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Cherkassky's first music lessons were from his mother, Lydia Cherkassky, who once played for Tchaikovsky in St. Petersburg.

She also taught the pianist Raymond Lewenthal.

In the United States, Cherkassky continued his piano studies at the Curtis Institute of Music under Josef Hofmann.

Before studying with Hofmann, however, Cherkassky auditioned for Sergei Rachmaninoff, who advised him to give up performing for at least two years and to change the position of his hands at the keyboard.

Conversely, Hofmann suggested Cherkassky should continue giving concerts, and this long association with public performance meant that Cherkassky felt comfortable before an audience.

Hofmann also recommended that he practice for four hours every day and Cherkassky did this religiously throughout his life, maintaining an extensive repertoire ( baroque to Berio ) to an exacting standard.

His studies and advisory sessions with Hofmann continued until 1935.

In the interim he began his lifelong obsession with world travel with trips to Australia, New Zealand, the Far East, Russia and Europe.