Holden (Ben Affleck), a comic book artist falls for Alyssa. The only problem is, she’s a lesbian.

Chasing Amy (1997) is Kevin Smith’s third film in the loosely linked Jersey trilogy. The first, Clerks, is an ode to generation X slackers stuck working in a menial job. The second is Mallrats, a film that didn’t do so well, and the third is Chasing Amy. This is by far Kevin Smith’s most mature work and in amongst the sexually charged humour a gentle, poignant, and often bittersweet comedy emerges.

Chasing Amy is a romantic comedy set in a world where people write comic books for a living. Their conversations move from the banal to the passionate and even centre on the sex lives of Archie and Jughead. This is a narrative delivered through the funny characters, the realistic dialogue (if slightly hyper), and the clever scripting. This is a Kevin Smith film but it’s a toned down one.

The story follows Holden (Ben Affleck) and Banky (Jason Lee). They’re best friends and have known each other for years. They write a comic book series called Bluntman and Chronic with the inspiration for those characters coming from the equally fictional Jay and Silent Bob. This friendship is one that doesn’t seem to have room for anyone else and when Holden meets Alyssa, cracks begin to appear. Holden and Alyssa kick it off and they seem very well matched but Holden fails to realise that Alyssa is a lesbian.

Clever dialogue and good plotting

You’d be forgiven for reading the plot and seeing some run of the mill sitcom setup. Chasing Amy however is told in the little details and it’s the characters and their conversations that make this an unusual (and often compelling) film. Kevin Smith crafts scenes that are brimming with sharp and ironic dialogue. The skill however is the way that he subtly introduces much bigger and wider issues. It’s in amongst this witty dialogue and bigger themes that Chasing Amy finds its personable and touching tone. This isn’t a comedy about love; instead the focus is on the seriousness of finding a real human connection.

Kevin Smith’s skilled writing

For Holden Alyssa symbolises everything he wants in a girl – but she’s unattainable. It’s this very real obstacle that hinges the plot but there’s also the mirror love story between Holden and Banky. This isn’t a straight up romantic comedy and Chasing Amy reveals a Kevin Smith that has a real skill when it comes to writing. Clerks was shot on a tiny budget of $24,000 and it detailed the lives of two convenience store workers that talked about sex, videotapes, and how terrible work is. Clerks worked because of its well-scripted dialogue and the same can be said for Chasing Amy.

Smith direction in his Jersey trilogy was often obvious and rarely deft. This wasn’t a problem in Clerks but Mallrats really didn’t work. Kevin Smith even apologised for that film at the 1996 Independent Spirit Awards but there’s no apology needed for Chasing Amy. Just like in Clerks, there’s no need for showy direction and Smith’s basic approach serves to highlight the best bits of the film – the acting, characters and dialogue.

Chasing Amy’s real world setting

The depth to Chasing Amy’s narrative is perhaps the most surprising element. It seems that as a film it will exist in a comic universe with comic characters. This isn’t the case and Chasing Amy is placed in a world that feels remarkably real and relatable. Holden’s discovery that Alyssa is a lesbian doesn’t dampen his feelings for her and he realises that he loves her to an extent that he’s never felt before. This is regardless of who she is or what she does – Holden has discovered something close to unconditional love – but it’s unrequited. This isn’t a simple film and the themes that it deals with are complex. Even the most basic characters in Chasing Amy are eloquent when their lives are questioned. In fact Silent Bob, in a perceptive moment advises Holden on the nature of love. It’s always the quiet ones.

This isn’t the story of Holden and Alyssa. In a ‘usual’ romantic comedy that would be the entire narrative. In Chasing Amy it’s about the characters and their increasingly detailed lives all set within a film that could’ve been just a zany nineties comedy. There’s much more to Chasing Amy than a love story and the final scenes strike an interesting chord.

Ben Affleck does well as Holden and he has to make the biggest character and narrative based changes. Jason Lee also does very well as Holden’s sidekick but he’s never relegated to simply that. Banky is a character that’s just as developed as any other in Chasing Amy and Lee keeps his cards close to his chest until right at the end. But it’s Joey Lauren Adam’s Alyssa that really steals the show. She’s bubbly, sexy, and really funny.

This is a Kevin Smith film with most of his usual tropes. The way that they are used however marks Chasing Amy out as a generation X comedy that’s light on the set pieces and heavy on the clever and witty dialogue.