What It's About:
Lloyd Dobler (John Cusack) is a high school graduate with no real direction, other than the certainty that he doesn't want to "buy, sell, or process anything" as a career. Diane Court (Ione Skye) is the high school valedictorian on her way to study in England on a prestigious fellowship. She agrees to go out with him to an epic annual graduation party, and their summer romance proceeds from there. Her relationship with her father, whom she chose to live with after her parents divorced, complicates matters. He doesn't like Lloyd because he sees him as mediocre, someone whose only ambition is kickboxing and spending as much time with Diane as possible. Diane's father (John Mahoney) is also under investigation for his management of the nursing home that he owns, which puts further pressure on Diane in terms of her future. How will it all end? If you haven't seen this gem of a movie, which Entertainment Weekly selected as the Best Romantic Movie since the mid-1980s, then take this Valentine's Day to watch it; you (probably) won't be disappointed.
Why It's Worth Watching:
First of all, it's a reversal of the typical rom-com trope. Diane is the one who has it all together, the drive, the ambition, the direction, the bright future. Lloyd is her supporting character; all he wants to do is provide her with love and support so she can succeed. As he tells her father, "I want to be with your daughter. I'm GOOD at it!" Lloyd's love is true but also honest; Diane is, in the words of Lloyd's best friend Cory (played brilliantly by Lili Taylor), "a brain trapped in the body of a game show hostess." But he's so sweet to her in so many small ways, you get to experience Diane falling in love with him as the film progresses. Without spoiling some important details, ...say anything sets up some plot lines that you expect to go one way, but then the exact opposite happens, and it's so surprising and refreshing.
Writer and director Cameron Crowe puts in so many careful details, like the graduation party, which looks and feels exactly the way a high school kegger actually was (not the comic John Hughes version), that you're eager to see where this story is going to take you. It's eminently quotable in a hundred different ways. Add to that the brilliant soundtrack, scored by Heart's Nancy Wilson (Crowe's wife), featuring an eclectic mix of late-eighties tracks as well as the most iconic boombox lift in movie history—there's hardly any amount of praise that I cannot laud upon this film.
What in it for Her:
As I said, Diane is not merely the female romantic interest to Lloyd; she's the character with the most to gain and the most to lose. There are dozens of reasons why she shouldn't fall for Lloyd; she even mentions some of them to him out loud, and they become the rationale for their mid-movie breakup (romantic movies always have a breakup, after all). It's refreshing to see the female half of a romance movie relationship be her own person instead of simply an accessory to the male lead. Ione Skye makes teenage ambition mixed with apprehension seem all the more real with her performance, showing both strength and uncertainty in equal portions.
What in it for Him:
John Cusack is, for me, the ultimate movie bro. Throughout his career, all of his roles have seemed so relatable to myself and my own life experiences. I should mention another teen romance movie he starred in, The Sure Thing, which was Rob Reiner's directorial debut, which I considered for this list as well (it's great, watch it as a bonus!). This movie will bring back memories of high school loves both fond and foul for most guys. Best dude moment: pining for Diane after their breakup, he asks his guy friends for advice, none of which is useful. Then he asks them to justify their advice...just watch:
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