Lloyd Dobler is Cameron Crowe’s original manic pixie dream date

The image of John Cusack’s Lloyd Dobler earnestly, defiantly holding a boombox above his head has become such an indelible part of pop culture that it’s easy to forget that Lloyd is not, in fact, the protagonist of Say Anything. He has the screen time of a co-lead, but in the way the narrative frames him, he’s “the love interest”—the less developed character whose life and actions almost exclusively revolve around the more complex, three-dimensional object of his affections, in this case, beautiful valedictorian Diane Court (Ione Skye). Thanks to the quirky female leads who populate his later films, writer-director Cameron Crowe would go on to inspire the naming of the famed (and admittedly complicated) “Manic Pixie Dream Girl” archetype. So it’s fascinating that for his directorial debut, Crowe actually presented a gender-flipped version of that dynamic—one that’s as refreshing today as it was when the film premiered 30 years ago this month.

Released in 1989 and set during the anxious summer after high school, Say Anything (or Say Anything… to use the official styling) feels like a graduation for the 1980s teen-movie genre. Crowe had helped kick off the trend in the first place by penning the screenplay for Amy Heckerling’s 1982 sleeper hit Fast Times At Ridgemont High, which was based on his own experience going undercover as a high school student. In Say Anything, however, Crowe is much less focused on the rigid cliques and archetypes that dominated Fast Times and John Hughes’ generation-defining teen films of the era.

Diane is a shy, bookish “brain,” but she’s also got droves of suitors regularly calling up her house. Her social isolation is largely self-inflicted; she’s intensely focused on academics and seemingly plagued by a lot of anxiety as well. She’s also just got a lot on her plate—a job at a nursing home, an impending British fellowship, a close Gilmore Girls–esque relationship with her loving single dad, Jim (John Mahoney), and, of course, her burgeoning relationship with Lloyd. Diane’s main stress is time management, which is an acutely observed roadblock for a type-A teenager.

Lloyd, meanwhile, is a much more static character, at least from a narrative point of view; his sole drive throughout the film is courting Diane. That doesn’t mean he’s not a dynamic screen presence, however. As written by Crowe and endearingly embodied by Cusack, Lloyd is a fascinating collection of contradictions: nerdy and athletic, vulnerable and brave, aimless and responsible. He’s awkward around adults, but a natural caretaker among his peers. Unlike the driven Diane, Lloyd doesn’t have any professional or academic goals for his post-high school life. What he comes to realize is that maybe the thing he’s best at is just being there for Diane.

The closet parallel for Lloyd Dobler is 30 Rock’s Criss Chros (James Marsden), the hapless but earnest doofus who turned out to be the perfect partner for Liz Lemon, precisely because his lack of drive is the perfect balance for her boundless ambition. In 30 Rock, it’s an idea that’s at least partially played as a joke. In Say Anything, it’s played entirely earnestly. The movie finds nobility in Lloyd’s dedication to being a support system for his more ambitious partner, which is a message that’s often aimed at women and very seldom aimed at men.

Like a lot of Cameron Crowe movies, Say Anything is full of beautifully realistic, intimately observed interactions that unfold against a plot that’s far weirder and more hyper-specific than you’d expect it to be. Put it this way: You don’t watch the first 40 minutes of Say Anything’s amiable teen romance and think, “Oh, this is obviously going to become a movie about tax fraud in elder care.” But that’s what happens when Jim is informed that he’s been put under investigation by the IRS. As Diane’s relationship with Lloyd grows more intense and the weeks until she leaves for her fellowship tick by, she has to figure out what she wants to prioritize in her life, and how much she can trust her dad’s pledge that they’ll always be open and honest—that they can truly “say anything” to each other.

Say Anything is ultimately a movie about co-dependency, which the film is curiously neutral about. There’s definitely something slightly creepy in the way that Diane keeps bouncing back and forth between these two men who entirely dominate her world. (That she has no other real friends is a central component of her character.) But Say Anything works because it has so much empathy for all three of its lead characters. As Roger Ebert observed in his glowing review of the film, Say Anything is a movie about morality that isn’t trying to impart a didactic lesson or message. Mahoney’s Jim is one of the most complex parents ever depicted in a teen rom-com. He’s at once loving and possessive, selfless and delusional, corrupt and caring. It’s something Crowe writes well and Mahoney plays even better.

In addition to the openhearted empathy Crowe brings to his best films (and which crosses over into twee sentimentality in his worst ones), Crowe’s greatest skill as a filmmaker is his ability to create iconic moments. Jerry Maguire is absolutely brimming with them, and so is Say Anything—from Lloyd’s “I gave her my heart and she gave me a pen” to his rambling monologue about how he doesn’t want to sell anything, buy anything, or process anything. The boombox scene is the ultimate example of Crowe’s eye for iconography. Say Anything didn’t make much of a splash at the box office when it was released, but its cultural longevity is clear. The image of someone holding a boombox above their head means something, beyond just being a nod to the film. It’s become shared cultural shorthand for longing, persistence, redemption, and romance. (It’s also worth pointing out that Lloyd’s big romantic gesture doesn’t work. It’s not the dulcet tones of Peter Gabriel that bring Diane back to Lloyd; it’s her realization that he offers the honesty and open communication she wants in a relationship.)

The boombox scene was the last thing shot on the last day of filming, and Cusack was originally reluctant to do it, fearing it made Lloyd look too subservient. Crowe and Cusack settled on the scene being defiant as much as it is lovelorn, some of which might just have stemmed from Cusack’s own defiance at having to film it. After searching for the right song (they played Fishbone’s “Turn The Other Way” on set, but originally planned to use Billy Idol’s “To Be A Lover”), Crowe found the perfect fit in Peter Gabriel’s “In Your Eyes.” Gabriel initially turned down the request, telling Crowe, “Well, when he takes the overdose it just didn’t feel like the right kind of use of the song.” It turned out he’d accidentally watched the John Belushi biopic Wired, whose producers had also requested to use the song.

James L. Brooks—who mentored Crowe and produced the film—helped convince 20th Century Fox to shell out some big bucks for the rights to the song. Say Anything was actually the brainchild of the legendary film and TV creator, who saw something he liked in Crowe’s screenplay for the largely forgotten teen comedy The Wild Life and decided to take him under his wing. (He’d later do the same for a young Wes Anderson.) Brooks hired Crowe to develop a story about the close relationship between a teenage girl and her criminal father. Crowe created the Lloyd character himself, inspired by an earnest young neighbor who loved kickboxing. Lawrence Kasdan was originally supposed to direct, but it was eventually decided that Crowe—who had never directed a film before—should helm the project himself.

It’s worth acknowledging that Crowe’s directorial career was shaped by the kind of mentorship and risk-taking that isn’t as regularly offered to people who aren’t white men. (That’s also true of his early career as a teenage rock critic, detailed in his semi-autobiographical passion project Almost Famous.) In a 2002 Entertainment Weekly interview, Crowe himself makes fun of how green he was on set, not even realizing that he had to shoot close-ups in addition to wide shots. Nevertheless, he was given a $16 million budget for his debut feature. Amy Heckerling made Fast Times on a $5 million budget. Thirteen years and several box office hits later, she struggled to find a studio to get Clueless off the ground for $12 million.

To Crowe’s credit, his debut feature is about the inner emotional life of a teenage girl, and he makes time for a funny, pointed critique of teenage toxic masculinity, too. In the throes of depression after Diane breaks up with him, Lloyd briefly seeks solace in the angry teenage boys who hang out behind the Gas ’n Sip. “That was a mistake,” he deadpans, when their advice boils down to “Bitches, man!” In choosing to portray Lloyd as the kind of guy who almost exclusively hangs out with women (a more interesting choice than the overused rom-com dynamic wherein the male lead has one really close female best friend), Crowe populates his film with a bunch of memorable supporting turns from women. Joan Cusack is great as Lloyd’s frazzled older sister, Constance. Lili Taylor is even better as his angsty, guitar-playing friend Corey—someone who deeply loves Lloyd but who isn’t in love with him.

Like 10 Things I Hate About You, Say Anything is hugely respectful toward the teenage characters at its center, even as it maintains just enough ironic detachment to laugh at their myopic tendencies. And it’s all the more romantic for being a movie that’s not about love-at-first-sight or contrived romantic shenanigans. To get Diane to go out with him, Lloyd simply calls her up and asks her out. She takes him up on the offer because he makes her laugh. There’s not one single turning point in Diane and Lloyd’s tentative “friends with potential” relationship but a bunch of little ones—the two of them checking up on each other from across a crowded graduation party, Lloyd sweeping away broken glass in Diane’s path, the incredible sweetness of the first time they have sex. As NPR’s Linda Holmes put it, “The Hughes fantasy that someone unattainable—rich, popular, beautiful, athletic, rebellious—might notice you is replaced with a different ideal: that a very, very good person might fall in love with you.”

The final shot of Say Anything is an homage to The Graduate, but one that finds hope where that movie found fear. The tricky thing about teen rom-coms is that you’re often left with a nagging feeling that a couple that met in high school probably isn’t going to work out long-term. In the specificity of Lloyd and Diane’s yin-and-yang dynamic, Crowe creates a teenage duo that feels like they actually might.

Next time: We try to figure out why He’s Just Not That Into You.