Ross McElwee sets out to make a documentary about the lingering effects of General Sherman's march of destruction through the South during the Civil War, but is continually sidetracked by women who come and go in his life, his recurring dreams of nuclear holocaust, and Burt Reynolds.

After documentarian Ross McElwee gets married, a series of misfortunes follow: his grandmother dies, his wife miscarries, and then his father dies less than a week later. Shaken by the sudden string of deaths, McElwee becomes depressed. After spending time with his friend and former high school poetry teacher, Charlene, he goes to meet his brother, a doctor. In a series of interviews, McElwee contemplates his morbid preoccupation with death and tries to figure out how to shake it off.

Filmmaker Ross McElwee trails characters whose stories have been fodder for television news and takes their tales of loss and longing further than the requisite sound bite. In the process, he examines how the medium works and exposes its limitations.

In Charleen, documentarian Ross McElwee looks at the life of a North Carolina poet and teacher who acts as a muse to a motley crew of artists and musicians.

Ross McElwee travels through the North Carolina tobacco belt in search of the ancient southern traditions associated with tobacco growing and use, while comparing his filmmaking to commercial cinema, represented by Bright Leaf, a melodrama directed by Michael Curtiz in 1950, starring Gary Cooper, apparently based on the life of his great-grandfather.