John Cusack, who has 40 years’ worth of portraying outcasts on his acting resume, will discuss one of his most enduring roles—Lloyd Dobler in Say Anything—in Nashville in November.

Cusack spoke with the Murfreesboro Pulse about Say Anything, how he chooses roles and what it’s like to work with family.

The actor will give a behind-the-scenes look into Dobler, following a screening of the iconic 1989 film Say Anything at 7:30 p.m. Saturday, Nov. 2 at War Memorial Auditorium. (The engagement was originally scheduled for July but was rescheduled because of Cusack’s often-packed filming schedule.)

After Say Anything, Cusack went on to star in multiple popular films including High Fidelity, Grosse Point Blank, Being John Malkovich and Hot Tub Time Machine, among others. Cusack said he has done similar screening and interview presentations of High Fidelity and Grosse Pointe Blank.

He’s Surprised by the Enduring Popularity of Say Anything

Cusack said he is still surprised by the enduring legacy of Say Anything, which has been ranked by Entertainment Weekly as one of the greatest modern movie romances (and #11 on the list of 50 best high-school movies).

Maybe it’s the relationship between Diane and Jim that transcends generations, as well as the thoughts of young love and the idealism of youth, Cusack said.

“There’s this young woman finding out that her father, who she idolizes, turns out to be a flawed human and full of fragility and deceptions. She’s coming to terms with that as she is falling in love,” Cusack said. “That’s her story, and people can relate to finding out that their parents can love them but be terribly flawed.”

He added that Lloyd, the eternal optimist, is perhaps a unique protagonist within Hollywood.

“Certainly, he wasn’t like what you see a lot of characters portrayed,” Cusack said.

Lloyd had an almost un-American worldview. He rejected the individualism and “mythology of capitalism” of American society, Cusack said.

“We have have a culture that wants us to value money and material possessions more than each other,” he said, adding that Lloyd was more interested in “wanting to get to the truth” of life and a more meaningful existence.

“I think there are probably elements of that that make it endure a little bit because those elements are around today,” Cusack said. “I don’t know if that’s the truth. I find it interesting that people still like it 30 years later. People change and tastes change but this doesn’t seem to be the case [with Say Anything].”

He Roots for the Underdog

Cusack often choose roles where he plays the underdog or a person outside of conventional society, as seen in some of his most popular roles.

He said he’s drawn to these roles because he doesn’t like to root for winners.

“It could be the worst thing in the world to be on the side of people who’ve got it all. I like the outcasts,” Cusack said.

And does he look at himself as an outcast and someone worth rooting for?

“I’d say so, probably. Yeah,” Cusack said.

But Cusack doesn’t just imprint himself on his roles, they also have an impact on him.

The actor took up Lloyd Dobler’s pastime of kickboxing before Say Anything to train for the role. He eventually became a six-degree black belt.

He Likes Working With His Sister

Cusack has co-starred in nine movies with his sister Joan Cusack.

He added that having a sibling bond makes working together on set easier.

“It’s super-easy to work with people you know because you have that familiarity and shorthand. Maybe will we get to work together again.”

While she wasn’t in Say Anything, she did play Marcella, the secretary to Cusack’s reformed assassin Martin Blank in Grosse Pointe Blank.

“That was the funnest, getting to work together on a film like that,” Cusack said.

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For more information on Cusack’s appearance in Nashville, visit tpac.org.