Olga Samaroff Stokowski was born Lucy Mary Agnes Hickenlooper in San Antonio, Texas, and grew up in Galveston. She went to study piano in Europe, where her teachers included Antoine François Marmontel at the Conservatoire de Paris and Ernst Jedliczka in Berlin. In Berlin, she made a brief first marriage to Boris Loutzky, a Russian engineer, but they were soon divorced. She returned to the USA and tried to launch a career as a pianist. Her agent suggested a professional name change to Olga Samaroff to boost her appeal. In 1905, she self-produced her New York debut at Carnegie Hall, the first woman ever to do so, and made a big impression with her performance of Tchaikovsky's Piano Concerto No. 1. She toured extensively in the USA and Europe and counted many artists and musicians among her friends, including George Gershwin, Irving Berlin, Dorothy Parker, and Cary Grant. In 1909, she played under Leopold Stokowski's direction when he made his conducting debut in Paris.
The couple married in 1911 and had a daughter. She made a number of early recordings and achieved the feat of performing all 32 Beethoven piano sonatas in public. In 1923, she and Stokowski divorced, and a couple of years later an injury forced her to retire from performing. She became a well-known critic and teacher, writing for the New York Evening Post among others, and gave lectures throughout the 1930s.
She taught at the Philadelphia Conservatory and in 1924, was invited to join the faculty of the newly-formed Juilliard School of Music in New York. She was called "Madam Samaroff" by her students, for whom she was a mentor and advocate. Her autobiography, An American Musician's Story, was published in 1939.