Lily Brayton married Oscar Asche, and the two of them collaborated often as actors and as managers. She made her first stage appearance in 1896 with Frank Benson's company. She remained with the troupe for some time, so as a "Bensonian" she played many roles in the plays of Shakespeare, appearing several seasons in the Stratford Shakespeare Festival. Her last appearance on the stage was as Portia in Julius Caesar.

Asche and Miss Brayton inscribed their names in the record book in 1916. Oscar Asche wrote a play entitled Chu-Chin-Chow in which he played the lead, Abu Hasan. The play broke all records when it ran for 2,238 performances. Miss Brayton took the part of Zahrat-al-Kulub and performed it almost 2,000 times during the run.