul in distress, Rob is repelled by her; he’s supposed to be figuring out his own problems, not dealing with someone else’s. Rob walks her to her apartment, and the way she lingers in the doorway makes it clear she wants, even needs, him to come in. But he turns and walks away, and we see her recede over his shoulder, still waiting for him to see her. It’s the most painful moment in the movie—and the one that makes Rob seem like the biggest asshole.

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In retrospect, it’s not surprising that Cusack left this character type behind after High Fidelity, or that he’s never seemed as right for any role as he did those three. (On the occasion of Say Anything’s 20th anniversary, John Mahoney, who plays Diane’s father, called it the movie where he “found his Cusackness.”) They’re all stories about growing up, and about realizing that it’s not something you just do once and get it over with. Part of that growth is putting the past behind you, and part of it is accepting that, 20 years later, it’s time for someone else to tell that story instead.

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