Recently, there has been an increased effort to unravel selective factors behind female song evolution in songbirds. Female birds which produce songs may sing either solo or in duets; although the two vocal performances likely evolved through different selection forces and mechanisms, the majority of large-scale studies to date have focused only on duetting or female song in general (pooling female solo song and duetting into a single category). Hence, here we estimate the effect of behavioral life-history traits (territoriality, social bonds, cooperative breeding) and environmental productivity on the occurrence of female solo song and duetting separately in songbirds of South Africa and Lesotho. The focal region is characterized by subtropical/tropical climate, clear spatial environmental productivity gradient, and detailed knowledge on avian species distribution and behavioral life-history traits. Phylogenetically informed comparative analyses revealed that species where females produce only solo songs exhibited higher levels of territoriality than species with non-singing females (in an univariable model) but, simultaneously, lower levels than duetting species. Although both species with female solo song and duetting establish mainly long-term social bonds, the former defend their territories seasonally while the latter exhibit mainly year-round territoriality. Cooperative breeding and environmental productivity was not associated with the distribution of female solo song and duetting in any model. Our results indicate that when exploring female song ecology and evolution, female solo song and duetting are likely to be distinct song categories associated with different levels of territoriality.