The Loser Takes All(2002)

The Loser Takes All follows Man, a cynical small-time grifter and hardened underworld figure who narrates his contempt for society, police, and the criminal world with sardonic commentary. Alongside his beloved bird Bellafonte, he assembles an unlikely crew: a young songwriter, a prostitute saving to open a bookstore, an alcoholic woman haunted by her mother's death, and his estranged ex-girlfriend who tends bar. When the five get entangled in a dangerous scheme involving corrupt media, mobsters, politicians, and cops, their only hope is escape. Dreaming of Caribbean freedom, this ragtag group must navigate the city's criminal underworld to survive and reach paradise before their enemies catch up.