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John Cusack Was Once King of the Romantic Comedy Because He Was All Wrong for the Role

The star of ‘Say Anything’ and ‘High Fidelity’ epitomized Generation X’s disdain for mainstream acceptance. But his subsequent career has illustrated the challenges of sustaining a no-sellout ethos.

Welcome to Misleading Men, a regular feature where we look back at the actors who ruled Hollywood for one brief shining moment.

It happened — I was there, I saw it — but in hindsight, it seems strange that John Cusack was once considered a heartthrob. That’s no knock on his looks — even at 54, he’s boyishly handsome — but more a comment on who we normally think of as a Hollywood leading man. Picture the actors who have been the stars of romantic comedies. Hunks like Matthew McConaughey. Nice guys like Tom Hanks. Puppy dogs like Billy Crystal. Off and on over a couple decades, Cusack was in rom-coms, but he often seemed like he saw through the genre — as if he was cluing us into the fact that we all knew there was something fraudulent about them. Even when his characters were cuties, there was something a little removed about how Cusack approached the roles — like he wasn’t willing to fully commit. 

Normally, this wouldn’t be the type of guy you’d want to star in a love story. Lots of Hollywood films are fantasies, but romantic comedies in particular are geared to audiences who just want to believe. Cusack was never that gullible. There has always been something appealingly Gen X about him — a principled reluctance to buy into the system, even if that system was simply the idea that love conquers all. He represents an era when “selling out” was considered the most unforgivable sin. But watching his rom-coms now, they tell a story about how his generation had to learn such idealism was going to be hard to sustain.

Cusack started landing film roles in the early 1980s, and his first big break was in The Sure Thing, a smart romantic comedy about young people during a time when movies like that were at a premium. (For every John Hughes — whose Sixteen Candles Cusack had been in — there were a few Porky’s or Revenge of the Nerds.) Cusack was a teenager when he played Walter, an incoming college freshman looking for an easy lay who ends up falling in love with the brainy, beautiful Alison (Daphne Zuniga). The teen magazines took notice of him, and his director Rob Reiner told the Chicago Tribune, “He’s attractive in an offbeat way, he’s sexy, and he can play comedy, which is a very rare combination.” But all the attention didn’t seem to phase Cusack, who came across as more serious and mature than the Brat Pack crowd. “It’s ridiculous when you think of it,” he said in that Tribune profile. “I went to this big industry screening for The Sure Thing in Los Angeles, and I was being asked these dumb questions for a television interview, and it was all just silly.” The kid seemed like he had some depth to him.

That same year, he did Better Off Dead, which you have probably not heard of unless you’re a member of Generation X. In this surly teen comedy, he plays Lane, the prototypical outsider 1980s youth who’s dumped by his girlfriend — she starts dating a jock — and is disillusioned by the world around him. (Even when he tries to kill himself — which is presented in a lighthearted way — it goes badly.) While Hughes’ movies portrayed teenage life as basically endearing and wholesome, Better Off Dead (which wasn’t a hit) evinced a wised-up, sarcastic attitude, with Cusack viewing life as one big scam. Years later, he would talk about the fact that his sensibility was forged by “coming of age during the Reagan administration, which everybody has painted as some glorious time in America, but I remember as being a very, very dark time. There was apocalypse in the air; the punk rock movement made sense.” Even though Lane ultimately gets the cool French foreign-exchange student (Diane Franklin), there was an antiauthoritarian vibe to the film — and to Cusack.

He made other movies, but his next big love story was the one that cemented his heartthrob status. Say Anything isn’t a traditional rom-com — it’s more of a serious coming-of-age comedy mixed with a teen love drama — but it was a refreshingly grownup look at adolescent uncertainty. It was about Lloyd Dobler (Cusack), a regular dude who’s really into kickboxing, and Diane (Ione Skye), the class overachiever who could have been the embodiment of the screenwriting cliché of the female love interest who doesn’t know how beautiful she is. But writer-director Cameron Crowe invested the film with real feeling — these people were nuanced, sensitive individuals — although Cusack wasn’t sure at first that Lloyd was layered enough.

“I thought that the character didn’t have enough dimension,” he said in 2019, later adding, “I was listening to the Clash, so I wanted him to have thoughts outside of his high school, or county, or state; to think about the world the way people do when they’re young.” 

If that sounds pretentious, well, there’s something inherently young about that worldview — that belief that the things you’re into are very important and could change the world, man. It’s also very Gen X, and Lloyd became a poster boy for its defiant anti-compromise attitude. His famous “I don’t want to sell anything” spiel is entirely a product of not wanting to become a corporate drone. Even when he holds up that boombox outside of Diane’s bedroom window — the movie’s most romantic moment — he’s wearing a Clash shirt, the proud nonconformist to the end. For both the actor and the character, integrity mattered. Say Anything builds to the realization that Diane’s father (John Mahoney), who disapproved of her dating Lloyd, is, in fact, a crook — the film’s indication that Lloyd is actually the better, nobler man. The older generation had sacrificed their scruples for the sake of money and comfort — Lloyd would stay true to himself. No wonder so many women my age adored Lloyd.

That importance placed on personal integrity extended to how Cusack felt about Say Anything. In that same 2019 interview, he went out of his way to argue that it wasn’t a “teen movie”: “[T]his was much more just a film. It’s a good piece of writing and then it was a real good collaboration between me and Cameron on my character. It was a really well-cast, well-shot movie. … People were trying to think of it as just a film, they weren’t thinking of it as a teen film or a genre film.” It might seem like a meaningless distinction — a “film” versus a “teen movie” — but it speaks to Cusack’s keeping-it-real ethos. In a decade in which authenticity was prized — where college-rock bands like R.E.M. and the Replacements were celebrated for cultivating their own sound and spitting in the eye of corporate radio — Say Anything felt refreshingly real in a way other teen movies didn’t. 

Cusack didn’t make another Gen X touchstone until 1997’s Grosse Pointe Blank, a dark comedy about a hitman who’s at a personal crossroads and decides to go to his high school reunion to reconnect with his past. Inspired by Cusack’s own high school reunion, the movie (which Cusack also co-wrote) was a very 1990s, post-Pulp Fiction endeavor, cleverly dancing between genres and sporting an anarchic spirit. But at the same time, Grosse Pointe Blank revelled in the nostalgia of bygone acts like English Beat, Violent Femmes and, yup, the Clash, who all peppered the soundtrack. If Cusack’s previous movies were about being young, Grosse Pointe Blank wryly observed that those 1980s kids were now no longer kids — without warning, they’d become adults having to navigate the grownup world they used to sneer at. 

A quirky movie that didn’t have a big budget but wound up turning a modest profit, the idiosyncratic Grosse Pointe Blank is an endangered species in today’s Hollywood — a fact Cusack likes to point out. “We were lucky at that time there was still a connection to the 1960s and 1970s [Hollywood system],” he said a couple years ago at a revival screening. “Now studios test-market movies. They treat art like it’s a science program. You can’t do that.” In Grosse Pointe Blank, his character courts his old love Debi (Minnie Driver), and Cusack proved he’d lost none of his sly charm. But where other rom-com men try to be adorable, his characters wanted you to know that they were smart — and it’s a testament to Cusack’s choice of material that his leading ladies are smart, too. (Debi, like the love interests in The Sure Thing and Say Anything, is the furthest thing from a sunny, klutzy ditz.) 

Grosse Pointe Blank was a passion project, and so was 2000’s High Fidelity, his adaptation of the Nick Hornby novel and transplanted from London to Cusack’s beloved Chicago. High Fidelity (which Cusack co-wrote) is a quintessential Gen-X film in the same way that Say Anything is: In the latter, the teen Cusack character is jaded but still fairly innocent, whereas High Fidelity’s Rob is a dude in his 30s whose devotion to music and pop-culture arcana is starting to feel like a crutch. The movie was a succinct summation of all the things that a certain kind of arrested-adolescent bro loved — list-making, pointless debating, moaning about how girls don’t “get” you, thinking that your self-absorption made you deep — and lamented whether guys like Rob could ever actually grow up. 

It was fascinating to see Cusack in the role: As a younger actor, he projected a vibrant maturity that, as Rob, had calcified into a bitter contempt for the dead end he’d made of his life. (Anybody in his teens would think owning a record store would be the coolest job in the world — High Fidelity disabuses you of that notion.) As Rob reaches out to his exes, trying to figure out what went wrong in his love life, Cusack lets you see how pathetic the guy is — and, at the same time, makes you sense his capacity to change. And like with Grosse Pointe Blank, the film seemed to be a commentary on the conventions endemic to Hollywood love stories. There’s a happy ending in High Fidelity, but not before the not-entirely-endearing Rob takes stock of the manchild he’s been. That transformation was especially poignant coming from a Gen Xer like Cusack, who’s so concerned about not betraying his principles, because he’s playing a guy who doesn’t realize he’s stuck in his ways and has to bend a little to fully commit to a healthy, loving relationship.

Also like Grosse Pointe Blank, this was the sort of left-of-center movie that, although a moderate hit, you’d have a tough time financing today. “The idea of trying to get that movie made now, from a big studio, I just don’t think it’d happen,” he said in 2019. “We were getting away with it for different reasons, but mainly we didn’t have to sanitize it. It was a different era in the film business.” 

Both films felt like major-label albums from former indie-rock bands — like when Sonic Youth was suddenly signed to Geffen, or R.E.M. jumped to Warner Bros. — in which the artist hadn’t sacrificed a thing to get a larger platform. Like those albums, Grosse Pointe Blank and High Fidelity suggested a way for a Clash-loving guy to avoid “selling out” while still making art that mattered to him. And when he did occasionally give in to the man — say, by appearing in a big, dumb action movie such as Con Air — he tried to hold onto his dignity. “You can subvert commercial movies in interesting ways,” Cusack once said. “In Con Air, I put in the Dostoyevsky quote, ‘The degree of civilization in a society can be judged by observing its prisoners.’ That wasn’t in the script. Or I thought, ‘All right, I’m going to wear inappropriate footgear. I’ll be the first post-Charlton Heston non-biblical action star to wear sandals.’ I would do ridiculous things.”

This was a period in which he was doing daring work — especially The Thin Red Line and Being John Malkovich — but eventually, unfortunately, he did decide to try his hand at more mainstream rom-coms. It’s possible not a single soul has thought about America’s Sweethearts and Serendipity in the 20 years since they came out. And what of Must Love Dogs, which I swear is not a title I made up? These bland misfires didn’t seem to engage Cusack, and although they were commercially successful, he wasn’t keen on repeating them.

“That’s not really my genre or the kind of thing that I like,” he told the New York Times last fall when talking about romantic comedies, later adding, “Must Love Dogs was the best thing I could get at the time. It wasn’t something that I would be looking to do. When somebody is trying to force you to do something that is easily understood, you’re always trying to get to something that’s more dangerous emotionally.” In the interview, he came across, as he had as a teenager, as a guy who was suspicious of the system, still wanting to give the finger to mainstream acceptance. “Especially if it’s a genre piece, you try to make them the best versions of that,” he said. “I don’t know what people thought they wanted me to do. I never could understand that. They want you to be a straight leading man, but your instinct is to do weirder stuff.”

By and large, “weirder stuff” has been the path he’s chosen this century. He’ll do the occasional blockbuster, like 2012, or irreverent comedy, like Hot Tub Time Machine. And he can remind people what a fine dramatic actor he is in something like Love & Mercy. But too often, he’s drifted toward VOD junk. (Have you seen Singularity, Arsenal or Blood Money? Well, he made all three in 2017.) “Sometimes you do movies for money, sometimes you do them for art, and sometimes you do movies for money to pay for the movies you do for art,” Cusack said in 2018. “It depends on what you’re offered and what you’re going to do and all that.” He was even blunter about his dilemma in last year’s Times profile: “You try to do — it’s a cliché — one for them, one for you. Then it becomes four for them, one for you. Then it becomes all for them, none for you.” 

This is the cruel reality of Hollywood, but from someone who for so long seemed above commercial compromise, the recent paycheck gigs have been dispiriting. Every time I hear his comforting voice in Chevy ads, it makes me a little sad. I’m sure it’s a lucrative gig, but what would Lloyd think?

Not that I judge Cusack too harshly about this. The whole notion of “selling out” was very Gen X, but the world changes and artists have to adjust. All of us who swore we’d never trade away our souls have discovered that life isn’t so simple. What’s interesting about Cusack as a former romantic leading man was how he embodied that stick-to-your-principles mindset — and then demonstrated how hard it is to hold onto as you get older. In Cusack’s love stories, he tried to challenge the status quo, assuming that audiences were smarter than the trite teen films and rom-coms they were being served. That’s why his movies still feel daring and alive — they’re not playing by the rules, liberated by what they’re getting away with. When you watch other stars’ romantic comedies, you see the comforting familiarity of formula. Cusack was a pinup who thought those niceties were a crock. 

When Fall Out Boy were starting out in the early aughts, they had a thrash-y pop-punk song called “Honorable Mention,” in which they declared to their beloved, “I can be your John Cusack.” It’s the perfect embodiment of teenage devotion, appropriating the boyish, defiant idealism that defined Lloyd Dobler. But I also think of Cusack’s heroes the Clash and one of their best songs, a cover of “I Fought the Law,” which repeats over and over, “I fought the law / And the law won / I fought the law / And the law won.” 

Maybe that’s what ultimately separates Cusack from his fellow romantic leading men. There was something about his characters that made you know they weren’t supposed to be the winners — but they were going to go down swinging anyway. They were the outsiders Hollywood studios don’t make rom-coms about. But he made sure, for a brief time, that they did.