Vysotsky's parents were divorced soon after his birth, and he lived mostly with his mother (a technical translator), first in Buzuluk and then (from 1945) in Moscow. He attended the Institute of Civil Engineering for a year (1955–56) but quit to join the Nemirovich-Danchenko Studio School of the Moscow Art Theatre. He graduated in 1960 and became a professional actor, first at the Moscow Pushkin Dramatic Theatre and then at the Theatre of Miniatures (i.e., “Playlets”). From 1964 he was a member of the Moscow Theatre of Drama and Comedy on the Taganka, where he starred notably as Hamlet. He also was featured in several films and on television.

His great popularity as an actor was perhaps even exceeded by his popularity as a poet and songwriter; he wrote several hundred songs and poems, as well as incidental music for plays and films. Soviet officialdom permitted few of his songs to be sung on television or in films or to be recorded. His reputation spread by means of his appearances in clubs, factories, and universities and through the mass distribution of homemade (and illegal) tape recordings (magnitizdat) and typescripts and mechanical copies (samizdat). His lyrical themes ranged from Soviet prison life and internal exile (“Only the final judgment could be worse”) and Soviet official hypocrisy (“I grieve that honour has been put to rout, that backbiting has been deified”) to the exigencies of Russian daily life (crowded living quarters, long food lines, unfair privileges of the elite). More than simply reflecting a difficult reality, he gave many of his fellow citizens the strength to go on.

He died at age 42 of a heart attack brought on, it was said, by his hard-drinking lifestyle. In the late 1980s the Soviet government began allowing the publication of his poetry and song lyrics.