[2] Woolf's film credits include San Ferry Ann (1965), Marat/Sade (1967), Tell Me Lies (1968), The Lion in Winter (1968), Great Catherine (1968), The Bed Sitting Room (1969), Alfred the Great (1969), The Ruling Class (1972), The Love Pill (1972), Galileo (1975), The Rocky Horror Picture Show (1975), Rogue Male (1976), The Hound of the Baskervilles (1978), Gorky Park (1983), Superman III (1983), and Maid to Order (1987).

On British television, Woolf played the Man in Harold Pinter's one-man play Monologue (1973); parts in Rutland Weekend Television (1975–1976) and The Sweeney (1975); the Collector in the Doctor Who serial The Sun Makers (1977); served as the host of the 1970s pre-school British educational series Words and Pictures; and performed the role of Doctor Cornelius in the BBC adaptation of Prince Caspian (1989).

[3] He served as artistic director of the annual summer Shakespeare on the Saskatchewan festival, in Saskatoon, from 1991[4] until his retirement from that position in 2001.

In March 2003, Woolf directed an all-female production of Twelfth Night, by William Shakespeare, at the University of Winnipeg.

[8] In 1978, with his wife, actress/director Susan Williamson, whom he married in 1968, Woolf moved to Canada where he took a teaching position at the University of Alberta Drama Department.