[3] He was a well-known lawyer – according to Alexander, especially popular among poor people, because he defended them for free and even helped financially, — and an occasional journalist (he published feuilletons under a pen name Graf Niver).

[6][7][8][9] Alexander's mother Eugenia Stepanovna Skolatskaya came from a noble family, but the parents rejected her after she had given birth to illegitimate children.

They didn't want siblings to meet, to the point that Alexander was told that his sister had died, and vice versa; only years later did he see her name in a theatrical magazine and contact her.

The novice performer was christened the "Russian Pierrot", gained renown, became an object of imitation, admiration, vilified in the press and lionized by the audiences.

His famous piece "Vashi paltsy pakhnut ladanom" ("Your Fingers Smell of Frankincense") was dedicated to another film star, Vera Kholodnaya.

Shortly before the October Revolution Vertinsky devised a stage persona of Black Pierrot and started to tour Russia and Ukraine performing decadent elegies with a touch of cosmopolitan chic, such as "Kokainetka" and Tango "Magnolia" ("V bananovo-limonnom Singapure").

In the words of the American historian Richard Stites, "Vertinsky bathed his verses in images of palm trees, tropical birds, foreign ports, plush lobbies, ceiling fans, and "daybreak on the pink-tinted sea"[11] — precisely those things which the war-time audience craved for.

In 1926, Vertinsky made one of the earliest recordings of the song "Dorogoi dlinnoyu" ("Дорогой длинною" or "Endless Road"), written by Boris Fomin (1900–1948) with words by the poet Konstantin Podrevskii,[12] which, with English lyrics by Gene Raskin, was a major hit for Mary Hopkin in 1968 as "Those Were the Days".

After several successful tours in the Middle East, Vertinsky followed the majority of well-to-do Russians to the United States, where he debuted before the audience which included Rachmaninoff, Chaliapin, and Marlene Dietrich.

To feed his family, he also appeared in Soviet films, often playing pre-revolutionary aristocrats, as in the screen version of Chekhov's "Anna on the Neck" (1955).

In 2021, an eight-episode television series about the singer, titled simply Vertinsky [ru], was premiered, first online and then on the Russian First Channel.