In post-production on Mallrats, Kevin Smith began dating actress Joey Lauren Adams, who had played a small role in his second feature, and consequently decided to write her a starring role in his third film, that would become Chasing Amy. Who would have guessed that such a decision motivated by personal romance would deliver what could still rank as Smith's strongest and most mature piece of work? Clerks put him on the map, small scale, as a writer with an ear for dialogue & capturing the small-town American ideals of slacker lives & unfulfilled dreams. Mallrats then heightened the comedy, added farce, and became a comic-book version of that concept. Chasing Amy feels like a confluence so far of all the styles Smith was trying, and indeed of all the points he's been trying to make about relationships and, crucially, the recurring theme of men especially not understanding women. It's a confident, laid back picture.

As with his two previous lead male characters, Smith brings a strong dose of himself to Ben Affleck's comic book artist Holden McNeil, a man on the cusp of material success being held back ironically by his own lack of imagination, experimentation, his stiffness, all of which is brought into focus when he meets Adam's Alissa, much more of a sexy, sassy free spirit who he falls instantly, madly in love with... and who turns out to be gay. Now Smith could quite easily have written a film about Holden pining, about him desperately trying to convert Alissa, but it's a far more interesting move to have her reciprocate & then tip the scales unconventionally in that it's the male who is hung up on quite what such a massive personal change does to their friendship & relationship. It allows Smith to hit sexuality far more head on than his previous films did, and the benefit of Affleck is that he's perfect in this kind of role - a little uptight, a little preppy, not quite likeable but also someone you hope will get the girl. Jason Lee wouldn't have worked this time around & fits far better his comic book partner Banky, possibly a closet homosexual who feels a distant cousin to Lee's character in Mallrats for his outspoken, bullish nature in the face of the 'alien' concept of lesbianism & gay life, which Smith can explore through him. With Holden it's different, it's not that he can't accept gay people, he just can't accept the promiscuity that comes with it.

That's in many ways where Chasing Amy falls a touch into stereotypes, of which it has been accused plenty. Adams doesn't really do the lesbian community any favours given how easily Alissa gives up her gay life after finding a man to be the missing piece of the puzzle, though in fairness to Smith he never quite makes the gay angle the ultimate point - the problems stem far more from Holden's own demons about the past, the classic point that you should never find out what (or who) your partner did before you, as it bound to cause problems. Smith though isn't the most subtle of filmmakers and his treatment of the gay angle is simplistic, even if you sense he's well aware of that by throwing in Dwight Ewell as not just a very outwardly gay artist, but a black man as well - a 'twofer' on the controversy scale. That's not to say his film is satirical, that's lending praise where it isn't due - it's certainly his most rounded, well performed and confidently scripted piece yet, and he pulls back the comedy away from the farce of the previous film (and indeed he makes a point of suggesting the events of Mallrats may well have been a product of Holden's imagination, even if it's throwaway - but it would explain the tonal shift of that film, retroactively). It's slower, it's longer, and though it may not be as funny as either of his previous movies, it's deeper, it means a little more & it feels like a writer/director starting to find his voice.

You wouldn't quite place Chasing Amy up there with the defining romantic comedies of the 90's, of the laid back, slacker variety anyway - it's not quite distinctive or memorable enough to rest alongside that category. Kevin Smith however has rarely since got under the skin of his characters or subject matter in the same way he does here - subsequent outings have largely tipped deeper into the melodrama or silliness or farce of Mallrats, whereas here he genuinely creates a piece of work that's both funny, quite sweet in places and has something to say on sexuality, on the male psyche, and the way we perceive homosexuality itself. It could well be remembered as Smith's best movie, or close to it.