Rosing was considered by many to rank as a singer and performer of the quality of Feodor Chaliapin. In his book The Perfect Wagnerite George Bernard Shaw called Chaliapin and Vladimir Rosing "the two most extraordinary singers of the 20th century."

Vladimir Rosing's recordings are best known for his performances of Russian art songs by composers such as Modest Mussorgsky, Nikolai Tcherepnin, Alexander Gretchaninov, Alexander Borodin and Nikolai Rimsky-Korsakov. He was the very first singer to record a song by Igor Stravinsky: Akahito from Three Japanese Songs.

As a stage director, Rosing championed the cause of opera in English, and he attempted to build permanent national opera companies in the United States and England. He directed opera performances "with such acumen and freshness of approach that some writers were tempted to speak of him as a second Reinhardt."

Rosing created his own system of stage movement and acting for singers that proved very effective in his own productions and that he also taught to a new generation of performers.

Rosing was born into an aristocratic family in St. Petersburg, Russia on January 23, 1890. His father was descended from a Swedish officer captured at the Battle of Poltava. His mother was the granddaughter of a Baltic Baron.

Rosing's parents separated when he was three, and his mother took Vladimir and his two older sisters to live in Switzerland. After four years they returned to Russia to live in Moscow near Rosing's godfather, General Arkady Stolypin, who was Governor of the Kremlin. For a time they lived at the Kremlin as the Governor's guests.

Rosing spent the summer of 1898 on his godfather's nearby country estate. There was a memorable trip with his mother to Yasnaya Polyana, the nearby estate of Leo Tolstoy, to meet the great writer. Tolstoy asked Rosing's mother to take a message to General Stolypin to give to the Tsar, but Stolypin later declined to do so.

The Tsar paid a visit to Moscow, and young Vladimir was taken to a performance of Tchaikovsky's opera Eugene Onegin, with the baritone Mattia Battistini, at the Bolshoi Theatre. The family sat in General Stolypin's box, while Tsar Nicholas II and his family occupied the Royal Box just a few feet away.

Rosing's parents reconciled the next year, and the family moved back to St. Petersburg. Rosing completed his studies at the Gymnasium (school) which lasted for eight years in Russia, and the family spent summers on their country estate in Podolia, Ukraine.

Russia was one of the biggest early markets for recorded music. Rosing's father brought home a gramophone in 1901, and Vladimir began to listen to and imitate the great singers of the day. He learned a repertoire of songs and arias, singing baritone as well as tenor parts. His real desire was to be a bass and sing Boito's Mefistofele, but nature had other plans for him.