Makovsky's work was defined by a perpetual humor as well as blatant irony and scorn. During the seventies his paintings dealt primarily with small-town folk. His pictures, "The Grape-juice Seller" (1879), "Fruit-Preserving" (1876) and "The Congratulator" (1878) depict various scenes where the mood is finely conceived and almost laughter-inducing. Other works of his, such as "The Benefactor" (1874) and "The Convict" (1878) are profoundly socially conscious. In them, Makovsky either criticizes the false sympathy of the aristocracy towards the poor, or draws attention to the oppression and persecution by the tsarist gendarmerie. In 1878, he became an academician.

In the eighties, during the time of Russian "democratic" painting, Makovsky produced some of his most valued works. In 1882, he was made professor at the Moscow Art School after the death of Vasili Perov. Some of Makovsky's greatest works of this period include "In the Ante-room of the Court of Conciliation" (1880), "The Released Prisoner" (1882), and "The Collapse of the Bank" (1881). From the end of the 1880s, Makovsky began to produce more gloomy works. Quintessential works of this period include "You Shall Not Go" (1892), and "On the Boulevard" (1888).

In 1894, Makovsky became Rector of the Preparatory school of the Academy of Art. After the First Russian Revolution, he painted "January 9, 1905, on Vasilyev Island" in which he depicts the armed police firing at defenseless people. In another painting "The Sacrifices on the Khodyn Field" in which a thousand people lost their lives during the coronation ceremony in 1896 of Nicholas II, he again stood uncompromisingly on the side of the oppressed people.