The life of Alexander the Great was clouded in legend from his own lifetime, not least because Alexander himself curated his image with such care. Disentangling the truth is not an easy task, especially because our surviving narratives, including Plutarch's, all date from centuries later under the Roman empire. Plutarch's Life of Alexander is especially important for Alexander's early years, but for his later achievements too it often supplements or corrects our other accounts; it is also a considerable literary achievement, as Plutarch produces a memorable picture of a brilliant soldier, full of spirit and ambition, gradually coarsened by his own successes and his suspicions of his friends until his final months at Babylon in a court full of superstition, terror, and dread. Plutarch had to navigate his way through an unusually vast stock of material to produce this portrait. This commentary discusses those literary techniques in detail as well as providing a thorough investigation of the historical issues that Plutarch's narrative raises.