During his high school years, Conway, along with his brother Mic, attended Camberwell High School. Conway was a member of the Conway Brothers Hiccups Orchestra from 1984–1988 and toured the UK in 1986 appearing at the Edinburgh Festival, the Capitol Music Festival and the Newcastle Festival. In 1988, the Conway Brothers appeared at the Houston International Festival, World Expo 88 and the Perth festival. Conway joined the Backsliders in 1989, touring nationally at festivals including the Perth, Adelaide, Sydney, Brisbane and Melbourne Festivals, Womad, the East Coast Blues Festival, the Port Fairy Folk Festival, the Wangaratta Jazz Festival, the Bellingen Jazz Festival and the Gold Coast International Jazz and Blues Festival. He has twice been a judge at the Hohner Australian Harmonica Championships at the Tamworth Country Music Festival. Apart from four successful recordings, including two gold records with Captain Matchbox, Conway co-produced two of the Backsliders eight albums; "Sitting on a Million" and "Hellhound". In 2003 he produced a recording funded by the Australia Council for his band "Big Wheel". The resulting recording, 'Little Story' was nominated in the Blues & Roots category for the 2004 ARIA awards. Conway is a sought after session musician and has recorded with numerous artists including Shane Howard Colin Hay, Jon Lord, Bob Brozman, Slim Dusty, Jan Preston, Tim Gaze, Dutch Tilders, Anne Kirkpatrick and Pat Drummond. During 2007 and 2008 he recorded and performed with The Brewster Brothers of The Angels fame. Conway has also composed, produced and recorded music for a broad range of film and radio projects, including the Kennedy Miller telemovieThe Riddle of the Stinson and the comedy feature The Honourable Wally Norman which was chosen to open the 2003 Sydney Film Festival. The Jim Conway Blues, a documentary film celebrating Conway's contribution to Australian music was screened on S.B.S. Television in July 2000. The film won a silver medal for Best Independently Produced Documentary at the Chicago International Film Festival. A photographic portrait of Conway by renowned photographer Greg Weight won the inaugural Prize for Photographic Portraiture associated with the Archibald Prize. In 2003 he was awarded the prestigious Centenary Medal in recognition of his contribution to the Arts. Conway was diagnosed with multiple sclerosis in 1983 and as a result has been confined to a wheelchair for a number of years. At the Sydney ParalympicsOpening Ceremony he performed a piece of music specially written to feature his harmonica playing. Due to his increasing disability he announced his retirement from performing in 2014.