Written and directed by Cameron Crowe (his debut for the latter), Say Anything... was a beloved film from its release on. Unlike some other John Cusack romantic comedies from the same period, this film has aged in a way that isn't problematic.
A lot of this can be attributed to Crowe's heartfelt sensibilities that he brought to subsequent projects like Singles, Jerry Maguire, and Almost Famous. The way he writes his characters makes them seem somewhere between flesh and blood and entertaining caricature. Crowe's films, and the individuals that populate them, feel like a breezy variation of real-life issues, and Say Anything is one of his masterworks.
The Drunk Guy & Lloyd Dobler's Compassion
Towards the end of Say Anything's elongated party scene, Lili Taylor's Corey Flood informs Dobler of how she sees him. They've been friends for a long time, but she's just officially ended it with her jerk of a boyfriend.
To Dobler, a young man she finds trustworthy, she says "I'm a good person. But you? You're a great person." She doesn't say it for the benefit of Diane Court, but rather because she actually means it. Lloyd then shows it by giving a frizzy-haired, inebriated guy a ride home. It's a funny scene because the possibility of the kid puking isn't slim, but it's also indicative of who the film's protagonist is deep down. Like other scenes in the best John Cusack movie, it both furthers the narrative and brings a smile to the viewer's face.
Joan Cusack's Familial Performance As Constance Dobler
Say Anything features John and Joan Cusack as brother and sister, but it's not the only time they've starred in a movie together. However, outside of perhaps Grosse Pointe Blank, this is the best usage of their real-life familial connection.
Joan isn't in too many scenes of the film, but when she is it serves to establish who Lloyd Dobler is (or at least who he thinks he is). She wants her brother to be a positive influence on her son, unlike her ex-husband. He thinks he is a good influence, but, as she points out, he's more playmate than an uncle. This, in and of itself, is an explanation of Lloyd's impending arc.
The Cast
Cameron Crowe's first and perhaps best movie has a cavalcade of reasons for which to recommend it. Nostalgia is towards the top and casting has a lot to do with it. The Cusacks, Lili Taylor, Pamela Adlon, Eric Stoltz, Bebe Neuwirth, and Jeremy Piven all make appearances of varying duration.
The actors behind the Seattle high school's senior class make them seem like genuine people the viewer would like to spend time with. Cusack and Skye carry it, but supporting players make the film's world feel lived in.
Diane Court's Vulnerable Graduation Speech
"I've glimpsed into our future and all I can say is...go back." Diane Court hoped her speech would receive a round of applause at this point, maybe even a few cheers. Instead, she receives crickets.
This is when Court switches to a more direct approach. She elaborates on her outlook regarding the future. She may be top of her class, but even thinking about the future just makes her feel "scared." It's a feeling that any past or present high schooler could associate with.
Lili Taylor's Performance As Corey Flood
Lili Taylor makes a major impression as Corey Flood throughout the first half of the film. She's missing from much of the latter half but still manages to feel like one of the most organic friend characters in an 80s film.
Her role is mostly limited to pining for a jerk, but Corey also gets some of the film's best moments when it's just her, Lloyd, and a third friend. In these more intimate moments, Corey effectively instructs Lloyd on how not to be like her ex. She's a loving individual who has had her heart get broken; She doesn't want to see that happen to a buddy.
The Father-Daughter Relationship
Diane Court's relationship with her father, James, is just as central to the narrative as anything with Lloyd. He's overbearing but loves her more than anything. He's gung ho on securing her future (just as she is), but he's also secretly a crook. This dichotomy ends up serving as one of the most interesting throughlines of the film.
James is also responsible for some of the film's funnier moments. Diane is elaborating on how she spent the night with Lloyd. He was a gentleman, and she decided not to sleep with him. James's face lights up. Then, she says, "But then I attacked him anyway." The light in James's face goes away. Then, in one of the film's best spots of humor, she says, "It always feels good to tell you the truth because if I can't share it with you, it's almost like it didn't happen." The great John Mahoney sells every feeling in a father's arsenal without even needing to speak.
Cusack As Lloyd
"She gave me a pen. I gave her my heart, and she gave me a pen." Cusack delivers the line with a soft smile, the look of someone who has yet to fully accept troubling news.
Say Anything... is easily among the top John Cusack movies if only for how perfect the character of Lloyd Dobler was for him. Cusack could do handsome, gentle, and compassionate better than almost any other star of the 80s. Crowe's film ended up being the ultimate showcase of this persona.
The Iconic Boombox Scene
After Diane gives Lloyd the pen as a parting gift, he's devastated (as is she). He drives his car around crying, goes to his friends for advice, and devises a way to get her back.
His attempt is the stuff of cinema legend, as Cusack's Lloyd Dopler standing with the boombox raised over his head is an iconic image. The song choice, "In Your Eyes" by Peter Gabriel, is absolutely perfect, as well. It's a scene that shows just how much heart Crowe's film has, and why it's so rewatchable.