Billboard Hot 100 chart with "Angel Eyes" and reached the Top 10 in Canada with the songs "I Think I Love You Too Much" and "How Long Can a Man Be Strong".

When he was 15, Healey formed the band Blue Direction,[4] a four-piece that primarily played bar-band cover tunes and featured bassist Jeremy Littler, drummer Graydon Chapman, and schoolmate Rob Quail on second guitar.

Healey began hosting a jazz and blues show on radio station CIUT-FM, where he was known for playing from his massive collection of vintage 78 rpm gramophone records.

The band made their first public appearance at the Birds Nest, located upstairs at Chicago's Diner on Queen Street West in Toronto.

[2] After being signed to Arista Records in 1988, the band released the album See the Light, which appeared on the RPM Top 100 chart in 1989.

[6] It featured the hit single "Angel Eyes" and the song "Hideaway", which was nominated for a Grammy Award for Best Rock Instrumental Performance.

Starting in 1990 he hosted a radio program of very early jazz on CIUT at the University of Toronto with Colin Bray.

He moved the show two years later to Jazz FM – CJRT; as a part of ongoing celebrations for what would have been Healey's 50th birthday in 2016, the latter program began to air in repeats Wednesdays 9pm on jazz.fm.

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.

Healey discovered and helped develop the careers of other musical artists, including Alex Pangman, Terra Hazelton, Amanda Marshall,[9] Shannon Curfman, and Philip Sayce[10] In early 2009, Healey's album Mess of Blues won in The 8th Annual Independent Music Awards for Best Blues Album.

[16] The 12 track Heal My Soul featured six covers and a number of collaborations with Marti Frederiksen, Arnold Lanni and Stevie Salas.