5) High Fidelity
There are few actors who possess the inherent likeability of someone like John Cusack. High Fidelity operates on this assumption, and it succeeds on the merits of such, because the character in the movie is kind of a douche at times but our loyalty to him never really wavers. Maybe part of it is because he’s confiding in us and so we want to be a good friend, even if we’re captive listeners. Most of it is because he’s so damn charming and his observations can be insightful and humorous.
Possibly the greatest joy of the movie though is watching Jack Black before he was crazy bearded icon of buffoonery that is the Jack Black of today (although he still manages to do interesting work; see: Bernie). Here he’s not a cool party animal. He’s a manic record store employee that is obnoxious and annoying. It’s funny to see him be rude to customers, but you also realize he’s kind of an ass. His character Barry is beautifully counteracted by the meek and soft-spoken Dick. Their relationship is a riot, but the key relationship between the Cusack character Rob and his on-off girlfriend Laura is the heart of this thing, and provides us with both truthful insights into relationships and a satisfying conclusion.