By the release of the 2000 album Get Me Some, Healey began to concentrate on jazz.
He went on to release three CDs of music of traditional American jazz from the 1920s and 1930s. He had been sitting in with these types of bands around Toronto since the beginning of his music career. Though known primarily as a guitarist, Healey also played trumpet during live performances. His main jazz group for touring and recording was Jeff Healey's Jazz Wizards.
Healey was an id record collector and amassed a collection of well over 30,000 78 rpm records. Starting in 1990 he hosted a radio program of very early jazz on CIUT at the University of Toronto with Colin Bray. Later he went national on CBC Radio's program entitled My Kind of Jazz, in which he played records from his vast vintage jazz collection. He moved the show two years later to Jazz FM – CJRT; as a part of ongoing celebrations for what would he been Healey's 50th birthday in 2016, the latter program began to air in repeats Wednesdays 9pm on jazz.fm.[10]
For many years, Healey toured throughout North America and Europe and performed at his club, "Healey's" on Bathurst Street in Toronto, where he played with his blues band on Thursday nights and also with his jazz group on Saturday afternoons. The club moved to a larger location at 56 Blue Jays Way and 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. (The name came from the 1989 film, Road House, in which Healey appeared.) At the time of his death, he had been planning to perform a series of shows in the United Kingdom, Germany, and the Netherlands, with his other band, the Jeff Healey Blues Band (aka the "Healey's House Band") in April 2008.
Over the years, Healey toured and sat in with many well-known performers, including The Allman Brothers, Bonnie Raitt, Stevie Ray Vaughan, Buddy Guy, B. B. King, ZZ Top, Steve Lukather, Eric Clapton and 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 musical artists, including Alex Pangman, Terra Hazelton, Amanda Marshall,[11] Shannon Curfman, and Philip Sayce[12]
In early 2009, Healey's album Mess of Blues won in The 8th Annual Independent Music Awards for Best Blues Album.[13]
In 2009, Healey was inducted into the Terry Fox Hall of Fame.
In June 2011, Woodford Park in Toronto was renamed Jeff Healey Park in his honour.[14]
In 2014, Healey was inducted into Canada's Walk of Fame. In September 2016, Jeff Healey was inducted into the Mississauga Music Walk of Fame.[15] In March 2016 the posthumous album Heal My Soul was released,[16] followed by the companion album Holding On in December of the same year.[17] Both records were compiled by Roger Costa from unreleased recordings.[18] The 12 track Heal My Soul featured six covers and a number of collaborations with Marti Frederiksen, Arnold Lanni and Stevie Salas.[19] The 15 track Holding On album contains ten live tracks recorded in 1999 at the Rockefeller Music Hall in Norway and five studio tracks.[20]