NOTE: Though I take great pains in most of my reviews to avoid revealing plot details, I do include them in some of my longer “100 Favorite Movies” essays. Significant spoilers ahead!

For kids like me who came of age in the 1980s, Say Anything... was a big deal. In 1989, when the film was released, I was just about to graduate high school—exactly like the two protagonists, Lloyd Dobler (John Cusack) and Diane Court (Ione Skye). Lloyd in particular, was different from any of the movie teenagers we’d seen up to that point in the decade. He wasn’t a popular kid, but he wasn’t a nerd, and his peers clearly respected him. He was an underachiever but not a slacker or a stoner; an athlete but not a jock. And although he dressed like a rebel, his teachers viewed him as a responsible young man. This combination was irresistible to any high schooler who felt even a little bit like an outsider (which is pretty much all high schoolers). Practically everyone in my generation wanted to either be or to date Lloyd Dobler. And that, I think, is the reason that this modest film became a classic teenage coming-of-age picture, a standout even in an era notable for its many memorable entries in that genre. But Say Anything’s reputation has deteriorated somewhat in the years leading up to its 30th anniversary. There are some valid reasons why millennials might view this beloved Gen-X touchstone as an overrated relic from a decade littered with misogynist cinema. But regardless of whether you love this film or thoroughly dislike it, it’s a different movie than many seem to remember it. Similarly, whether you perceive Lloyd Dobler as the most romantic heartthrob in ‘80s teen cinema or as an example of the problematic male role models of its time, it’s worth reexamining what’s different and special about him and the film.

Lloyd’s iconic status is partly due to the artistic tension between his two creators.  Writer/director Cameron Crowe has a tendency to write soft characters who are often too nice to be interesting, while Cusack is always trying to shed the lovable guy-next-door image he’s had since his early leading roles, in films like The Sure Thing, Better Off Dead, and One Crazy Summer. He’s still pursuing this effort well into his fifties, but his more sinister, morally ambiguous characters never quite fit his screen persona as perfectly as these earlier roles. But in the case of Lloyd, Cusack’s darker acting choices provided a much-needed counterweight to Crowe’s sweetie-pie instincts. Lloyd’s a lovable guy-next-door but he’s got some edge.   
On the surface, Say Anything is a typical opposites-attract rom-com—much like the movie that provided Cusack with his first starring role, Rob Reiner’s The Sure Thing (1985). But that terrific film, and so many others like it, follow a familiar and reliable narrative formula: two mismatched people meet and dislike each other, only to spend the rest of the movie slowly, and unwittingly, falling in love. Say Anything isn't built from that mold in the slightest. Lloyd is an honorable but otherwise unspectacular high school grad who pursues and falls for the beautiful and brilliant class valedictorian. Diane, for her part, is instantly charmed by Lloyd, but she sees him as a summer fling: a fun companion for her last months at home before moving to England, where she’ll begin an academic fellowship.

The central conflict in Say Anything requires far less narrative contrivance than the typical rom-com plot, and ends up feeling closer to the real-life experience of falling in love for the first time: the emotions are much more intense for one half of the couple than the other. The hopelessly optimistic Lloyd falls for Diane, and falls hard. Diane, who’s more pragmatic, really likes him, but isn't sure her feelings go beyond that, and her insecurity about her future makes her wary of forming a deep connection with Lloyd or any potential suitor. There’s an imbalance, and it plays out in ways that are funny, and poignant, and sometimes both. Lloyd is overwhelmed when they have sex for the first time, and while the movie doesn’t come right out and say it, we get the sense that he may not have done this before.  Diane, for her part, seems more experienced and sanguine. She encourages Lloyd to relax and to listen to the song playing on the radio (Peter Gabriel’s "In Your Eyes,"). The scene is the inverse of the sequence Crowe wrote for Jennifer Jason Leigh’s character in Fast Times at Ridgemont High (1982). Both scenes resonate because of the authentic, unexaggerated ways they present the characters’ emotions and physicality. But the Fast Times scene depicts an unpleasant sexual initiation, in which Leigh’s fifteen-year-old Stacy Hamilton loses her virginity to a much older man who is clearly taking advantage of her. Lloyd’s first time, by contrast, is with a gentle and sensitive peer. She may not feel as strongly for him as he does for her, but there's no question that they care deeply about each other. I lost my own virginity about a year after seeing this picture, with a lover very much like Diane Court in many respects—everyone should be so lucky to get so lucky.
The gender dynamics of Say Anything, where the female lead is more accomplished and emotionally centered and the male lead more vulnerable, is another element that sets this film apart from most of its contemporaries. The movie is usually remembered as Lloyd’s story, for many reasons: It's apparent from the picture's overall vibe, its fashion sense, and the hard rock songs on the soundtrack that Lloyd is the character writer/director Crowe most identifies with. The top-billed Cusack was also a bigger star than Skye, and few would dispute that he’s also the better actor—one of the best of his generation. But actually, the screen time is shared equally between the two leads, and it’s Diane’s narrative arc that drives the story.

The daughter of folk singer-songwriter Donovan and model Enid Karl, Skye had made her film debut three years earlier in Tim Hunter’s masterful thriller River's Edge (1986). Though Diane is nothing like her character Clarissa in River's Edge, Skye’s role in Hunter’s distinctly adult-themed teen movie lends her Say Anything character some onscreen gravitas in the same way that Cusack's well-established persona made it feel like we had been hanging out with him for years before this movie. Like Lloyd, Diane is somewhat of an outsider. Since she’s smart, beautiful, and shy, many of her peers view her as aloof and maybe a bit stuck-up, though she’s anything but. Her best friend is her father, a single dad who’s affirming and supportive to a fault, played by the great character actor John Mahoney (Tin Men, Moonstruck, and TV’s Frasier) in one of the most indelible performances of his long career.
It’s easy to see that Diane is way out of Lloyd’s league, but also why she’d be attracted to him. He represents a release from her life of high achievement. On their first date, Diane admits she’s never gone out with someone as “basic” as him, a comment Lloyd tries valiantly to construe as the compliment she intended. Lloyd makes Diane feel safe. She shares with him her insecurities and doubts, in ways she hasn’t been able to do with anyone else. For his part, Lloyd sees the real her, not the idealized version her father and her classmates perceive. 

Lloyd is an atypical ‘80s teenager and teenage guy specifically. He lives with his sister, a single mother played by Cusack’s real-life sister Joan, and his closest friends are all women—played by the winning trio of Lili Taylor (Mystic Pizza, Dogfight, I Shot Andy Warhol), Pamela Segall (who would become Pamela Adlon, star and producer of the aclained TV shows Louie and Better Things), and Amy Brooks (daughter of James L. Brooks, Say Anything’s executive producer). Lloyd is the opposite of ambitious. When asked by Diane’s father about his plans for the future, Lloyd instead talks about all the things he DOESN’T want to do. All he knows for sure is that he wants to spend as much time as possible with Diane. Lloyd is unintimidated by his girlfriend’s success and would be more than happy playing a supporting, and supportive, role to a bright, motivated woman who may be destined for great things.

When Diane eventually decides it’s best for her and Lloyd not to get too attached and abruptly ends their relationship, Lloyd is shattered. He searches his soul for answers and seeks the counsel of his close friends, not to mention a bunch of bros hanging around the local Gas-N-Sip. But he can’t understand what happened. Though Diane doesn’t ghost him, she cuts things off without much explanation and won’t engage when he begs for one. This may be because Diane is unable to articulate her feelings even to herself. She loves Lloyd too, but the seriousness of their relationship adds to her generalized stress and confusion, her uncertainty about the future, her anxiety about leaving home, and her relationship with her father, which grows more complicated over the course of the film when the IRS accuses him of fraud and begins a criminal investigation of his business.

Lloyd and Diane’s longing for each other leads to one of the most iconic moments in the last thirty years of American cinema, in which he stands outside her bedroom window, holding a boombox above his head that’s playing, of course, “In Your Eyes”. But while the scene is undeniably legendary, Lloyd’s efforts to win Diane back play differently with members of different generations. 

To Gen X’ers like me, the image of a vulnerable Cusack with his heart on his sleeve and his boombox held high is the ultimate manifestation of the eviscerated male ego. It’s a human soul laid bare. To many millennial critics, however, it’s the behavior of a self-centered, stalkerish creep who won’t take no for an answer. This disparity in perspective is a fascinating example of how popular entertainment that endures in the cultural imagination over numerous generations can be subject to varying interpretations. It’s also one more reason why so many people think of Say Anything as distinctly Lloyd’s story. Even though Diane’s multiple plotlines drive the narrative, the film’s most emotional moment, and quintessential image, is built around Lloyd. 

The short scene is so powerful in part because of Peter Gabriel’s amazing song. It wasn’t the track Crowe originally planned to use, but when he first put the film together, the scene didn’t really play at all. The simple substitution of “In Your Eyes,” a much-loved hit from 1986, made this moment far more potent than Crowe ever intended. I can’t really fault the picture for having a mid-point scene so effective and memorable that it overshadows all emotional beats that follow, and I would never want to cut this scene or lessen its impact with inferior music, but there’s no question Say Anything’s most iconic moment feels much more about what’s happening for Lloyd than for Diane.

Negative views of Lloyd have also intensified in recent decades because his identity has been co-opted by lonely (sometimes angry) men of all ages who relate to what they perceive as his outsider status, his unwillingness to compromise his values, and his ability to convince someone attractive and seemingly out of his league to date him. What they overlook is Lloyd’s foremost trait: his kindness. He listens to and cares about others. He's surrounded with predominantly female influences, and not only does he reject traditional male attitudes and expectations, he doesn’t even fully understand them—as the Gas-N-Sip scene, in which Lloyd concludes that asking four dudes for their opinions on his love life was “a mistake,” makes clear. Any man who claims Lloyd Dobler as a role model needs to seriously ask themselves if they are truly in the mold of Lloyd, or more like the dateless dickheads sitting at the Gas ‘N Sip on a Saturday night.

For all the reasons I’ve outlined, many people remember the film as the story of a noble slacker who wins over a beautiful, sheltered girl through charisma and sheer persistence. But I maintain that this is not an accurate reading of the plot. Lloyd doesn’t “win” Diane. The circumstances that bring them together have more to do with the IRS investigation that creates conflict and division between Diane and her father, a subplot in which Lloyd is only tangentially involved. When Diane’s world is thrown into discord due to revelations about her dad, she begins to question the foundational truths she’s built her life around. She turns to Lloyd for comfort, understanding, and most of all, honesty—a quality she finds especially appealing for reasons the film makes clear. It’s not that she’s seduced by Lloyd’s charisma, but rather that she falls in love with his integrity and vulnerability.

The film concludes on a note that's certainly meant to be read as hopeful, but it’s by no means clear that Lloyd and Diane will live happily ever after. If they do stay together, we infer, their journey will be bumpy. Like one of his mentors, the legendary filmmaker Billy Wilder, Crowe believes in pithy endings, but this conclusion isn’t like the bows that wrap up many of Wilder’s pictures. That willingness to live with an ungrounded, non-definitive ending is one last thing that sets Say Anything apart from the other classic ‘80s teen flicks like Fast Times, Sixteen Candles, The Breakfast Club, etc, all of which end with an unambiguous conclusion set to a rousing pop song. Lloyd and Diane’s future seems much more fragile. In almost every way, Say Anything defies the tropes of the romantic fantasy it’s remembered as. It's best described as a Gen-X love story, and perhaps the Gen-X love story, in that it best exemplifies the disaffected but optimistic nature of the generation it was made for.