Today, 17 October 2021, marks 101 years since the birth of American actor Montgomery Clift (1920 – 1966). This talented actor was a four-times Academy Award-nominee and is known for such films as The Search (1948), From Here to Eternity (1953) and Judgement at Nuremberg (1961). He often played smooth-talking, melancholy and mysterious men who rebelled against the establishment. Despite the immensity of Clift’s talent and charisma, however, Hollywood never seemed to know what to think of him and he was often portrayed “a black sheep” of the cinema business, a perpetually tortured soul who privately fought many mental and physical battles. Though never openly gay or bisexual, Clift always had his private life under wraps and struggled to fit into the image that Hollywood wanted him to fit into: the image of the Golden Boy who is after money, financial success and women. Though now often overshadowed by, and even compared unfavourably to, such cinematic icons as James Dean and Marlon Brando, Montgomery Clift deserved and still deserves much more, especially since both of these actors looked up to Clift and was inspired by his image to forge theirs. Clift was one of the most talented American actors and, unfortunately, one of the most misunderstood ones, who valued the craft of acting above financial success or even critical/public opinion, who wanted desperately to retain his unassuming, independent and original inner core despite the environment that constantly wanted to mould him into something else, a Hollywood environment that favoured flashy displays of wealth, stereotypes and double-dealings. Clift’s story is as much a tale of one talented and intelligent actor following a tragic path as a story of Hollywood’s callousness and complacency.