Chasing Amy (1997): Kevin Smith Best Film? Starring Ben Affleck

Inspired by his 1994 Sundance Film Fest encounter with director Rose Troche and the cast of Go Fish, a seminal lesbian romantic comedy, Chasing Amy redefined the boy-meets-girl formula for a culture where anything goes, particularly sexual orientation.

“I’m a jaded optimist looking behind the doors of small-town America,” says director Kevin Smith. Peeping behind closed doors links him to Lynch’s Blue Velvet and Lost Highway, though Smith is peering with humor as opposed to menace or bizarreness. Smith is one indie director not seduced by film noir and its somber fatalism. How could he be “My generation believes we can do almost anything. My characters are free: no social mores keep them in check.”

Depicting the stormy, unlikely love affair between two comic-book artists, the twist of this spiky film is that the guy is straight and the girl isn’t. Smith turned the lighthearted, sexually charged material into an emotional drama. Deliberately designed to confound expectations, the film begins with the most outrageous lesbian stereotypes–only to explode them.

Once again, Smith centers on yearnings–forlorn layabouts looking for love. The title derives from a monologue delivered by Silent Bob–a recurring character in Smith’s films, along with Jason Mewes’ druggie Jay–who mourns the girl that got away. A comedy with serio overtone, Chasing Amy is about sacrifice, or how much one is willing to give up for love.

The lovestruck Holden (Ben Affleck) shares his place with his buddy Banky (Jason Lee) in central New Jersey; they’re like college roommates who refuse to mature. The creators of a popular comic book, Bluntman & Chronic, they enjoy a laid-back partnership, marked by intuitive understanding and constant sparring. Alyssa (Joey Lauren Adams), the comic-book artist Holden falls for, is lesbian.

It takes a lot of “pseudo-dates”–as Banky sneeringly says–for the two to connect. Banky serves as a jealous ex-suitor, always presenting the negative side. It also takes some byzantine sexual maneuvering before Alyssa realizes she’s in love with Holden.

At first, the cynical but romantic Holden can’t believe Alyssa remains sexually unresponsive, but when he finally breaks down and confesses his love, she’s furious. For him, to be in love is easy, but for her, it means change.

The irony is that it’s Holden’s life, not Alyssa’s, which needs to change the most. Holden’s curiosity about lesbian courtship and sex (what women do together in bed) begins as leering, but then changes into genuine interest. Holden is not upset by Alyssa’s lesbianism, because he perceives her love for him as renunciation of that past. What disturbs him is Alyssa’s heterosexual experience (in high school, she had sex with two guys at once), based on his desire to be the first man in her life. Holden’s double standard can’t tolerate Alyssa’s promiscuous past.

As the critic Peter Rainer observed, Chasing Amy is about a guy who’s forced to face up to his own square expectations and to reluctantly acknowledge that he is not as hip as he thought.

Like Clerks, Chasing Amy is a politically incorrect comedy with casual profanity, but more profoundly so. To his credit, Smith isn’t playing out the stereotype that lesbians are women who haven’t met the right guy. And he shows respect for women, thinking, as the Manohla Dargis pointed out in the L.A. Weekly, that a woman’s mind is as sexy as her body.

Nonetheless, though honestly conceived, Chasing Amy still reflects a naive, outside view of lesbianism by a white heterosexual male. Curiously, once Alyssa is committed to Holden, she never again experiences doubts about her sexual orientation, and never even shown to even entertain the thought of having sex with another woman.