Kitao Masayoshi was born in Edo in 1764. Initially he was the pupil of Kitao Shigemasa, later under Kano Yosen'in Korenobu. He worked as a ukiyo-e artist under the name Kitao Masayoshi, then became official painter to the daimyo of Tsuyama and worked in the Kano style using the name Kuwagata Keisai. During his time as a ukiyo-e artist, Kitao Masayoshi produced mainly novelette illustrations. Once he became a painter to the daimyo of Tsuyama, he switched mainly to paintings and printed albums. He produced many instructional manuals on how to paint in 'abbreviated style' (ryakuga-shiki).

Kitao Masayoshi, also goes by the following names:

Kitao Masayoshi (before, art name); Kuwagata Keisai (鍬形恵斎); Keisai Masayoshi; Sanko (art name); Akabane (family name); Tsugusane (na); Tsuguzane (na, alternative reading); Shoshin (na); Shikei (azana); Sanjiro (common name); Mugino Orochimaro (kyoka-go); Kisho Tengo (gesaku-go)