A mix of documentary and scripted footage on the Bowery, New York City's skid row. Against a backdrop of men (and a few women) drinking in bars, talking and arguing, and sleeping on sidewalks, we have the story of Ray. He is younger and more vigorous than most on the Bowery. He arrives in Manhattan with a suitcase and a little money in his pocket. On his first night, he drinks himself into a stupor, falls asleep on the sidewalk, and is robbed of his suitcase. Over the next two days, we follow both Ray and the thief, who befriends him. Is there any hope Ray can get out of town and restart a life of work and sobriety, or is he stuck on the Bowery? Can the good thief help?

Dave Chappelle presents a Brooklyn neighborhood with its very own once-in-a-lifetime free block party. In addition to Chappelle, the roster of artists includes Kanye West, Mos Def, Talib Kweli, Common, Dead Prez, Erykah Badu, Jill Scott, the Roots, Cody ChesnuTT, Big Daddy Kane, and - reunited for their first performance in over seven years - the Fugees. Includes private rehearsals footage and Chappelle in the small Ohio town he calls home, where he wanders through town handing out golden tickets to invite several dozen citizens to join the party, providing transportation and lodging for their visit to Brooklyn. Ohio's Central State University marching band makes the trip and kicks off the festivities at the intersection of Quincy and Downing Streets. A diverse crowd and Chappelle's freestyle wit guides them (and us) through a celebration of music and comedy, history and community.