Generosity is an in depth look at the issue of homelessness. Through five main characters, the film explores five very different perspectives and asks the viewer to "just how close is anyone to homelessness?" David is a straight-laced fellow who is successful at his job, has many friends and material wealth. After his mother takes ill and he is wrongly accused of embezzlement, his life quickly unravels and he finds himself out on the streets. Chloe is a tortured but spirited teenager who has run away from home. However, friends on the street do not prove reliable and she finds she must resort to the previously unimaginable in order to survive. Sam is charismatic, caring and anti-establishment. Having been homeless for many years, he offers respite to both David and Chloe, and mentors them in the ways of the street. Charlotte is an exhaustively optimistic TV news reporter who will go to any ends to help others and her career. Bob represents all that is wrong with corporate machinery.