In 1893, Woodruff was in the first U.S. presentation of
Brandon Thomas's ''
Charley's Aunt'', playing the part of Charley Wykeham. Over time he showed his range in Shakespeare, musical comedy, drama and farces. He appeared on stage with
Julia Marlowe,
William Collier Sr. and
Amelia Bingham. In 1901 he created the role Edward Warden in the original production of
Clyde Fitch's
The Climbers at the
Bijou Theatre. In 1902 he was in the cast of
Mary of Magdala with
Mrs. Fiske and
Rose Eytinge. In 1906 he scored a huge personal hit on Broadway in
Brown of Harvard. Woodruff had attended Harvard and the play was filmed several times. In 1915, Woodruff appeared in two silent films,
A Man and His Mate and
The Beckoning Flame, the latter apparently survives in the
Library of Congress. ==Membership of The Lambs==