In his teenage years, Hobbs continued to practice his craft, often writing and performing his own songs in the city while performing with other musicians and other groups. After high school, Hobbs received his journalism degree from Carlton University. In April 1994, he released his debut album, Under Your Feet, but the album received little fanfare. In 1996, while residing in Ottawa, Hobbs wrote and performed the music to a long-running play, Anarchy and the Dalmation. At the same time, he was performing with local group Hennessey. In 1999, he released Confused & Bleeding on Puddle Thief Music. The album was met with more praise and Hobbs became one of the "must-see" acts on the Toronto and Ottawa club circuit. In 2001, Hobbs performed at the North by Northeast Festival and released Drake Motel, which was produced by John Switzer, who worked with the Waltons and Jane Siberry, among others. The album garnered much praise for its combination of folk, country, and roots rock. Hobbs has also shared the stage with Bob Egan and Gregory Hoskins. ~ Jason MacNeil