Scholars of modern Egypt have begun to reassess how they approach the 1960s, a decade of major transformations in the country typically tethered to the 1967 War. This work has shifted focus away from political dimensions and drawn on cultural productions like literature and cinema to study the period beyond a framework of trauma (Abou-El-Fadl 2019; El Saket 2023). Yet, scholarship largely continues to center local and regional (pan-Arab) solidarities of the decade, as well as Egypt’s relations with the US/Europe. There remains comparatively little on the ways that Egyptians asserted links in other directions, thus overlooking a more complex history of global flows. This paper investigates Egypt’s cultural connections with Japan during the 1960s. It discusses exchanges between these far ends of Asia through a case study of the late Egyptian artist Ragai Wanis (1938–2023). Wanis first visited Japan in 1962 on assignment with his employer Ruz al-Yusuf, the popular weekly. Enchanted by its “amazing blend of old and new,” he returned to Japan shortly after to study and work for five years in the mid-sixties. As I show, Wanis was part of a broader shift that prompted writers, actors, musicians, and many state officials to visit the distant nation. My analysis of this period draws on a range of sources—Wanis’ published memoirs, his paintings, and photographs—to uncover a vibrant period of transregional entanglements after mid-century, when new travel infrastructures and media brought the two countries closer than ever before. Ultimately, in examining figures like Wanis, this paper offers an alternative narrative for Egypt’s 1960s while highlighting how the field of cultural production can add new texture to our understanding of the Middle East.