Above all else, Kevin Smith’s Chasing Amy is an elegy for the foolish lover– a lilting tune for those sad sacks that let a thing of beauty slip through their fingers for reasons even they cannot understand. It is a tragedy about three individuals caught in a maelstrom of emotions they cannot cope with, but also Smith’s sharing of the intimate knowledge that with love there often comes loss and with loss there are often lessons to be learned about one’s self and the life you will lead in the future. Chasing Amy came at a time when Smith was dejected with the Hollywood business model and, turning down several million dollars in budget, Smith made this often uncomfortable but bemusing movie of an authentic tale of love for a quarter of a million dollars and winds up with a deeply personal and soul baring film. Beneath its crude exterior of vulgar, sexually centered humor and buried within its despondent plot, a belief shines through that no matter the heartbreaking misery we so easily suffer by our own misguided hand, life goes on and the prospect of finding happiness is there if we can only accept our mistakes for what they were. Mistakes.

Chasing Amy is such an enterprising and resonant departure for Smith that even with the reoccurring characters and intertwining plot details between it and the other four films of his Jersey series, it stands as a much more grown-up undertaking. Though it is not his finest or even most profound film (That would be Dogma), it is the only one of his ventures where the comedy is secondary to the message, the characters, and romance presented. Chasing Amy is a romantic comedy in the sense that, yes, there are a lot of laughs as Holden (Ben Affleck) tries to woo Alyssa (Joey Lauren Adams). From that perspective Chasing Amy is a romantic comedy just as Clerks is a slacker comedy, Mallrats is a…well… action-slacker-romantic comedy, Dogma is a religious satire, and Jay and Silent Bob Strike Back is a hedonistic, fan favoring, spoof-heavy comedy adventure. But as we watch the romance take root, flourish, then wither, and eventually die, the laughs vanish like ghosts and the whole production begins to seem Shakespearean in nature– just without all the bloodshed. We have two lovers uniting in an affront to some around them (though instead of using skin color or feuding families, Smith makes his female lead a lesbian); we watch jealousy rear its ugly head in both Holden and his best friend, Banky (Jason Lee); and Holden possesses a fatal flaw that brings about his downfall and the loss of that which he’s worked so hard to achieve, that fatal flaw being a heavy dose of pride.

If you have ever seen Kevin Smith out of character in any fashion (and if you have not then I would highly recommend the monstrously entertaining and insightful An Evening with Kevin Smith), you will know that he is generally a soft spoken, witty, but self-deprecating man that employs his crassness and sensitivity equally. The most difficult aspect of Chasing Amy is that after watching it once a second viewing becomes difficult, not only because it makes you mull over any past romantic injustices you’ve been a part of, but because it is an incredibly private look into the heart of Smith himself. His character, Silent Bob, is at his most loquacious in this film and delivers a reflective speech that not only gives the film its title and identifies Holden’s pride, but comes off almost as Smith paying penance for his own past. It is a somber, but enlightening moment.

The characters start out in New York City. Holden McNeil and Banky Edwards, the creators of a popular comic book “Bluntman & Chronic”, are guests at a comic book convention. After a near homicidal autograph session where Banky assaults an irritating collector demeaning Banky’s status as “inker”, the two gravitate towards a guest panel where minorities in the business speak about their place in comic books. It is there the only character more colorful than the sharp-tongued and homophobic cynic of Banky (who isn’t as diabolical as the Bard’s Iago, but who causes quite enough trouble as it is) is introduced in Hooper, the very effeminate homosexual black man that puts on a splendidly comic front as an angry, racially driven radical. After Holden and Banky participate in a staged argument on African American’s in pop culture and a fake shooting occurs to scare off the audience and panelists, the only person remaining is fellow comic book creator Alyssa Jones, who is unfazed by the shenanigans and amiably chastises the trio for their antics. Holden is immediately smitten with her and the four go to a bar where the two hit it off. These two early scenes are the high point of the film’s comedy and the starting point of the air of romance throughout.

The affair is anything but generic. Holden soon finds out Alyssa is involved with another woman and he is forced to resign himself to being her friend only. The chemistry between the two is too powerful for them to handle though, and in a perfectly squirmy scene we wring our hands and bite our lip as Holden pours his heart out to Alyssa and pleads to give him a chance. Initially enraged at his sentiment, Alyssa comes to remember that the original reason she opened herself up to females was so that she wasn’t cutting off fifty percent of the population in the search of her soul mate. She believes Holden might be that person and the two foster an all-too-perfect union. A dark cloud looms over them in the character of Banky, however. Banky harbors an incredible jealousy towards Alyssa, not only because of the chasm forming in his twenty year friendship with Holden, but because underneath the layers of gay jokes and machismo Banky might just be in love with his friend. He succeeds in digging up dirt on Alyssa and reveals to Holden a promiscuous past. When Alyssa admits the truth behind her youthful experimentation, Holden cannot accept the fact that his inexperience does not make him less of a man to her and that no matter her past, he is what she truly wants. And so come the heartbreaks and broken friendships as Holden confronts the two people closest to him about their secrets.

Smith tackles sensitive subjects (or at least what was considerably more sensitive eight years ago) like homosexuality and sexual freedom realistically and intelligently. Smith creates Banky as the lens through which the immature and ignorant would see these subjects, and frank monologues from Silent Bob (Smith’s character), Alyssa, and Hooper (effectively Banky’s foil) share with us viewpoints that would probably make the world a better place if they were more common. It is poor Holden, the everyman– the every-dumb-conventional-thinkingman– stuck in the middle and forced to learn things the hard way.

The cast of Chasing Amy is less important than the characters Smith has written to life. Jason Lee effortlessly upstages his co-stars with his energetic brooding and scathing commentary that cuts to the heart of matters, but it is the fact that his commentary is generally and terribly wrong that allows the viewer to pay more attention to Affleck and Adams. Note the way Banky says, “This is all going to end badly,” early on. It’s so subtle he probably doesn’t even realize it, but he’s not making a premonition. He’s making a promise. Banky’s bile exists because of problems he has with himself, not with the world, and when Banky declares with ostensible frustration that “man-friendly lesbians” are a figment of Holden’s imagination, it feels like the desperate act of a spurned lover.

It is hard to see Chasing Amy as a great romance once the other shoe drops and the hurting begins. You might be asking right now how I could consider it so. Watch it. If Smith has it his way, by the end, you’ll know.