Long-associated with “insurgent” or alt.country and what is now “Americana,” Chicago’s Bloodshot Records’ first release (For a Life of Sin: A Compilation of Insurgent Chicago Country, 1994) was a compilation album featuring local punk and indie bands performing various styles of country music. The label’s ongoing use of compilation and tribute albums was not only commercial but also strategic in maintaining a connection to the label’s roots in the Chicago punk and underground rock scene, reinforcing its adherence to a DIY (do-it-yourself) aesthetic and highlighting small-scale production and consumption practices. This chapter argues that Bloodshot’s tribute albums are significant for the layers of meaning they contributed to a label’s branding and identity by historicizing and legitimating the record label’s early country offerings while offering an argument for the importance of the independent record label and non-mainstream musical practices in the twenty-first century.