Men Without Jobs (2004)

Compulsive gambler Oz lives in a rent-controlled apartment in Brooklyn, with his roommate, Ivy-League dropout Ish. Crippled by an unspoken fear of failure, the serial underachievers whittle the hours away playing video games and discussing plans for a band that has yet to leave the realm of the hypothetical. But after they meet graffiti artist Veronica, who challenges them to take action, Oz and Ish must examine themselves for the first time.