The singer faces the difficult task of learning not only music, but also the song’s lyrics. For the classically trained singer, a common way to begin learning a piece is to isolate the music from the text by singing the music with only a single syllable. When the lyrics are reinserted, the challenge for the singer is to connect the words to the music’s melody in a sophisticated and expressive manner. The ultimate goal is to bridge the gap between the music and the meaning of the lyrics. The purpose of this paper is to investigate the relationships between the music and text in vocal repertory from 1600 until 1950 through the analysis of seven songs. This paper presents observations about music-text relationships that are directly applicable to enhancing the performance of these works.