David Wilcox was born in Montreal, Quebec, Canada, in the summer of 1949. He was only six when he sampled his first Elvis Presley music. The job that Presley had looked fun and exciting to young Wilcox. A year later, he was picking out tunes, or something like tunes, on a guitar. Before he was a teen, he managed to land his first gig.
In 1970, when he was 21, Wilcox got a little taste of fame as part of the Great Speckled Bird, a band that performed weekly on television. The show had a nationwide audience, and the band backed numerous big-star acts who appeared as guests. He also recorded with the band.
After a few years, Wilcox decided to move on and formed a band called the Teddybears, before trying his luck at performing solo, doing both blues-rock and roots rock at the time. In 1977, he recorded his debut album, Out of the Woods, and released it independently. Once he signed a deal with EMI Music Canada, the full-length album was re-released under the new label and hit the market in 1983. That same year, a sophomore offering arrived, My Eyes Keep Me in Trouble. It was followed a year later by Bad Reputation. Wilcox was building a good reputation, each album going gold.