With all of his maternal relatives musically inclined, the singer picked up the guitar at age 15 after his family disapproved of him owning a drum set. Growing up on a wide array of music, Wiley formed several high school rock bands before venturing out on his own. Spending a year away from home in Vancouver resulted in him returning to the island in 1998, but not before playing in bands called the Tubetracks and the Cawdaddies. In 1998 he also formed a trio dubbed the Evil Agents. In 2002, Wiley released his debut album Bottom Dollar, an album that earned him four East Coast Music Award nominations and ended up on various year-end lists in Canadian music circles. He also won CBC Radio's "Big Break" contest in the Atlantic Region the same year. The album drew Wiley comparisons to the likes of Tom Waits and Leonard Cohen. Touring in support of the album saw him share the stage with Steve Earle, Dan Bern, Sarah Harmer, and Blue Rodeo among others. In September 2004, Wiley released his sophomore album High Low on Warner Music. As with the first album Wiley produced all of the songs and played nearly all of the instruments. The album earned him four more East Coast Music Award nominations including male artist of the year and songwriter of the year. A tour in late 2004 with Ron Sexsmith and Sarah Slean also showcased his talents. The singer released a video for the title track and performed at the annual SXSW festival in Austin, TX, in March, 2005. ~ Jason MacNeil