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For two decades the Skydiggers have been integral members of Canada's vibrant folk-rock scene, garnering considerable critical acclaim and community support despite repeated industry setbacks and limited commercial success. Inspired to write songs after attending a concert by the Hi-Fi's (later Blue Rodeo) at the Cabana Club in Toronto, founding member Josh Finlayson formed an acoustic duo with Andy Maize in 1988, quickly attracting attention with their strong melodic vocal harmonies. With the additions of songwriter Peter Cash, drummer Wayne Stokes, and bassist Ron Macey, the Skydiggers rapidly became darlings of the Toronto club scene.
Less than a year after forming, the Skydiggers became the first signing of the new Canadian branch of Enigma Records, releasing their self-titled debut LP in 1990. Sales were modest but the record garnered two charting singles at Canadian radio, "Monday Morning" and "I Will Give You Everything," giving the group the foundation for the first of many Canadian cross-country tours. Despite their growing popularity, their new record company was unable to promote the album properly; soon the slim economics of the Canadian music marketplace and the collapse of the U.S. parent company forced Enigma Canada into bankruptcy. Undeterred, several former members of Enigma formed FRE Records, bankrolling and releasing the second Skydiggers album, Restless, in 1992. Critically acclaimed, Restless spawned their biggest hit single ("A Penny More") and is considered by many fans and critics as the high watermark of the band's recording career.
FRE and Enigma Records were then picked up for distribution by Capitol/EMI, which reissued the first album and released the album Just Over This Mountain in 1993, which ironically — after three records and a dozen tours of the country — helped earn the 1993 Juno Award for Most Promising Group of the Year. In 1995, the band signed to Warner Records, releasing Road Radio; simultaneously, FRE Records went bankrupt, discontinuing all of the band's back catalog. The lineup of the group also changed: most notably, Peter Cash left to form the Cash Brothers with his brother Andrew; only Finlayson and Maize have remained steadily part of the Skydiggers.
The next release, 1997's Desmond's Hip City, was released on the independent DROG Records label, and shows the band experimenting with a harder sound, and even features some slight trip-hop influences. In 1999, frustrated that their best-selling album, Restless, was still unavailable due to the legal limbo surrounding FRE's bankruptcy, the band independently released Still Restless: The Lost Tapes, assembling a newer version of the album around the original rehearsal tapes. Since then, they have also released There and Back (2000), a live recording from Toronto's Horseshoe Tavern on HipCity Records, the rootsy Bittersweet Harmony (2003 on Import Records), and an acoustic collaboration with the Cash Brothers (2006 on Maple Music).
Maize and Finlayson continue to tour Canada as a duo, as well as with established Canadian artists such as Blue Rodeo and Cowboy Junkies. Most notably, Andy Maize has used his many bad experiences with record labels to create a thriving independent Canadian record label and distributor, Maple Music, responsible for successfully releasing and promoting such Canadian artists as Paul Brandt, Tegan and Sara, Matthew Good, Loreena McKennit, Daniel Lanois, and Sarah Harmer.