“What I really want to do with my life—what I want to do for a living—is I want to be with your daughter. I’m good at it.”
Scruffy underdog wins the heart of the most popular girl in school. That’s a story that played out a lot in the 80s and 90s, but Say Anything manages to go deeper than most other films that follow this formula. Directed by Cameron Crowe (Almost Famous, Jerry Maguire) and starring John Cusack and Ione Skye, this film is simultaneously a teen love story and a metaphor for Generation X coming of age. It was for Gen X what The Graduate was for Baby Boomers and what Lady Bird was for Millennials: a chance for them to define their relationship with the previous generation, on their terms. The 80s were a time of great financial growth and security, but also rampant corporate greed and some unscrupulous actions, and Gen X had become old enough to say something about it. But it’s also a great teen love story with emotional depth and humor. Is this the perfect teen movie? If not, it’s awfully close.
The plot follows Lloyd Dobler, an aimless but lovable young man, as he graduates from high school and decides to pursue Diane Court, the valedictorian. The two surprisingly hit it off really well and get to know each other quickly, but there’s a catch: Diane is set to move off to Europe at the end of the summer for an amazing academic opportunity. Diane’s father, James, is a wealthy owner of a retirement home who’s unsure what to think of his daughter’s new relationship. When James comes under investigation by the IRS, it threatens the stability of his relationship with Diane—and Diane’s relationship with Lloyd.
How many of them really know what they want, though? I mean, a lot of them think they have to know, right? But inside they don’t really know, so… I don’t know, but I know that I don’t know.
Say Anything crafts a subtle metaphor for Gen X growing up and having something to say about their parents, and it does this very well. Though the story focuses on Lloyd, it tells a story much like that of The Graduate: a young person caught in the middle of two cultures—in this case, Diane Court—must choose which one she wants to start her new life with. The film does a great job of showing how each of these relationships works and how each of them falls short. James Court has placed a high priority on wealth, but he really loves his daughter and wants the best for her. On the flip side, Lloyd Dobler is one of the most likable teen characters to ever grace the screen, but he definitely does not have life figured out yet, especially when compared to his new girlfriend. James and Lloyd are nearly the opposite of each other, but each of them loves Diane in their own way and each is shown to have value. It does a great job of setting up the culture clash without being too heavy-handed as many later Gen X movies would be.

But as I said, this is also a fun movie, with humor on par with later Crowe films like Almost Famous. There are a few hilarious moments, but there are also a lot of moments that just feel good—not laugh-out-loud funny, but they’ll bring a smile to your face, such as when Lloyd is teaching Diane how to drive a stick-shift. Lloyd’s friend Corey is like a prototype for every edgy young woman that would show up in film throughout the 90s, and she’s almost as likable as Lloyd. Lloyd’s relationship with his nephew is both heartwarming and hilarious. And Lloyd’s failed attempt to integrate with traditional guy culture had me laughing too. There were so many things this film did right.
Say Anything really captured the more endearing attributes of Gen X while not shying away from the culture clash between them and the Baby Boomers. I’ve always loved this story, even now that I’m almost twice as old as Lloyd was in the film, and it will always be one of the anthems of my youth. Whether you’re Gen X or any other generation, this is a great coming-of-age story that captures youth, young love, and independence better than most films. As the film’s tagline said, to know Lloyd Dobler is to love Lloyd Dobler, and the same is true of this film—it’s really hard not to love this movie.
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Runtime: 1:40
Director: Cameron Crowe
Year: 1989
Genres: comedy, drama, romance, teen
Rating: PG-13