Biographers claim that his mother was a simple serf, while his father was a Russian landowner who freed his illegitimate son. Thanks to his talent and diligence, Orest Kiprensky, a product of the serf environment, became a beloved portraitist of the Russian public in the 19th century.

By the age of 23, Kiprensky achieved his first successes: for the painting "Dmitry Donskoy at Kulikovo Field," he received the Grand Gold Medal from the Academy, which allowed him to travel abroad at state expense.

Interestingly, Alexander Pushkin was usually dissatisfied with his portraits, but Orest Kiprensky became the only artist who managed to please the capricious poet. During Kiprensky's lifetime, the portrait of Pushkin became one of his most famous works and is still included in all literature textbooks. However, Kiprensky was long shy about his works and tried not to stand out among other masters.

A person from a serf background always found success at home insufficient, and his friends called him "mad Orest." After the end of military actions in Europe, he went to Italy, where he presented his works to the academicians. Europeans, upon seeing the portrait of Kiprensky's adoptive father Adam Shvalbe, accused him of passing off a work by Rubens or Van Dyck as his own. The academicians did not believe that such a masterpiece could be created by an artist from Russia. However, Kiprensky easily proved his talent and became the first Russian artist whose self-portrait was commissioned for the Uffizi Gallery in Florence.

The artist passed away in Rome on October 17, 1836, from pneumonia and was buried in the church of Sant'Andrea delle Fratte. A stele with the inscription was placed on his grave: "In honor and memory of Orest Kiprensky, the most famous among Russian artists, professor of the Imperial Petersburg Academy of Arts and member of the Neapolitan Academy, was erected at their own expense by Russian artists, architects, and sculptors, as many as were in Rome, mourning the prematurely extinguished light of their people and such a virtuous soul..."