The madrigal was the most important and most experimental musical genre of secular music in the late Renaissance Era. As unaccompanied vocal works, based on “elevated” poetry, madrigals took the Renaissance infatuation with “the word” to the next level. Through the cultivation of word painting, madrigalists illustrated and heightened the meaning of the words of their madrigals, often employing extremely venturesome harmonic progressions. Madrigals by Cipriano de Rore, Carlo Gesualdi, and Thomas Weelkes are examined in order to observe the progressive development of the genre from the mid- 16th century to the very early 17th.