Last Friday I recommended an extremely readable but textually faithful overview of Ecclesiastes by Douglas Wilson called Joy at the End of the Tether. If you want a solid, engaging, and at many points hilarious commentary on “the inscrutable wisdom of Ecclesiastes,” Wilson is your guy.
But for those teaching or preaching through Ecclesiastes, you are going to want to supplement your study of the Biblical text with more than just Wilson’s book. The first commentary I read on Ecclesiastes, coincidentally referenced by Wilson in his endnotes, was Walter Kaiser’s Ecclesiastes: Total Life from the “Everyman’s Bible Commentary” series. Originally written in 1979, I would tag Kaiser’s work as a must-read if you are looking to teach through this biblical book. Walt Kaiser is one of the preeminent Old Testament scholars of the last generation, and I would heartily recommend all of his work. I had the privilege of getting to know him personally when I was a student at Gordon-Conwell in the early 2000’s. He was the President of the seminary at the time, and still taught classes on a semi-regular basis. He retired from that post the year I graduated (2006).
Kaiser’s commentary, while a more scholastic work than Wilson’s, is still readable and accessible. It is outlined like a basic commentary, with introductory thoughts followed by passage breakdowns. What I appreciate about Kaiser is that he is theologically conservative, biblically sound, and faithfully applicable. He argues that many scholars miss the boat on Ecclesiastes, calling it a book of pessimism, when in reality “the mood of Ecclesiastes is one of delight, with the prospect of living and enjoying all the goods of life once man has come to fear God and keep His commandments.”
Kaiser holds the traditional opinion that Solomon was the author of Ecclesiastes. Unfortunately, a range of critical scholarship in the last couple centuries has not only questioned this traditional assumption, but sought to denounce it. Kaiser lays out the clear reasons for holding to Solomonic authorship, really empowering those of us who want to stick to the position held by all Jews and Christians alike for over two and a half thousand years (until about the 16th century).
What you’ll get out of this commentary is sound exegesis of the book, clear explanation of any linguistic difficulties (Kaiser is an expert in the Hebrew language), and applicable references to how you can get about the business of preaching Ecclesiastes. Have at it, my friend.
 p. 42.