The Loser Takes All (2002)

Original title: Ο Χαμένος Τα Παίρνει Όλα

Man (Gianis Aggelakas), a mysterious man of the underworld, small time grifter and big time hard-man, who has an anarchic tendency to mumble and comment 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 kid, who is 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 five of them 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.