Ivan the Terrible and His Son Ivan on 16 November 1581 is a painting by Russian realist artist Ilya Repin made between 1883 and 1885. It depicts the grief-stricken Russian tsar Ivan the Terrible cradling his dying son, the Tsarevich Ivan Ivanovich, shortly after the elder Ivan had dealt a fatal blow to his son's head in a fit of anger. The painting portrays the anguish and remorse on the face of the elder Ivan and the shock and heartbreak of the dying Tsarevich, shedding a tear at the unexpected betrayal and shock of having been killed by his father's hands.

Ilya Yefimovich Repin was a Ukrainian-born Russian painter. He became one of the most renowned artists in Russia in the 19th century. His major works include Barge Haulers on the Volga (1873), Religious Procession in Kursk Province (1880–1883), Ivan the Terrible and His Son Ivan (1885); and Reply of the Zaporozhian Cossacks (1880–1891). He is also known for the revealing portraits he made of the leading Russian literary and artistic figures of his time, including Mikhail Glinka, Modest Mussorgsky, Pavel Tretyakov, and especially Leo Tolstoy, with whom he had a long friendship.