With his third film, Kevin Smith tried to do something new for him: a grown-up film. As loved as it may (deservedly) be, Clerks is remembered for the crude humor rather than the plot, while Mallrats, which was meant to be a smart, amusing teen movie, turned out to be little more than a vehicle for Jason Lee's comedic talent. Chasing Amy is radically different: combining Smith's trademark superb dialogue, believable characters and a heartfelt story, it is one of the best, most insightful romantic comedies of the '90s, and the director's most satisfying picture aside from Clerks I and II.
Whereas his first two movies kept referencing other films as soon as there was time to do so, Chasing Amy centers on Smith's second great passion: comic-books. In fact, it all begins at a convention, where Banky Edwards (Jason Lee) and Holden MacNeil (Ben Affleck) are signing issues of their successful book Bluntman & Chronic. Afterwards, they hang out with fellow artists Hooper X (Dwight Ewell) and Alyssa Jones (Joey Lauren Adams), and while Banky spends all of his time arguing with Hooper over the racism in Star Wars (one of the funniest things Smith has ever written) or the gay subtext in Archie comics, something clicks between Holden and Alyssa, and soon enough they start seeing each other almost every day. It is obvious something deeper than friendship is in the air, and they both know it, yet there's a catch: Alyssa is a lesbian, or at least she used to be one before meeting Holden. Hence the big question: can they have a meaningful relationship with her past being such a huge burden? What kind of sacrifices will have to be made?
In another film, the boy-loves-lesbian premise would have been an excuse to deliver a 90-minute marathon of distasteful, gratuitously explicit jokes. Chasing Amy, on the other hand, is good because it really cares for its characters and whatever crudities there may be never feel excessive or out of place, but on the contrary they manage to convey the speaker's emotions more correctly (this is particularly true for Jason Lee's foolproof, energetic performance). The central love story is honest and touching, two characteristics that are evident in the realistic dialogue and acting: Adams, who hasn't managed to find a decent role ever since, portrays Alyssa as a human being, not a stereotype, and that's what makes her scenes with Affleck, always at his best when working with Smith, compelling and almost painful to watch.
Most of the time, Chasing Amy is a perfect balance between gross-out humor and tender romance, something the director kept toying with on the underrated Jersey Girl (where the jokes were less sweary than usual) and perfected with his masterpiece, Clerks II. There are, however, a few moments when Smith doesn't understand he has to stop and tells us everything about a certain character's personality, whereas he should simply have implied it. Overall, though, this feature remains one of the most hilarious, moving, revealing films of the '90s, with its best moment saved for the director himself: halfway through the movie, the mandatory Jay and Silent Bob (Jason Mewes and Smith) make their appearance. In all the other View Askew flicks, they are just incredibly funny. This time, Bob breaks his silence and gives a long, thoughtful speech that explains the film's title and has more to say about love and relationships than certain movies do in their entire running time. Astonishing.