Tropinin was born to a family of serves of Count Anton Minnich in the Novgorod gubernia (province), but later was transferred into the ownership of Count Irakly Morkov who took the young man to St.-Petersburg. Tropinin was had been fond of drawing since his childhood and while studying the trade of confectioner in the capital, he started attending free classes at the Imperial Academy of Arts. Sometime later, Morkov sent Tropinin to his estate in Ukraine where the artist served as a confectioner and a lackey [a home servant of a lower rank-tr.], and in his spare time he continued painting: he painted frescoes for the local church, copied paintings by famous masters and created his own works, mainly portraits of Little Russian peasants. The artist was granted freedom from serfdom only at the age of 47 and went to St. Petersburg where he participated in a painting contest following which the Imperial Academy of Arts granted him the title of appointed Academician.

One of the most famous works by Tropinin is The Portrait of Alexander Pushkin. The poet was rather averse to sitting for portraits, and for that matter only two real life portraits – by Vasily Tropinin and Orest Kiprensky – have survived to this day. Contrary to the commonly-spread opinion that the portrait was commissioned by the poet’s friend, the bibliographer Sergei Sobolevsky, it was Pushkin who made that order, and later he gave the completed work to Sobolevsky, as a gift to be remembered by.