Richard Woolley graduated in History from King's College, London in 1970 and attended the Royal College of Art between l970 and l973 where he was awarded a Master of Arts in Film & Television.
In l970 he co-directed (out of college) a 60 minute documentary We Who Have Friends that looked at the position of male homosexuals since the UK's l967 Reform Act.
In l973 he won a DAAD artist's endowment to work in West Berlin where he made three experimental films. His film Kniephofstrasse won a top prize at the Knokke-le-Zoute experimental Film Festival in l975.
In l976 Woolley took a break from film and moved over to theatre, working with the Red Ladder Theatre company as writer, musical composer and performer. He continued to work on and off for the company until 1980.