Over the course of thirty years the Skydiggers have formed a steady presence inside Canada’s lively folk-rock community, collecting extensive praise from reviewers and loyal grassroots backing even as they encountered multiple commercial roadblocks and only modest sales figures. After seeing a Hi-Fi’s performance—later known as Blue Rodeo—at Toronto’s Cabana Club, founding member Josh Finlayson was moved to begin composing and in 1988 launched an acoustic duo alongside Andy Maize that quickly drew notice for its rich vocal blend. Once songwriter Peter Cash, drummer Wayne Stokes and bassist Ron Macey joined, the Skydiggers soon became favorites on the Toronto club circuit.
Barely twelve months after their formation the group became the inaugural act signed to the fledgling Canadian division of Enigma Records and issued their self-titled debut LP in 1990. Although sales remained modest, two tracks—“Monday Morning” and “I Will Give You Everything”—entered the Canadian radio charts and supplied the base for the first of the band’s many national tours. Continued popularity could not offset the label’s promotional shortcomings; the constrained Canadian market combined with the American parent company’s collapse soon drove Enigma Canada into insolvency. Several ex-Enigma staffers promptly established FRE Records, which financed and released the Skydiggers’ sophomore effort, Restless, in 1992. Widely praised by critics, the album yielded the band’s biggest single to date, “A Penny More,” and is still regarded by many listeners and reviewers as the peak of their studio output.
Distribution rights for both FRE and Enigma subsequently moved to Capitol/EMI, which reissued the debut and brought out Just Over This Mountain in 1993—an album that, after three releases and numerous cross-country treks, ironically secured the 1993 Juno Award for Most Promising Group of the Year. The band moved to Warner Records in 1995 for Road Radio; at the same moment FRE Records folded, removing the entire back catalog from availability. Personnel shifts followed, most prominently Peter Cash’s departure to form the Cash Brothers with his sibling Andrew. Only Finlayson and Maize have remained constant, frequently touring Canada as a duo and also appearing alongside established acts such as Blue Rodeo and Cowboy Junkies. Drawing on his accumulated label frustrations, Maize launched the independent MapleMusic imprint and distribution company, which has successfully issued and promoted Canadian artists including Paul Brandt, Tegan and Sara, Matthew Good, Loreena McKennitt, Daniel Lanois and Sarah Harmer.
The next release, Desmond’s Hip City, arrived in 1997 on the independent DROG Records label and found the Skydiggers pursuing a tougher sound that incorporated traces of trip-hop. Frustrated that their strongest-selling album, Restless, remained unavailable because of legal entanglements from FRE’s bankruptcy, the band issued Still Restless: The Lost Tapes independently in 1999, rebuilding the record around original rehearsal tapes. There and Back, a live set captured at Toronto’s Horseshoe Tavern, surfaced in 2000, followed by the roots-oriented Bittersweet Harmony in 2003, a 2006 acoustic project with the Cash Brothers, and the studio album City of Sirens in 2008. A year later they surveyed their history with the 2009 anthology The Truth About Us: A Twenty Year Retrospective.
Returning in 2012, the Skydiggers delivered their eighth studio album, Northern Shore, on Latent Recordings, the label founded by Cowboy Junkies guitarist Michael Timmins. Recorded partly at Blue Rodeo’s Woodshed Studio and partly at the Tragically Hip’s Bathhouse, the set featured a guest appearance by the returning Peter Cash. The holiday collection Angels appeared two years afterward, after which the group turned to the catalog of Byrds singer-songwriter Gene Clark for 2016’s Here Without You. In 2017 they issued the Timmins-produced Warmth of the Sun, which included the singles “Apology,” “When You’re on a Roll” and “Needle and Thread.”
