The Loser Takes All (2002)

A mysterious man, small-time grifter and big time hard-man has an anarchic tendency to riff on the system, society, police, the underworld itself and other things, along with his beloved bird, Bellafonte, meets up with an odd posse consisting of a young songwriter, a prostitute who gathers money in order to open a bookstore, an alcoholic girl haunted by the relationship with her dead mother, and the grudgey bar-woman-ex-girlfriend. The quintet get caught up in a scheme involving the media, the mob, politicians and the police. And they definitely want to get the hell out of the city, probably to some Caribbean paradise.