Scripture contains extensive genealogical records that were precisely documented and preserved throughout countless generations. Collectively, they form a highly valued written record in the ancient biblical world, documenting the ancestry of individuals, families, clans, the tribes of the nation of Israel, and even Gentile foreigners who were brought into the covenant family of faith (i.e., Jews and Gentiles who came to hold “the faith of Abraham . . . the father of us all”; Romans 4:16). Since genealogies often exhibit a high degree of complexity, they can have practical challenges for exegetical study. This is especially true for understanding the genealogies of Jesus the Messiah as presented by the Gospel writers in Matthew 1:1-17 and Luke 3:23-38. This paper will discuss the genealogical patterns and the literary substructure of both compositions. It will explicate the (biological and legal) patrilineal descent of Jesus from Abraham, David, and his earthly father (Joseph) in the Matthean account and discuss the longest linear genealogy found in Scripture (a list of seventy-seven names) in the Lukan account which traces the ancestry of Jesus in father-to-son succession back to Adam. Also discussed will be Matthew’s deliberate inclusion of five ‘questionable’ women in the Messiah’s ancestry: Tamar, Rahab, Ruth, Bathsheba (“the wife of Uriah”), and Mary the mother of Jesus.