Raizō's position as a star had been secured. The Nemuri Kyoshirō series of films, which began in 1963 and are known as Sleepy Eyes of Death in the west, are considered to be the representative work of Raizō's later years. According to Tokuzō Tanaka, playing the part of the protagonist, Kyoshirō, was an extreme challenge for Raizō. Speaking of the first film in the series, Sappōchō, even Raizō himself said that "the characteristic 'hollowness' of Kyoshirō simply didn't come out at all" and deemed the film a failure. It wasn't until the fourth film, Joyōken, that Raizō succeeded in bringing the hollowness, dandyism and nihilism of the character to life. The actor Shintarō Katsu described Raizō's performance in the Nemuri Kyoshirō films, saying "When he was playing Kyoshirō he had a real animal magnetism about him, didn't he. Maybe you could say it came from this sense of the shadow of death hanging over him. It really is the face people make when they die, that expression." “When he’d walk by, Rai-chan would cut you with his face. Not with a sword, with his face,” he reminisced, “Rai-chan didn’t become Kyoshirō through his fight scenes or the delivery of his lines, he did it through his face; that’s my opinion, anyway.” Kazuo Ikehiro said, “without speaking, without any kind of facial expression, simply by the way he walked around as though he were carrying his past on his back” Akira Inoue, director of the seventh film in the series, Tajōken, said that there were other actors who played Kyoshirō, but none of them could compare to Raizō when it came to portraying Kyoshirō's soul. Raizō went on to hold the starring role in 12 films in the series, which represents a majority of the starring roles for which Raizō was cast. According to Kazuo Ikehiro, as Raizō's experience as an actor accumulated he began to desire to take a larger role in film creation through directing. Ikehiro advised Raizō to pursue the role of producer, rather than director, as he would then be able to make decisions about subject matter, scripts, and casting in addition to direction. In January 1968, Raizō said “I want to assemble a new dramatic production, the likes of which has never been seen before,” and began the process of establishing a new theater company called “Teatoro Kaburaya” at which he would take a producer role,