In 2018, Barbra Streisand released her 36th studio recording, Walls. The album's songs, a mixture of originals and covers, focus on the cruelty of President Donald Trump. In orchestrating and celebrating a particular set of positive feelings—love, hope, and longing—Walls, like much of Streisand's work, is deeply sentimental. Understanding our current political crises, Walls asserts, is more an act of sympathy than intellect; we must “feel the tears” that have been cried. Using Walls as the focus, this essay explores the ways Streisand's sentimentality has always been intertwined with her political activism. This fusion is not unique to Streisand, and my essay here is intended to show how deeply rooted the connection between sentimentality and politics has been in US American cultural history. From its development as an independent philosophical idea in the eighteenth century, through its nineteenth century popularization via women-authored novels, sentimentality has always had a political valence as well as a racialized character. I trace this sentimental–political aesthetic, what Jennifer Williamson, Jennifer Larson, and Ashley Reed call the “sentimental mode,” through two key recordings from the 1960s and 1970s: “People” and “Evergreen.” I then turn to Walls, which uses music to instruct listeners in the affective identification with the suffering of others. However, in its focus on racial others—such as immigrants from the global South—Walls also brings with it the problematic racial legacy of sentimental politics where genuine concern for the downtrodden was mixed with essentialist ideas of racial identity and hierarchy.