Healey began playing guitar when he was three, developing his unique style of playing the instrument flat on his lap. When he was 17, he formed the band Blue Direction, a four-piece band which primarily played bar-band cover tunes. Among the other musicians were bassist Jeremy Littler, drummer Graydon Chapman, and a schoolmate, Rob Quail on second guitar. This band played various local clubs in Toronto, including the Colonial Tavern.
Shortly thereafter he was introduced to two musicians, bassist Joe Rockman and drummer Tom Stephen, with whom he formed a trio, The Jeff Healey Band. This new band made their first public appearance at The Birds Nest, located upstairs at Chicago's Diner on Queen Street West in Toronto. They received a write-up in Toronto's NOW magazine, and soon were playing almost nightly in local clubs, such as Grossman's Tavern and the famed blues club Albert's Hall (where Jeff Healey was discovered by guitar virtuosos Stevie Ray Vaughan and Albert Collins).
After being signed to Arista Records in 1988, the band released the album See The Light, featuring the hit single "Angel Eyes" and the song "Hideaway", which was nominated for a "Best Instrumental" Grammy Award. While the band was recording See The Light, they were also filming (and recording for the soundtrack of) the Patrick Swayze film Road House. In 1990 the band won the "Entertainer of the Year" Juno Award. The albums Hell to Pay and Feel This gave Healey 10 charting singles in Canada between 1990 and 1994, including a cover of The Beatles' "While My Guitar Gently Weeps" which featured George Harrison and Jeff Lynne on backing vocals and acoustic guitar.
By the release of the 2000 album Get Me Some, Healey had grown weary of the world of rock music and began to concentrate his considerable talents in a direction closer to his heart, hot jazz.
He went on to release three CDs of music from this true passion, traditional American jazz from the 1920s and 1930s. He had been sitting in with traditional jazz bands around Toronto since the beginning of his music career. Though known primarily as a guitarist, Healey also played trumpet during live performances.
Healey was an avid record collector and amassed a collection of well over 30,000 78 rpm records. He had, from time to time, hosted a CBC Radio program entitled My Kind of Jazz, in which he played records from his vast vintage jazz collection. He hosted a program with a similar name on Toronto jazz station CJRT-FM, also known as JAZZ.FM91.
He had also been touring with his other group, 'The Jazz Wizards,' playing American 'hot' jazz. At the time of his death, they had been planning to perform a series of shows in Britain, Germany and Holland in April 2008.
For many years Healey performed at his club, Healey's on Bathurst Street in Toronto, where he played with a rock band on Thursday nights and with his jazz group on Saturday afternoons. The club moved to a bigger location at 56 Blue Jays Way and it was rechristened Jeff Healey's Roadhouse. (Though he had lent his name to the club and often played there, Jeff Healey did not own or manage the bar.) Healey also starred in the 1989 movie, "Road House" alongside Patrick Swayze.
Over the years he toured and sat-in with many legendary performers, including, Stevie Ray Vaughan, Buddy Guy, BB King, ZZ Top, Steve Lukather, Eric Clapton and many, many more. In 2006, Healey appeared on Deep Purple vocalist Ian Gillan's CD/DVD Gillan's Inn.
Healey discovered and helped develop the careers of other artists, including Amanda Marshall and Terra Hazelton.
On January 11, 2007, Healey underwent surgery to remove metastatic tissue from both lungs. In the previous eighteen months he had two sarcomas removed from his legs.
On March 2, 2008 Healey died of cancer at St. Joseph's Health Centre in his home town of Toronto; he was 41. His death came a month before the release of his new album, Mess of Blues, which was his first rock album in 8 years.
Healey is survived by his wife and two children.