The Wackness (2008)

New York City, 1994: a city pulsing with hip hop, a city whose new mayor, Rudy Giuliani, is using controversial methods to address homelessness and crime. Much like the city, Luke and Dr. Squiresare at a crossroads: Luke considers himself semi-suicidal, bemoaning his high school social status and the fact that his family is on the verge of eviction; Dr. Squires and his rehab-addicted wife can barely tolerate each other. Together, Luke and Squires agree to help each other find happiness.