Vasily was born as a serf of Count Munnich in the village Korpovo of Novgorod guberniya and then transferred to Count Morkovs as a part of the Munichs daughters dowry. Soon he was sent to Saint Petersburg to study the trade of a confectioner. Instead of learning his trade Tropinin secretly attended free drawing lessons in the Imperial Academy of Arts.
In 1799, his owner allowed Tropinins to study at the Academy as a non-degree student (Postoronny uchenik). He took lessons from S. S. Schukin and was supported by the President of the Academy Alexander Sergeyevich Stroganov. In 1804 Tropinins work Boy Grieving for a Dead Bird was exhibited in the Academys exhibition and was noted by the Russian Empress at the time (most probably the Dowager Empress Maria Feodorovna).