‘Say Anything’ at 35: How a Boy, a Boombox and a Dream Turned Into a Timeless Classic [Retrospective]

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In 1989, Cameron Crowe made his directorial debut with the teen romance, Say Anything…. In which John Cusack’s Lloyd Dobler, a directionless cutie, falls for Ione Skye’s Diane Court, the aloof yet beautiful class valedictorian. Lloyd is instantly recognizable—a relatable figure from high school, not a typical jock but one of the guys, endearing by not being cookie-cutter attractive. Diane Court is an enigma to him and most of her classmates, consumed by academic pursuits and familial obligations, known but not truly friends with anyone. This isn’t your typical “popular guy falls for the nerdy girl” or “good girl fixes the bad boy” story. Lloyd may lack direction beyond his relationship with Diane, but he’s undeniably a sweetie pie. Diane’s closest friends may be the elderly folks at her father’s nursing home, but she’s still very much an object of desire and interest for Dobler and his graduating class; she’s not going to be taking off her glasses, shaking out her hair and revealing a surprise hottie. Crowe, Cusack, and Skye navigated these tropes to create a generation-defining film. 

I didn’t discover Say Anything… upon its release; at the time, my main interests were He-Man and the World Wrestling Federation (What can I say? I’ve always had a thing for homoerotic muscle twunks). A decade later, in high school, a glowing review in Entertainment Weekly caught my eye. A or A+ reviews were rare – I didn’t know that they were even allowed to give such high praise. Worried about the writers at EW being tracked down by the movie police and intrigued by the film, I finally picked up the video box I had passed by innumerable times when roaming the racks at my local Blockbuster Video. The only thing that would make this paragraph more 90s-coded would be me having The Rachel at this time. And maybe I did. I’ll never tell. 

I fell in love with Say Anything…, watching it regularly with my friend Meghan and quoting it incessantly (“You must CHILL!”). It became a cornerstone of my high school and college years, mirroring my own teenage thoughts, hormones, and drama with significantly better writing. To me, Say Anything… isn’t just a well-told love story; it was the first time I can remember watching something that reflected my own experience back to me, deepening my love for movies. 

Something to Crowe About

By the age of 25, Cameron Crowe was already a teen journalist for Rolling Stone,  and had penned the screenplay for another 80s teen classic, Fast Times at Ridgemont High, adapted from his own novel. His talent caught the attention of James L. Brooks, who, along with the legendary Polly Platt, produced Crowe’s directorial debut.  Subsequently, Crowe embarked on one of the great writer-director film streaks: Singles (1992), Jerry Maguire (1996), and the self-referential classic Almost Famous (2000). From Say Anything… to Almost Famous, Crowe emerged as one of the premier writer-directors of his generation, endorsed by none other than James L. Brooks, living in his post-Terms of Endearment and Broadcast News world and about to change television forever with The Simpsons.

Catch me on the right day and any one of those films is my favorite Crowe, but today it’s probably: Say Anything…, Almost Famous, Jerry Maguire, Singles.

Following the success of Almost Famous, for which Crowe won his first (and only) Oscar, he reunited with his Jerry Maguire co-star, Tom Cruise, for the intricate (or intricately bad) Vanilla Sky. His output from 2005 to 2015 failed to reach the heights of his 90s work, with films like Elizabethtown (2005), We Bought A Zoo (2011), and Aloha (2015) receiving lukewarm reception. Aloha was particularly rough, with Emma Stone’s public apology from the audience of the Golden Globes years later being the best thing about it.

Despite the struggle to replicate the success of his earlier films, I haven’t lost hope that Crowe still has one or two compelling stories left to tell. Notably, Crowe has not helmed a narrative film since Aloha, symbolic as “Aloha” means both “hello” and “goodbye.”

“Lloyd Dobler, Alright”

Unto each generation a young man adrift in ennui or lacking direction is made an icon. The 50s boasted James Dean in Rebel Without a Cause, the 60s had Dustin Hoffman in The Graduate, and the 80s crowned John Cusack as Lloyd Dobler in Say Anything…. Admittedly, it’s a stretch but if you squint hard enough, you can see the thread from Benjamin Braddock learning “plastics is the future” to Lloyd Dobler sharing his shaky life place to Diane Court’s father (John Mahoney):  “I don’t want to sell anything, buy anything, or process anything as a career.”

(Note from the author: It’s worth noting that John Cusack once blocked me on Twitter for tweeting during the Boston Red Sox’s appearance in the 2016 World Series. As a professional, I assure you this interaction will not compromise my journalistic integrity.)

At this juncture in his career, John Cusack had become best known for a string of teen comedies that established him as a promising hot young thing. But Cusack as Lloyd Dobler is the casting alchemy that turns actors into movie stars; it’s difficult to envision any other actor of the time embodying Lloyd Dobler.  Cusack infuses Lloyd with just the right blend of restlessness, aimlessness, and tenderness, defining him as an authentic, genre-defining sweetheart. Despite their initial lack of acquaintance and possibly never having spoken, the film opens with Lloyd already smitten with the unattainable Diane Court. Cusack drops us right in the middle of those feelings, rooting for him from the outset. It stands as one of the most effortlessly charming performances ever captured on screen.

 A Who’s Who of 80s Stars

Say Anything… is one of those movies that you watch now and constantly do the Leo pointing at the screen meme when another familiar face pops up on screen. From the jump they’re giving us none other than Frasier’s dad himself, John Mahoney, in a purposefully bad dye job (he’s got to keep up appearances!). Funny enough, Frasier’s ex-wife, Bebe Neuwirth is also in the movie! We also get the fifth (of ten!) pairing of real-life sibling John Cusack with his sister Joan, who makes every film just a little better. Of course, Jeremy Piven shows up as is and will continue to be contractually obligated for all John Cusack films. 

Lloyd’s female best friends are played by Better Things creator-genius Pamela Adlon and scene-stealing Lili Taylor, whom I have no doubt I would have stumped for in the Best Supporting Actress race in 1989. The trio is rounded out by Amy Brooks, daughter of James L. Brooks and the producer of last year’s terrific Are You There God? It’s Me Margaret adaptation. 

So many more familiar faces pop up like Chyna Phillips (1/3 of Wilson Phillips), Eric Stoltz hot off not being Marty McFly, and classic “oh yeah that guy” character actors Loren Dean, Gregory Sporleder and Richard Portnow. Producer Polly Platt even gets a cameo!

But of course, this is the year 1989, so the most delightful surprise is both Heather Chandler (Kim Walker) and Heather McNamara (Lisanne Falk), two of the three titular Heathers roaming around the graduation party all our characters attend. The very specific thrill of seeing Heather Chandler and Diane Court interact with one another is only exceeded by my need to have the third Heather, Shannen Doherty, in the mix.  

Court-ing Disaster

In some ways, Say Anything… is a romantic comedy between father and daughter. If you were an alien dropped onto this Earth and given this movie to watch with no concept of normal human relationships, you would think it was about a love triangle between Lloyd, Diane and Diane’s father, James. Diane and James’ father-daughter chemistry is sweet, but their chemistry as more than just family? It’s electric. 

I have seen this movie 50 times; I have to believe this dynamic is intentional. 

There’s no way you can write and direct a scene like the one in which Diane and James host a dinner party (for mostly James’ middle aged friends) and tell an intricate story about her fear of flying, complete with a rat-tat-tat cadence and completion of each other’s sentences. They essentially function as long-term husband and wife for most of the film— and not estranged husband and wife. This is a couple who still make time for each other at least once a quarter. 

When it’s discovered that James has been stealing from the elderly people in his care at his nursing facility, it’s hard not to think of Erika Jayne and her husband, Tom Girardi, for example. Diane’s disappointment is one thing, but her level of betrayal is quite another. It’s that of a scorned woman. I will die on this hill. 

That said, it’s a testament to Crowe’s screenplay as well as Ione Skye and John Mahoney’s performances that this all somehow makes sense. Diane chose to live with her father after her parent’s divorce, after which their only goal was to get Diane to succeed, excel, and advance. They were in it together, causing James to swindle the elderly to pay for Diane’s education and Diane to not interact with anyone her own age for most of her high school career. They become each other’s “person”… and possibly more (OK, I’ll stop). 

Diane Court – or Ione Skye – didn’t quite become the icon that Lloyd Dobler ended up being mostly because she never held up a boombox in front of her own window. Oh, and also, misogyny. But Diane Court is a real breath of fresh air: She’s smart and beautiful, sure, but she’s also funny and determined and not going to derail her life plans for some guy, no matter how good an amateur kickboxer he is. Despite teenage women in film not being canonically horny just yet, Diane initiates their first time having sex in one of the sweetest virginity loss scenes put to film. She’s Samantha, Miranda, Carrie and Charlotte all mixed into one. Sorry, Gen-Z!

The Boombox

There’s a good chance if you’ve never heard of Say Anything… you are familiar with The Scene. The film’s most lasting iconography is of John Cusack as Lloyd Dobler standing in front of his car, boombox raised, blaring Peter Gabriel’s ‘In Your Eyes.’ It is one of modern movie history’s most famous -and replicated – scenes. Maybe it was from a poster, a movie montage, or a parody, but chances are you’ve seen this scene play out somewhere. If nothing else, dorm room walls were never the same.  

It turns out that producer James L. Brooks understood the potential impact this scene could have and pushed Crowe to keep it in. Cusack was also hesitant about the moment but ultimately admits that he, Gabriel, and Crowe are part of film history. 

In the movie, with mounting pressure from the IRS rattling her father and her fellowship across the pond starting imminently, Diane breaks up with Lloyd. In one of the film’s best scenes, Diane gives Lloyd a pen, asking him to write to her. When Lloyd calls his sister from a phone booth drenched in rain natch, he delivers the devastating line: “I gave her my heart and she gave me a pen.” We are all shattered. 

Lloyd takes the break-up… not great. With echoes of Romeo and Juliet running through our heads, Lloyd makes his last-ditch effort to get Diane’s attention by raising that boombox. It worked! Diane realizes she’s got a great guy on her hands, kind of sort of forgives her now incarcerated father, and faces her fear of flying with Lloyd by her side. 

The perfect end to a perfect film.

Say Anything was released on April 14, 1989 by 20th Century Fox. It is currently available to stream on Hulu and rent or buy on Prime Video.