information:highlighting, stylistic:tone, structural:summarization
Themes

Vysotsky's songs—over 600 of them—were written about almost any imaginable theme. The earliest were blatnaya pesnya ("outlaw songs"). These songs were based either on the life of the common people in Moscow or on life in the crime people, sometimes in Gulag. Vysotsky slowly grew out of this phase and started singing more serious, though often satirical, songs. Many of these songs were about war. These war songs were not written to glorify war, but rather to expose the listener to the emotions of those in extreme, life-threatening situations. Most Soviet veterans would say that Vysotsky's war songs described the truth of war far more accurately than more official "patriotic" songs.

Nearly all of Vysotsky's songs are in the first person, although he is almost never the narrator. When singing his criminal songs, he would adopt the accent and intonation of a Moscow thief, and when singing war songs, he would sing from the point of view of a soldier. In many of his philosophical songs, he adopted the role of inanimate objects. In essence, Vysotsky's songs were miniature theatrical dramatizations, often with a protagonist and containing many dialogues. He achieved such a high level of authenticity that many real life former prisoners, war veterans, boxers, and footballers refused to believe that Vysotsky had not himself spent time behind bars, fought in the war, or been a boxer or footballer. Following his first solo concerts at the Leningrad Nuclear Physics Institute, he published a note for his fans with the words: "Now that you've heard all these songs, please, don't you make a mistake of mixing me with my characters, I am not like them at all. With love, Vysotsky, 20 April 1965, XX c." He found it necessary to make similar excuses throughout his career.

Veteran screenwriter Nikolay Erdman said of Vysotsky's work: "I can well understand how Mayakovsky or Seryozha Yesenin did it. How Volodya Vysotsky does it is totally beyond me."

However, one of the themes in his repertoire was considerably more autobiographical: alcoholism, with which he personally struggled. By the time of his breakthrough in 1967, he had already suffered several physical breakdowns, and once was sent (by the director of the Taganka Theatre) to a rehabilitation clinic, a visit he had to repeat multiple times thereafter.