As an Old Testament professor, I struggled with how to teach the Book of Proverbs and the genre of Wisdom Literature in general to my seminary students. As I read and re-read Proverbs, however, I saw it contained many character stereotypes. It is a very contemporary book, for it shows the qualities that contribute to success or failure in life over a long period. The characters in Proverbs, exaggerated as part of the genre, make important choices about how to live. I grouped verses about the types of people one sees daily in life's marketplace and wrote a vaudevillian-style play called "Life's Choices: A Play Based on Eight Characters in Proverbs." The actors, all university students, wear nametags. The set is minimal: ladders, tables, chairs. The time is morning on Main Street in the local university town. Simple Youth, a First Year student and the play's hero, faces many choices, On Main Street he meets Sluggard, who nuzzles a teddy bear and tries to sleep all day; Drunkard, who totes a big wine bottle and looks for a fight; Satisfied Husband, a magistrate who constantly talks about his noble wife, the Proverbs 31 woman; Adulteress, a lonely woman looking for men; Gossip, who delights in breaking up friendships; Lady Folly, who likes the easy way; and Lady Wisdom, who invites everybody to her banquet. Which lifestyle will Simple Youth choose? The play, containing musical interludes and dances, was so well received that it became a video and thereby a permanent teaching tool for various Old Testament classes and modules. It clearly integrates visual art and the biblical text in a modern fashion. This paper presents excerpts from the play as a discussion tool for teaching Proverbs.