A future famous painter, graphic artist and illustrator, he got the first painting lessons from his father, the artist Boris Yankilevsky. From 1949 to 1956 Vladimir Yankilevsky studied at the Moscow High Art School under the Surikov Institute. In 1962 he graduated from the Polygraphic Institute.
In November, 1962 Vladimir Yankilevsky participated in a resonant exhibition titled Taganka as an independent artist. Several days later his works were presented at the exhibition The 30th Anniversary of the Moscow High Art School  in the Manege Exhibition Hall and were subjected to sharp criticism of Nikita Khrushchev.
In the years which followed this event Vladimir Yankilevsky worked as a graphic designer in publishing houses of Moscow to earn his living, and spent most of his time in the studio creating his drawings and paintings. For many years he had no opportunity to exhibit his works. In 1975 he participated in an exhibition in the Beekeeping Pavilion at the ENEA in Moscow. The year 1978 saw his first retrospective exhibition held in Moscow.
An original style developed by Vladimir Yankilevsky can be called epic expressionism. The series of works started in the early 1960s and integrated under the common title The Space of Experiences became the cornerstone of Vladimir Yankilevsky's art and an attempt of creating a picture of the play of universal powers through human experience. In this sense his seemingly "abstract" compositions are pshychological and therefore dramatic. The fundamental concept of his creativity took shape in those years. That is the Person against the Background of Eternity.
In the 1970s he created a series of Existential Boxes standing for the limited space of a person's existence - the contradiction between personal dreams and restrictions superimposed by the social environment. This became another key idea of the artist's approach.
Paintings and graphic art by Vladimir Yankilevsky were shown at 40 personal (in Moscow, St. Petersburg, New York, Bochum, Paris and London) and over 170 group exhibitions, including the exhibition RUSSIA! at the Guggenheim's Museum in New York in 2005.
Today Vladimir Yankilevsky's works are kept in the leading museums of Russia and the world, in particular, at the State Tretyakov Gallery, the State Russian Museum, the Pushkin Museum of Fine Arts, the Moscow Museum of Modern Art, Ludwig's Museums (Cologne, Budapest), Georges Pompidou's  Centre (Paris), the Dresden National Gallery, the Museum of Bochum City, the Zimmerli Museum (nonconformist art collection of Nancey and Norton Dodge, the USA), the Prague National Gallery, in the Athenes collection of George Kostaki, and many others.
Since 1989 Vladimir Yankilevsky has been living and working in New York, Paris and Moscow.