In 2018, Lauren Alaina released her single “Ladies in the ’90s,” which takes a nostalgic look at her childhood through cleverly chosen lyrics from chart-topping songs of the 1990s. “Ladies in the ’90s” references women—and only women—from country music, as well as pop, rock, and R&B. The song establishes Lauren Alaina’s broad musical lineage and evokes nostalgia for an earlier decade. This chapter explores the performative and affective use of nostalgia and lineage in country music. A close reading of “Ladies in the ’90s” reveals how the generation of country artists coming of age in the second decade of the twenty-first century are redefining and expanding the stylistic, cultural, and even racial boundaries of the genre through the nostalgic tropes that have been used for decades in country music. In so doing, artists like Lauren Alaina are challenging the industry and carving out new musical and narrative spaces.