This article considers the precarious place of sentimentality in the contemporary historical moment. In light of the algorithmicization of everyday life, the possibility to make claims of fundamental connection—especially motivated by liberatory politics—has been imperiled. Building on Lauren Berlant’s analysis of sentimentality in American politics, I consider the present stalemate. I analyze a case study of two musicians—Joan Baez and Bob Dylan—by comparing two performances in Washington, D.C.: the 1963 March on Washington and a 2010 concert at the Obama White House honoring the former event. Seen comparatively, the political vulnerabilities of sentimentality come clear. And yet, in the case of Baez, we see also the potential of sentimentality—especially in the algorithmic present—to be used as productive political tactic toward collective reimaginations of the popular.