Few could argue that the major border all humans cross demarcates Hamlet's “undiscovered country, from whose bourn/No traveller returns.” This paper considers Margaret Edson's play Wit, with its trenchant portrayal of the “transition, transformation, and consequent redefinition of the self” as its protagonist, a Donne scholar dying of cancer, experiences and comments on her passage from lucid observer to the outcome of her Do Not Resuscitate. Unsurprisingly, as the Baby Boom generation travels through its senior years, plays about dementia, decrepitude, caregiving, and dying have become a significant presence on the American stage. Most are by men; most depict helplessness, incontinence, pressures on middle-aged family members, and a certain dottiness in the elderly. Indeed, one such play—Colman Domingo's Dot—puns on the very word. (Other examples include Taylor Mac's Hir and Jordan Harrison's Marjorie Prime.) Edson's play is singular for its use a Brechtian techniques, allowing the protagonist both to engage our sympathy and to use wry wit and barbed editorializing to depict discovery as much as decline. In two recent articles, Elinor Fuchs argues on behalf of revisioning the depiction of age in drama, calling for a “theatre of estrangement thriv[ing] on a separation of dramatic elements” so as to allow a dialectic examination of the voyage towards death—especially with the element of dementia—to do more than fulfill a familiar (arguably too Aristotelian) narrative of maudlin descent. Fuchs makes an additional appearance here as more than theorist. She is the author of the memoir Making an Exit: A Mother-Daughter Drama with Alzheimer's, Machine Tools, and Laughter. My paper considers the possibilities (and limitations?) of genre as well as the application of what Fuchs names “estragement,” riffing on Brecht to invite a new optic on the representation of the approach to the undiscovered country.