The ordinary man looking at a mountain is like an illiterate person confronted with a Greek manuscript.–Aleister Crowley Boasting in his Confessions, Aleister Crowley (1875–1947), with all the braggadocio of youth, claimed he was “white-hot on three points; climbing, poetry and Magick.” All these pursuits were to define his early career as a mountaineer, poet and magician. Given his immersion in the latter two, Crowley’s hitherto neglected mountaineering career has only recently excited a renewed interest by his various biographers. This presentation intends to put into context Aleister Crowley’s controversial mountaineering career particularly regarding his involvement in the first ever attempt to scale K2 (1902) and then Kangchenjunga (1905), the world’s second and third highest peaks. Having climbed throughout the British Isles and then the Alps, Crowley came under the wing of Oscar Eckenstein (1859–1921), his mountaineering superior.