Born to an artist father, Vladimir Egorovic Makovskij entered the Moscow School of Painting, Sculpture, and Architecture in 1861, where he studied with E. Sorokine (1821-1892) and S. Zarianko (1818-1870) until 1866. In 1872, Makovskij made the most important professional decision of his life: he joined the Peredvizhniki (the Itinerants or the Wanderers), an artists' society that organized traveling exhibitions of their art. The Itinerants had founded their organization, the Society for Circulating Art Exhibitions, in St. Petersburg just two years earlier as a venue for contemporary artists to show their work without the constraints and prejudices of the official academic juries. In 1872, they moved their home base to Moscow, where Makovskij lived. In some ways, the Itinerants looked forward to the more radical efforts of the French impressionists, who formed their exhibiting society in 1874. Both wished to expand the opportunities for young, contemporary artists to exhibit their work and reach a wider audience, and the impressionists circumvented the need for art dealers and galleries, acting as their own sales representatives.

Although the Itinerants did not enforce a particular style or subject matter, many of their members, Makovskij included, came to share similar national subjects, socialist ideals, and a realist mode. In his early career, Makovskij generally produced small genre paintings of contemporary morals and manners, but by the late 1870s, he shifted to larger canvases portraying less fortunate, working-class Russians. Even though one of his clearly anti-establishment pictures, After the Catastrophe, was censored, Makovskij painted other politically challenging themes (Evening Party, 1875-97, Tretyakov Gallery, Moscow, and Interrogation of the Female Revolutionary, 1904, Central Museum of the Revolution, Moscow). For the most part, however, he focused on representing everyday inequalities to call for necessary sociopolitical change. To emphasize the actuality of these scenes, Makovskij used a realist style of unidealized forms, carefully detailed, undecorative settings, and a subdued, often dull palette. This subject matter and style conflicted with the aesthetic aims of the state-supported art academies that promoted idealized history painting and decorative monuments glorifying the official policies.

By the 1880s, liberal critics saw little difference between the works by academic artists and those by the Itinerants. The Russian arts administration changed its position toward the independent artists' association; instead of persecuting them, officials successfully recruited many of these artists, including Ilya Efimovic Repin (1844-1930), Ivan Ivanovitch Shishkin (1831-1898), and Makovskij, to return to the art institutions that they had attended and disliked for their rigid teaching. Makovskij taught from 1882 to 1894 at the Moscow school where he had studied, then took a position teaching genre painting at the St. Petersburg art academy, 1894-1916.

In addition to the Itinerants' traveling exhibitions, Makovskij participated in foreign art shows, such as the 1878 and 1900 Universal Expositions in Paris. Like many of the Itinerants, he benefited from the generous patronage of the Moscow art collector and museum founder Paul Tretyakov who, by 1878, owned Makovskij's Utile dulci and La bienfaitrice. His work is often confused with that of his older brother Constantin Yegorovic Makovskij (1839-1915).