As I have done with previous books I have preached through (John, Philippians, Psalms, Micah, James, Daniel, Ruth, Galatians, just to name a few), here are my thoughts on Hebrews commentaries:
1. Best Hebrews Commentary: Peter O'Brien's Pillar New Testament Commentary on Hebrews.
2. Very Helpful: Stuart Olyott's I Wish Someone Would Explain Hebrews to Me! and Raymond Brown's The Message of Hebrews
3. Good Homeletical Commentary: Richard Phillips' Reformed Expository Commentary.
4. Decent, but not as helpful as the others: FF Bruce's NICNT and George Guthrie's NIV Application.
5. Classics: John Owen (abridged in one volume) and AW Pink.