Darwin was amongst the first to argue for the existence of parallels between birdsong and human language. In his book, The Descent of Man, he expresses that "the sounds uttered by birds offer in several respects the nearest analog to language." Was he right? A robust body of evidence accrued over 100 years of prolific research in birdsong endorses the claim. This dissertation is a collection of my modest efforts towards furthering this research program.In Chapter 1, I explore the evolutionary genomics of the Bengalese finch, a tame songbird frequently found in pet shops and equally popular among scientists studying learned vocal behaviors. Using whole-genome sequencing and population genomic approaches, I identify selection signals that differ between Bengalese finches and their wild munia ancestors. Findings from this study suggest that, as with mammalian domesticates, the domestication of the Bengalese finch involved a shift in selective regime, capable of altering brain circuits favoring the dynamic modulation of motivation and reward sensitivity over overall augmented aggression and stress responses. Several lines of evidence demonstrate Bengalese finches have evolved more complex vocal abilities than their wild munia ancestors: adult Bengalese finches’ song retains a greater degree of variability in the ordering of vocal elements; Bengalese finches exposed to multiple tutors compose their songs from a combination of excerpts from the different tutor’s songs, in contrast to their wild ancestors, who latch onto and copy the song of only one tutor; moreover, in cross-fostering experiments, Bengalese finches can learn a munia foster parent’s song more efficiently than munias learn their Bengalese finches foster parent’s song. In Chapter 2, I track the Bengalese finches clues into their complex abilities in vocal learning, practice, and performance. To do so, I assess gene expression patterns in song-dedicated versus more generalist brain regions of juvenile Bengalese finches actively engaged in song learning via imitation and adult individuals past this sensorimotor learning phase, and primarily engaged in song maintenance and performance to females. Results from this study uncover co-regulatory patterns involving genes essential to motivation and reward. These patterns are developmentally and behaviorally regulated in the songbird brain, and likely contribute to motor learning, practice, and performance. In Chapter 3, I take an evo-devo stance to the study of vocal learning, and examine evidence that developmental timing, though not sufficient, may have been key to the evolution of complex vocal production learning. I point out how a sort of change in evolutionary regime common to domestication practices may bring about delayed developmental trajectories; and discuss its effects on brain circuits for motivation and reward sensitivity, as they relate to vocal learning