Anne of Green Gables is one of the most popular works in the World Masterpiece Theater series, both in Japan and in the English-speaking sphere. According to many of those who have seen it, it may even qualify for the title of best anime of all time. It also represents a historical turning point: it is the first entry in the time slot that was now officially called “World Masterpiece Theater”, instead of “Calpis Children’s Theater” (1975-1977) or “Calpis Family Theater” (1978). And yet, it is perhaps the most imperfect among Isao Takahata’s three shows for Zuiyo Video/Nippon Animation, and by far one of the most difficult productions that the director, studio and all the artists involved had known. This latter, darker aspect of Anne appears to be at best underdiscussed, or at worst completely unknown, in English-speaking circles. While providing a detailed commentary and analysis of the show as well as its place in anime history and Isao Takahata’s career, this article also aims to raise awareness and shed light on those somber moments.