The setting for "The Shadow Box" is three cottages on the grounds of a large hospital. Here, three tales unfold, at first serially, and then towards the end of each of the play’s two acts, simultaneously. Each tale features a person who is dying. Each person is surrounded by loved ones. All are trying to face and make sense of death.

The first family we meet is the most conventional. Joe, a working class husband and father, is joined at the cottage by his wife Maggie, who, in denial of Joe’s impending death is afraid to enter the cottage. Their son, Stephen, age 14, has not yet been told of his father’s terminal condition. The second family consists of Brian, who is brutally forthright about his demise; Mark, his doting lover; and Beverly, Brian’s wild ex-wife who comes to visit them. The third family is a feisty, blind, and wheelchair-bound mother, Felicity, and her dutiful daughter, Agnes. An off-stage character, "the interviewer," pops in and out of the scenes, offering insight into the various characters through questioning.