It's been three whole decades since Lloyd Dobler hoisted a boombox above his shoulders outside Diane Court's bedroom window at dawn. It swiftly entered the pop culture canon to become one of the most iconic film moments of all time, right up there with the Psycho shower scene and the "I'll have what she's having" bit in When Harry Met Sally. It's a mental image that will perpetually materialize each and every time Peter Gabriel's "In Your Eyes" comes on an '80s radio station.

But if John Cusack—22 when he played the role that would catapult his acting career—had his way, the seminal teen romance scene might never have happened. Director Cameron Crowe has said in interviews now and back when the film premiered that young Cusack, acutely aware of the cheese-factor, was staunchly opposed to the action. He found it "too passive," Crowe said, and his resistance made shooting the now-immortal sequence particularly tough.

Honestly, "too passive" sounds like a criticism Lloyd Dobler himself would offer. Lloyd, the wry anti-hunk who has trouble articulating what he wants to do with his life except that "I don't want to sell anything, buy anything, or process anything as a career. I don't want to sell anything bought or processed, or buy anything sold or processed, or process anything sold, bought, or processed, or repair anything sold, bought, or processed. You know, as a career, I don't want to do that."

We couldn't help but wonder: Now that Say Anything is officially 30, making Lloyd Dobler roughly 48, what would the lovable underachiever be up to today?

We turned to Cusack for answers.

"I don't know," he says, somehow still thoughtfully. "I never think about sequel stuff. It's like a poem—a story ends."

Fair enough.

You can ask Cusack yourself, should you be so inclined, this Sunday, June 16, when he comes to Houston for a 30th anniversary Say Anything screening followed by a live conversation with the Society for the Performing Arts. He's done this kind of thing in other cities recently, too, and has been for about a year. That's when a company approached him with the concept—successfully employed by other actors from classic fan-favorites like Monty Python—capitalizing on the continued nostalgia of (mostly) Gen X-ers, banking on the fact that people still want to watch and discuss 30-year-old films that mattered, and matter, to them.

Spoiler alert: We do.

"If people want to see them, it's fun for me to walk in and see the house rocking and the soundtrack playing for High Fidelity or Grosse Pointe Blank or Say Anything," Cusack says. "As long as people enjoy it, I'll do it."

(A word about that Say Anything soundtrack, by the way: It's phenomenal, and for more reasons than Peter Gabriel. Fishbones' "Skankin' to the Beat," in a teenage romance, no less? Revelatory.)

It's easy to look retrospectively at a film like Say Anything and deem it quintessential 30 years later. But it was also (mostly) acclaimed back in 1989, too, when Roger Ebert called it "one of the best films of the year—a film that is really about something, that cares deeply about the issues it contains." Not exactly your typical rom-com reception.

And that's what special about Say Anything: Despite the boombox scene—maybe for the boombox scene—it's not cheesy, but earnest; not superficial, but still approachable. We wondered if Cusack and company could tell they were on to something back then. Did he ever foresee the cultural impact we would derive from a sweet, simple story about an oddly matched couple navigating the awkward, fleeting time between high school and the rest of your life?

"You try to make something as good as you can and as genuine as you can, and if you do, usually people at least respect it in some way," Cusack says. "You can tell if a movie is alive, if it has a pulse. That it’s not just a genre, you’re not being sold a Big Mac. I knew we were in that ballpark, but of course you can never predict people would be that enthusiastic."

Does he still talk with his co-stars? Some, yes. He notes that "some of the great people involved," including John Mahoney and Jim Brooks, have since passed away. But he's kept in touch with Ione Sky, who recently had a brilliant comedic turn in HBO's Camping, which we highly recommend to Cusack. He occasionally sees Lili Taylor, who played Lloyd's perpetually brooding best friend, Corey Flood. He stays in touch with some of the crew. And: "I see my sister, obviously."

Lloyd Dobler made Cusack an unconventional, unintentional icon—an alt-darling of sorts—and he went on to achieve similar results with other cult classics, easily falling into the role of the charming underdog. This month, he'll turn 52. And what's he working on now? "Just stuff," he says, in true Dobler form. "I wrote a book not that long ago."

That would be Things That Can and Cannot Be Saida collection of essays inspired by conversations with NSA whistleblower Edward Snowden published in 2016, two years after Cusack met Snowden with co-author Arundhati Roy and Daniel Ellsberg, who leaked the Pentagon Papers in 1971.

Cusack will also star in the upcoming Amazon series Utopia, author Gillian Flynn's (Gone Girl, Sharp Objects) adaptation of a British thriller drama. In his first starring role for TV, Cusack will appear alongside Rainn Wilson and Sasha Lane.

This weekend, though, the past is present, and Cusack hints that, when it comes time for Q&A, everything is fair game. "The audience can ask whatever they want—it can be ridiculous," he tells us. "It'll be fun."

An Evening with John Cusack, 4 p.m., Sunday, June 16 at Jones Hall. Tickets from $39.50.

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