This is my smallest bookshelf, because as a homiletics PhD candidate I can't help but overthink this one. There are a lot of great preaching books out there--here are just a few of the ones that I can recommend without reservations.
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How Shall They Preach
Gardner Taylor, one of the great North American preachers of the 20th c., offers some essential reflections on what it means to preach and be a preacher. His sobering insight helps foster fitting humility for ministers of God's Word.
Preaching with Variety
Jeff Arthurs has been an irreplacable mentor to me, and I find this short book offers helpful insight on one of Arthurs' own strengths: Allowing the genre of a Biblical text to shape the sermon. It's a good book to read cover to cover and a great reference book for sermon writing.
Haddon Robinson's text is one of the most influential preaching primers today, and sometimes separates those who consider it a second Bible from those who consider it woefully outdated. I wouldn't call it either one of those things, but it would still be the book I would choose if someone asked for a single book to help with preaching. Sure, we should perhaps do more than Robinson addresses in the book, but not less. Recognizing, crafting, and communicating a clear, compelling big idea can help us all serve those with whom we're speaking.