Vladimir Dubossarsky's artistic path began at the Moscow Art School in Memory of 1905, where he studied from 1980 to 1984, followed by further studies at the Surikov Moscow State Academic Art Institute. These formative years were essential in shaping his future artistic achievements.

Growing up in the family of the artist Efim Dubossarsky profoundly influenced Vladimir Dubossarsky's creative direction. He started gaining prominence in the art world during the Perestroika era, and his works have since been displayed in esteemed venues such as the Russian Museum, the Tretyakov Gallery, and the Centre Georges Pompidou in Paris.

Between 1994 and 2014, Vladimir Dubossarsky collaborated with Aleksandr Vinogradov in the art duo "Vindubi," creating works that heralded a new era in Russian art. Their joint canvases, a fusion of Socialist Realism, pop art, and kitsch, were notable for their imaginative storytelling and irony.

In addition to his painting career, Dubossarsky has been the mind behind "Art-Klyazma" since 2002. His innovative spirit was again on display in 2018 with a performance at the Udmurt Republican Museum of Fine Arts in Izhevsk.

Today, Vladimir Dubossarsky's works are found not only in major Russian and international museums but also in numerous private collections. Continuously active in Moscow, he remains a highly influential and recognized figure in contemporary Russian art, with his creative output attracting attention both within Russia and abroad.