Dale Ralph Davis is either the best Old Testament preacher you’ve never heard of or he probably features in your list of the best ones that you have heard of.
This post at the Gospel Coalition points to some resources by Davis that are hosted on at the GC website. You can also find audio recordings of his sermons here.
There’s a short interview, conducted by Collin Hansen. Here’s a couple of questions which demonstrate Davis’ insight, and also the fact that he will make you laugh more than any other serious OT expositor that I know.

What is the greatest challenge for preachers and teachers when it comes to preaching the gospel from Old Testament narratives?
I might say that the “challenge” consists in a “caution”—don’t be trying to “jump start” the OT passage to Jesus. That sounds impious. But I get the sense that sometimes men can be so driven by their christocentric dogma that they don’t really hear the OT passage on its own terms or try to lay bare its own theological intent. They are too busy trying to find clues and handles (typological or otherwise) by which they can get to Jesus. I can recall a case where an interpreter’s eye has been so focused on how a passage points to Christ that he completely omitted the major theological issue the passage raised.

Can you point to helpful commentaries and other resources for preaching Christ from the OT?
There are gobs of books that deal with preaching Christ from the OT. I find I get more use from commentaries because I am usually dealing with particular texts of OT narrative. And what one prefers in commentaries is—like one’s toothbrush—very personal, I suppose. I prefer commentaries that focus on the meaning of the text (rather than go through 200 years of scholarly guesswork on how the text came together) and/or that focus on the theological intent of the text. But I shall not give any list. It all depends on the biblical book I’m working in.

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