Some movies don’t just capture a time; they capture a feeling. Say Anything (1989) is one of those rare stories that feels as honest today as it did more than three decades ago. In this episode of The Shermer High Alumni Association, Kristin, Jeannine, and Carole revisit Cameron Crowe’s quietly powerful love story that helped define what sincerity looked like in an era obsessed with irony.
John Cusack plays Lloyd Dobler, a kindhearted underachiever who sees the world differently from his peers. He’s no prom king or future CEO—he’s just a guy who knows what he wants, even if that something doesn’t fit anyone else’s idea of success. When he falls for Diane Court, the class valedictorian played by Ione Skye, their connection feels genuine, awkward, and deeply human. Against her father’s expectations and the uncertainty of growing up, Diane chooses to take a chance on the one person who sees her as more than perfect grades and good manners.
The hosts reflect on what makes Lloyd so enduring: his openness, his lack of pretense, and his refusal to play games. He’s not the bad boy or the jock. He’s just a young man trying to do the right thing, even when it means holding a boombox over his head in the middle of heartbreak. Kristin describes Say Anything as “pure sincerity. No gloss, no easy answers—just emotion,” while Jeannine points out that “Lloyd’s not cringe; he’s honest. That’s what makes him rare.”
Throughout the conversation, the hosts discuss how the film’s themes of honesty, bravery, and first love feel more relevant now than ever. Diane’s relationship with her father, played by John Mahoney, adds layers of complexity that most teen films of the 80s avoided. His warmth masks something darker, and his moral collapse forces Diane to see the world—and her future—with painful clarity. The honesty in those moments, the podcast notes, is what elevates Say Anything beyond a high school romance.
The episode also explores the film’s legacy, from its unforgettable soundtrack featuring Peter Gabriel’s “In Your Eyes” to Roger Ebert’s praise calling it “one of the best films of the year—a film that is really about something.” Say Anything earned near-universal acclaim and remains a defining piece of Generation X storytelling.
By the end of the episode, all three hosts agree that Say Anything belongs in the Shermer High Hall of Fame. It earns a zero on their Cringe Meter—a rare distinction for any 80s movie—and a permanent spot in their cinematic hearts.
As the show closes, the hosts remind listeners why this film still resonates: Say Anything stays with you because it reminds you of who you wanted to be. It doesn’t promise perfection or easy answers. It just asks you to show up for the people you care about, even when it’s hard.
Synopsis
- Say Anything… is a 1989 romantic comedy-drama about an unlikely summer romance between a high school “underachiever” and the class valedictorian.
The story follows Lloyd Dobler (John Cusack), a good-hearted and optimistic aspiring kickboxer, as he attempts to win the heart of Diane Court (Ione Skye), the brilliant, beautiful, and sheltered top student of their graduating class. Against all expectations, especially those of his friends, Diane reciprocates his feelings.
Their romance blossoms over the summer, but their differences and the pressure from Diane’s overprotective and doting father, James Court (John Mahoney), pose a major challenge. The relationship is further complicated by Diane’s prestigious fellowship to study in England at the end of the summer and the revelation of her father’s criminal investigation by the IRS for embezzling funds from his retirement home.
Under pressure from her father, Diane eventually breaks up with Lloyd. This leads to the film’s iconic scene, where a heartbroken Lloyd stands outside Diane’s window holding a boombox over his head, playing Peter Gabriel’s “In Your Eyes”. Diane ultimately discovers the truth about her father’s actions, leading her to reconsider her relationship with Lloyd, the one person she has come to trust.
The film explores themes of first love, the transition into adulthood, and the difficult choices faced by young people at a crossroads in their lives.
Actors & Crew
- John Cusack is an American actor and activist with a career spanning over four decades and more than 80 films. He’s known for his roles in 1980s coming-of-age movies like Sixteen Candles, Better Off Dead, and Say Anything. Cusack is known for being outspoken about Hollywood, the US government, and war. He’s also known for working with his family, including his sister Joan Cusack, in his films.
- Ione Skye Lee is a British-American actress, author, and artist. She’s best known for her role as Diane Court in the 1989 cult classic Say Anything…, starring opposite John Cusack. Skye’s other film credits include Wayne’s World, Gas Food Lodging, One Night Stand, and Fever Pitch (2005). She also had an uncredited role in Zodiac (2007). In 2006, VH1 ranked Skye 84th on their list of the 100 Greatest Teen Stars.
- John Mahoney was an award-winning American actor. He was born in England, the seventh of eight children. Long interested in acting, Mahoney didn’t make the transition to his craft until he was almost forty years old, and in 1986, Mahoney won a Tony Award for Best Featured Actor in a Play (The House of Blue Leaves (1987)).He was best known for playing the role of the father of the eponymous character Frasier. He later concentrated on stage work back in Chicago, where he passed away in 2018.
- Also of note: Joan Cusak, Jeremy Piven, Pamela Segall, Bebe Neuwirth, Eric Stolz.
- Also, also….music: Living Colour, Cheap Trick, Red Hot Chili Peppers, Peter Gabriel obvi, Depeche Mode, Fishbone,
Critical Reception, Rewatch verdict and Cringe Meter
Say Anything… was well reviewed. Rotten Tomatoes has approval rating of 98% and 85% on the popcornmeter.. The website’s critics consensus reads, “One of the definitive Generation X movies, Say Anything is equally funny and heartfelt—and it established John Cusack as an icon for left-of-center types everywhere.“
Giving the film four out of four stars, Chicago Sun-Times film critic Roger Ebert called Say Anything… “one of the best films of the year—a film that is really about something, that cares deeply about the issues it contains—and yet it also works wonderfully as a funny, warmhearted romantic comedy.” He later included it in his 2002 Great Movie list, writing, “Say Anything exists entirely in a real world, is not a fantasy or a pious parable, has characters who we sort of recognize, and is directed with care for the human feelings involved.”
In a less positive review, Variety called it a “half-baked love story, full of good intentions but uneven in the telling.” But, the review also said the film’s “[a]ppealing tale of an undirected army brat proving himself worthy of the most exceptional girl in high school elicits a few laughs, plenty of smiles and some genuine feeling.”
Jeannine: 0/5 – Watchingon a Saturday
Carole: 0/5 – Watching on a Saturday
Kristin: 0/5 – Watching on a Saturday INDICTED INTO THE SHAA HALL OF FAME
