Bottle Rocket's plot isn't very heavy. Doesn't need to be; for Wes Anderson's first film he takes partly (in theory) a cue from Michael Cimino's Thunderbolt and Lightfoot. There too were the real oddball outsider characters, looking for a leg up but not with the same kind of zeal of a real hard-bitten criminal or neo-noir. In Bottle Rocket there's an ex-volunteer at an insane asylum and a guy who works for a landscaping company and the two are thick as thieves- only they're not good at actually being thieves, with one or two moments of exception. And yet Anderson doesn't mine for the easy parts for comic effect. His sense of humor is in the small things, little character traits or a moment that pops out.
It may depend on how one sees the characters, and how much one is a fan of the Wilson brothers, Luke and Owen. But what Anderson does capture is that innocent feeling of being unsure of life and the things that make friendships kind of awkward at times. The three "criminals", played by Anthony, Dignan and Bob bicker and converse and do whatever like normal folk, not real gangsters like, say, Mr Henry (James Caan), but they aspire to that, and Dignan gets the closest. Meanwhile, on the lam from a robbery of a bookstore, Anthony falls for a Peruvian housemaid and Bob has his own worries with his backyard pot growth. Their appeal, really, is in how the interactions are based around a solid theme of loyalty and friendship, and the film-making takes it to another level.
It's hard to say if I found this a really great comedy- there's a few big laughs, one with a hilarious botch during a climactic robbery with a shot at someone unexpected, and little ones like a PB&J just lifted off the ground or a bad encounter at a country club- but it's an unusually amazing heist-character-drama. Well, drama of sorts; it's the Wes Anderson style already in full mode, and it's exhilarating to watch him make 90 minutes feel a lot fuller, a lot more alive than most at such a running time. I also liked the Wilson brothers, with the both of them in their breakout roles completely on top with their subtle, zany and quietly crazy roles. Loved the music, the cinematography, but most of all the emphasis on character over plot. In heist movies, or just young/lost-20-something generation movies, it's rarely this good.