Born in Brighton, Sussex in 1884, the nephew of Victorian era actor Edward Smith Willard, in 1920 Willard appeared in the plays of William Shakespeare at the Royal Shakespeare Theatre in Stratford-upon-Avon. He appeared in Hamlet, Twelfth Night, The Merchant of Venice, Richard III, and The Taming of the Shrew.
Willard's first film role was as the Fourth Party in A Window in Piccadilly (1928). His other film appearances include The Private Life of Don Juan (1934) with Douglas Fairbanks and Merle Oberon, The Scarlet Pimpernel (1934) with Leslie Howard and Raymond Massey, The Mystery of the Mary Celeste (1935) with Bela Lugosi, Van Zeeland in Rembrandt (1936) with Charles Laughton and Gertrude Lawrence, the Chief Steward in Underneath the Arches (1937) with Bud Flanagan, Chesney Allen and The Crazy Gang, the Chief of German Intelligence in Dark Journey (1937) with Vivien Leigh and Conrad Veidt, Hoots Mon! (1940) with Max Miller, Penn of Pennsylvania (1942) with Clifford Evans and Deborah Kerr, and The Young Mr. Pitt (1942) with Robert Donat and Robert Morley.