Generosity explores the issue of homelessness through five main characters. Just how close is anyone to homelessness? David has a good job, friends and a nice apartment. After his mother takes ill and he is wrongly accused of embezzlement, he loses his job and finds himself out on the streets. Chloe has run away from an abusive step-father to live with friends, but after they kick her out she does whatever she can to keep alive. Sam has been homeless for years and takes in David and Chloe, and mentors them in the how to's of living on the street. Charlotte is a TV news reporter who wants to do good and help people while advancing her career. Bob is a unforgiving, greedy corporate president who hates the homeless and is not afraid to let them know it. As their stories intertwine, the lines between who is begging, who is dependent and who is good start to blur, until all hell breaks loose.