Now this list has finally arrived at a Kevin Smith film that was greeted with a positive critical reception, and deservedly so. Released two years after Mallrats, Chasing Amy was a much more mature proposition, exploring gender roles, sexual experience and the boundaries of friendship, all wrapped up with Smith's trademark snappy dialogue and raunchy humour. It won two awards at the Independent Spirit Awards in 1998: Best Screenplay for Smith and Best Supporting Actor for Jason Lee. The plot revolved around the relationship between Ben Affleck's Holden McNeil, a comic book creator, and Joey Lauren Adams' fellow creator and lesbian Alyssa Jones. Holden is attracted to her and when their friendship deepens, can't keep his feelings in and confesses his love to her. They then begin a relationship, but tensions mount between Holden and Banky (Lee), his co-creator on the comic book. Banky doesn't trust Alyssa and digs up dirt on her sexual past, which leaves Holden feeling insecure and affects their relationship. The film features a brilliant monologue from Silent Bob, the only time he speaks for any real length of time in the View Askew movies. While some may argue that it is disingenuous for Smith to give himself the best piece of dialogue in the film, the story he tells of "Chasing Amy" is undoubtedly emotionally charged and has pertinent things to say about the nature of romantic relationships.
