When Sakurai was in his sophomore year of college, a group called the "Sun Valley Swing Band" asked him to be a pinch hitter, and after that, he officially joined and started working as a jazz pianist. After leaving college, he moved into various bands. In 1952, Toshiko Akiyoshi went to the United States and participated in the Gay Stars, where the pianist was absent, and Sakurai take over the group for her. After that, he formed a trio with Yasumitsu Suzuki and Akira Fukuhara, but at the invitation of Frankie Sakai, he joined the jazz band "Frankie Sakai and City Slickers". At this time, he met Kei Tani, who was a member at the time, as well as Hitoshi Ueki. After leaving the City Slickers a year later, he joined Toriro Miki's Joke Studio and taught singing and composition.