The goal of this study is to relate blues characteristics as they appear in the playing of Johnny Hodges, Charlie Parker, and Ornette Coleman, to blues lyrics, Signifying, the artists’ life experiences, and to the ancient cultural icon Esu-Elegbara. This study reviews the theory of Signifying, discusses existing literature on blues Signifying, and investigates select biographical information of each player. In addition, the study presents and analyzes transcriptions of jazz improvisations for each artist and reveals and investigates their blues characteristics. The study then contextualizes discovered blues characteristics in terms of blues lyrics (and consequently their melodies), the meaning of these lyrics, and later their respective artist’s life experiences. Findings show that each artist has personal similarities to the Yoruban cultural figure Esu-Elegbara. These similarities assist in revealing the Signifying nature of the blues characteristics in the case studies’ improvisations.