The recent high school graduate wrote me,
“Denny, I know your academic training was in history and that you remain deeply interested in it. I was wondering if you could tell me who the best historians are for me to start reading?”
My reply --
You raise an interesting question and it's been kinda' fun for me to think about. Of course, the first issue is selecting the type of history. The fellows dealing with the history of philosophy or ancient Rome or World War II are, most likely, going to be different. Naturally then, my favorites will be guys who cover the areas of history I'm most interested in.
Another thing I should mention is that some of my very favorite books of history were not written by professional historians at all. A conservative speechwriter wrote my favorite history of the Reagan administration -- Peggy Noonan. A soldier wrote my favorite history of the American Civil War -- Ulysses Grant. And my favorite histories of the U.S. space program were written by two scientists and a novelist -- Chris Kraft, Gene Kranz, and Tom Wolfe.
Keep in mind too that autobiographies are history and they are rarely written by professional historians. Also, novelists and playwrights frequently serve as excellent chroniclers of history. I especially appreciate in this category Fyodor Dostoevsky, Charles Dickens, William Shakespeare (aka Edward de Vere), Sir Walter Scott, Leo Tolstoy, Alexander Dumas, Victor Hugo, Jane Austen, Evelyn Waugh, Boris Pasternak, the Brontes, and Alexander Solzhenitsyn.
But enough traipsing around your question. If you can keep all of these things in mind, I will mention a few professional historians that have indeed made the top rank for my interests and purposes. I'm quite sure I'll leave a couple out but, without classifying them as to time or subject, here's some names: Shelby Foote, Samuel Eliot Morison, Walter Lord, John Toland, David McCullough, Antonia Fraser, Laura Hillenbrand, Roland Bainton, Winston Churchill, Paul Johnson, Stephen Ambrose, Bruce Catton, and William Prescott.
By the way, among these my absolute favorites are Foote, Morison, Lord, and Hillenbrand.