This article intervenes in queer theoretical approaches to nostalgia through an analysis of the 2004 film Brother to Brother, which presents a fictionalized account of the final months of the life of Harlem Renaissance artist and writer Richard Bruce Nugent. One reading of this film would insist that it merely substantiates the claims made in other contexts by a number of queer theorists that nostalgia is bad history and worse theory—uncomplicated, weak, and sentimental. However, this article offers an alternate reading, which reaches beyond accusations of sentimentality and historical inaccuracy to insist that the nostalgia ultimately prevailing in Brother to Brother functions as an anti-racist and anti-homophobic rejoinder to paranoia about the so-called “down-low” phenomenon, which obsessed the media and the public during the early 2000s. In Brother to Brother, the central problem for Nugent’s protégé, a young, black, gay artist named Perry, is negotiating his membership in two contested identity categories often understood to be in tension. His intersectional identity makes impossible the kinds of community he desires. In contrast, Nugent’s 1920s moment, depicted in black and white flashbacks, makes available to the young Nugent exactly those pleasures, communities, and opportunities inaccessible to Perry. This article argues that the film therefore negotiates black gay identity at the turn of the millennium—an identity category under siege from a number of directions—in and through nostalgia for the gay Harlem Renaissance.