When he was about to graduate from high school, he decided to become a singer. His debut single was called Bunkacha-Bushi, which was released in 1962.
He has many famous songs, including Kita no Sakaba and Yosaku. He is very popular in Japan partly due to his looks of a physical laborer, and he mostly sings the spirit of Japan's working class and rural laborer. He often appears on Kōhaku Uta Gassen, a TV program at the end of the year where many major Japanese singers gather to perform.
Although Enka is becoming less popular with the younger generation, he is still Japan's most famous singer. He does a lot of concerts overseas as well, and he is contributing a lot of work to the culture of Japanese music.
In addition to his singing career, Kitajima acted in the role of Tatsugorō on the television series Abarembo Shogun. During the quarter-century life of the series, he also sang its theme songs.