While examining the sexual liberation movement that surrounded the American counterculture of the mid-twentieth century, numerous scholars have commented on the counterculture’s perpetuation of gendered stereotypes, constructs, and double binds. Few, however, have substantially linked the counterculture’s underlying sexism with its music. This paper explores how British and American musicians maintained, and, in some cases promoted, gender stereotypes and sexism by studying the rock and roll and folk music produced between 1964 and 1969. Through popular artists such as the Rolling Stones and the Grateful Dead, and through underground musicians such as Bert Sommer, this study uses the lyrics of the songs released during this five-year time frame to examine how the music of the 1960s counterculture portrayed its view and treatment of women. Moreover, this study assesses the accuracy of the rhetoric that has come to surround the counterculture movement of the 1960s that paints it in a light of equality, freedom, and progressiveness. By surveying and categorizing countercultural songs into four categories (possessive, objectifying, promoting abuse, and generally degrading/perpetuating stereotypes), this study contributes to a greater understanding of the sexism maintained by the counterculture of the 1960s and adds music as a new component to the existing discourse around the gender stereotypes, constructs, and double binds in the counterculture movement.