Drake began his career at nine years old when he became involved as a child actor in radio plays for the CBC in Vancouver.
At the age of 12, he and his family moved to the United States where he began singing professionally with the choir from St. Paul's Cathedral and later studied English literature at the University of California in Los Angeles.
During the 1960s, while working as an English teacher at a high school in San Diego, Drake wrote lyrics for The Kingston Trio and together with American actor Michael Storm, he co-founded The Good Time Singers, a folk group launched on The Andy Williams Show and released albums on the Capitol Records label.
In 1971, he returned to Canada and settled on a farm in the Canadian Rockies with his wife Sally and their three sons.
In 1975, Drake made his motion picture debut as both screenwriter and director of The Keeper, a low-budget Canadian horror film starring Christopher Lee which never received theatrical distribution; he also wrote the screenplay for the 1980 horror film Terror Train starring Jamie Lee Curtis.