Most "100 best military history books" lists give you a wall of titles and zero advice on where to begin. Two short reading orders I think are more useful, both built around John Keegan as the anchor for the modern field.
Military history, by era: start with John Keegan's The Face of Battle, which rebuilds Agincourt, Waterloo, and the Somme from the soldier's view. Then move chronologically: Sun Tzu's Art of War and Hanson's A War Like No Other for antiquity, Chandler's Campaigns of Napoleon and McPherson's Battle Cry of Freedom for the nineteenth century, Tuchman's The Guns of August and Keegan's First World War for WWI, then Beevor Stalingrad + Sledge With the Old Breed for WWII, and Bowden Black Hawk Down + Halberstam Best and the Brightest for the wars after 1945.
Napoleonic Wars specifically: the campaigns are huge but most readers know only Waterloo. A campaign-by-campaign reading order works better than chronology. Chandler Campaigns of Napoleon for the spine, Zamoyski Moscow 1812 + Lieven Russia Against Napoleon for the Russian disaster, Esdaile Peninsular War for Spain, Cornwell Waterloo + Clayton Waterloo for the end, and Rodger Command of the Ocean + Nicolson Trafalgar for the naval side most lists ignore.
For the full ranked versions with FAQ schema, I keep the two reading guides on Skriuwer: the best military history books and the best books about the Napoleonic Wars. The Napoleonic page in particular fills a gap, since most general military history lists treat 1803-1815 as a single Waterloo entry rather than a global conflict.
If you only have time for two books across both reading orders: Keegan Face of Battle and Chandler Campaigns of Napoleon.
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