Most guidance for preaching Christ from the Old Testament focuses on narratives or prophetic books. This paper focuses on the specific challenges of preaching Christ from the proverbial literature of the Old Testament. It shows how to compare and contrast biblical wisdom with cultural wisdom (in both the wider culture and the Christian subculture). Since wisdom is often indirect law, it can function as other biblical law does: convicting us of sin and driving us to Christ, who is the wisdom of God and has thus lived with perfect wisdom in our place. It can also exhibit the third use of the law, which is as a guide to wise Christian behavior.