The majority of the court documentary paintings of the Joseon dynasty are commemorative paintings of court rites presided over by the king. Among these, there are extant today thirteen paintings pertaining to the Crown Prince, all produced between the sixteenth and nineteenth centuries. Four of these were commissioned by the Sigang-won, Tutorial Office for the Crown Prince. They include an eight-panel commemorative folding screen illustrating the investiture ceremony to appoint the Heir Apparent or Crown Prince Munhyo (1782-1786); an album of six scenes created to commemorate Crown Prince Hyomyeong (1809-1830)'s commencement of learning at the Seonggyun-gwan; an album of five scenes illustrating the rites pertaining to the Crown Prince's hoegang (會講: review session); and a thirteen-page painting album with no inscription or annotation referring to its subject matter, but comparative analysis indicates that it is the Crown Prince's coming-of-age ceremony granting formal admission into adulthood. The remaining paintings are nine albums produced in the late eighteenth and nineteenth century illustrating various court ceremonies related to the Crown Prince. These painting albums are distinctly different from the folding screens that were then the favored form of documentary paintings. Their instructional nature reflects the special relationship between the Crown Prince and the officials of the Sigang-won, and highlights the initiative and special consideration undertaken by the latter for the education of the former. They also underline the political background during the reigns of Kings, Jeongjo, Sunjo, and Gojong with respect to policies introduced to strengthen the monarchy and the status of the Sigang-won. In conclusion, the Joseon documentary paintings that concern the Crown Prince are closely related with the political currents of the time such as the political reinforcement of the monarchy and of the Sigang-won. Such political links most likely served as an important catalyst in the production of documentary paintings. There is a need to analyze further from political and social perspectives the dynamics between the political setting and the actual participants involved in the production of these paintings, whose names are sometimes listed in full in the works.