Woodlock received a Bachelor of Arts degree from Yale College in 1969, where he was a member of Skull and Bones, and vice chairman of the "Yale Daily News". He began his career in journalism as an intern at the "Chicago Daily News", covering the 1968 Democratic National Convention in Chicago. Woodlock then became a reporter at the "Chicago Sun-Times" from 1969 to 1973, where he worked in Chicago and Springfield, Illinois, before moving to the "Sun-Times"s Washington Bureau in 1971–1973, where he covered the Supreme Court. Woodlock then attended Georgetown University Law Center, where he was a member of "The Georgetown Law Journal". He earned his J.D. in 1975.