Healey lost his sight at the age of one, after developing eye cancer. He began playing guitar when he was three years old and began performing with his band Blues Direction at the age of 17. Healey formed the Jeff Healey Band in 1985, featuring bassist Joe Rockman and drummer Tom Stephen. This trio released one single on its own Forte record label, which led to a contract with Arista Records. The Jeff Healey Band released their debut album, See the Light, in 1988 and the guitarist immediately developed a devoted following in blues-rock circles. Featuring the hit single "Angel Eyes," the record went platinum in the U.S. While the Jeff Healey Band's subsequent records were popular, none were as successful as the debut.

As the 21st century dawned, Healey began to change his direction. He taught himself to play the trumpet and began to lean toward the kind of traditional 1920s and '30s jazz that had always fascinated him. He released two classic jazz albums, 2002's Among Friends and 2004's Adventures in Jazzland, on his own HealeyOphonic label, and a third traditional jazz outing with It's Tight Like That, which appeared on Stony Plain in 2006. And while he continued to do shows in his earlier blues-rock style, he increasingly gigged with his jazz combo, the Jazz Wizards. In 2008, a month before the release of his last studio-recorded blues album, Mess of Blues, Healey died from cancer. Songs from the Road, a collection of live blues-rock performances from 2006 and 2007, was released by the Ruf imprint in 2009, nearly 18 months after Healey's death. His final studio jazz album, Last Call, was issued by Stony Plain in April 2010.