This paper explores the trajectories of black manhood and fatherhood in modern and contemporary American literature and literary criticism and contemplates a possible space for “good” black fathers. As we investigate how earlier discourses and discussions on black manhood have been constructed, and have remained and developed, there certainly is a change or progress in reading and creating different types of representations of black men — without focusing too much on body and sexuality — in American literature and literary criticism, starting from a ragged image considered problematic, violent, dangerous, or bereft, and under institutionalized destitution. This denigration of the black male has intensified and solidified myths of the black family — a black matriarchal family that lacks a desirable father figure, consequently leading to the effeminized, castrated black masculine presence in their communities — but has come to be questioned, leading to a somewhat hopeful, positive, and even philosophical depiction by questioning the core of defining good and bad under the dire circumstances within which African American men find themselves. By scrutinizing innocuous, caregiving father figures dwelling at home in African American novels, this paper looks back at how literary criticism and literature itself have exercised creative power in order to give birth to the “good” black men, who were deemed nonexistent or insufficient before, through re-reading, re-tracing, and re-looking at black fathers/men in novels written by renowned literary figures from Richard Wright, Ralph Ellison, James Baldwin, and Toni Morrison to contemporary — and relatively young — authors such as Leonard Pitts Jr. and Bernice L. McFadden.